Halogen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/425)
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Patent number: 6284154Abstract: Novel phenylcyclohexanes of the formula I in which n is 0 to 7, Q1 and Q2 are H, or one of these radicals is alternatively CH3, r is 0, 1, 2, 3, 4 or 5, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or a single bond, X is F, Cl, —CF3, —CN, —OCF3 or —OCHF2, and Y and Z are each, independently of one another, H or F, with the proviso that, in the case where A is a single bond, Q1═Q2═H and simultaneously X═CN, Y and/or Z are F.Type: GrantFiled: June 7, 1995Date of Patent: September 4, 2001Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Andreas Wächtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
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Patent number: 6214999Abstract: The present invention relates to a process for the preparation of 4′-bromomethyl-biphenyl derivatives of the formula: by reacting a 4′-methyl-biphenyl derivative of the formula: with a brominating agent a in a hydrobromic acid/alkali metal bromate system in a two-phase medium, and under photo-iradiation, where R is as defined in the specification.Type: GrantFiled: July 14, 2000Date of Patent: April 10, 2001Assignee: Sanofi-SynthelaboInventors: Michel Biard, Bertrand Castro
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Patent number: 6211399Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst at a temperature of ambient to about 100° C. and a pressure of about 10 to about 100 psig.Type: GrantFiled: October 5, 1999Date of Patent: April 3, 2001Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, David C. Johnson
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Patent number: 6187945Abstract: An industrially advantageous process for producing cyanobenzyl compounds under mild conditions from relatively easily available cyanobenzylamine having a cyano group on the benzene ring or a compound thereof which is ring-substituted with a chlorine atom, a fluorine atom, etc. The process for producing a cyanobenzyl compound includes transforming an aminomethyl group of a cyanobenzylamine compound into a hydroxymethyl group, a halogenomethyl group, or an acyloxymethyl group without causing damage to a cyano group on the benzene ring. The transformation may be carried out by use of nitrosonium ions.Type: GrantFiled: November 24, 1999Date of Patent: February 13, 2001Assignee: Showa Denko K.K.Inventors: Hiroshi Yasuda, Masatoshi Murakami
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Patent number: 6172225Abstract: The invention relates to a novel process for producing thereof hydroxyarenes of the general formula (I) in which n represents the numbers 1, 2, 3 or 4, R represents cyano, carboxyl, formyl, nitro, halogen or represents alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl or alkoxycarbonyl, each of which is optionally substituted, and Z represents hydrogen, cyano, nitro, halogen, alkyl, halogenoalkyl, or represents monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino, each of which is optionally substituted, characterized in that halogenoarenes of the general formula (II) in which n, R and Z are each as defined above and X represents halogen are reacted with 3-hydroxy-propionitrile of the formula (III), HO—CH2CH2—CN (III), if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, at temperatures between 0° C. and 100° C.Type: GrantFiled: November 12, 1998Date of Patent: January 9, 2001Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Linker, Wilhelm Haas, Otto Schallner, Kurt Findeisen, Roland Andree, Mark Wilhelm Drewes
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Patent number: 6166242Abstract: The invention concerns a method for producing compound containing fluorine, particularly fluorobenzaldehyde and fluorobenzonitrle, by a halogen exchange reaction with a compound of the formula I as fluorinating agent, defined in the specification, and a quatenary aminophosphonium compound of the formula III as catalyst, as defined in the specification, and in a solvent consisting of a nitro and/or sulfoxy substituted organic compound of the formula IVa and/or IVb, as defined in the specification.Type: GrantFiled: February 28, 2000Date of Patent: December 26, 2000Assignee: Aventis Research & Technologies GmbH & Co KGInventors: Wolfgang Appel, Sergej Pasenok, Thomas Wessel
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Patent number: 6149837Abstract: Provide is a novel phenylacetylene compound (1) which has a large anisotropy of refractive index, tends to be mixed with other liquid crystals, and is more advantageous in stability to light, a liquid crystal composition and a liquid crystal element usable for an optical shutter, a display element, ##STR1## A.sup.1 to A.sup.12 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 10 carbon atoms, and at least one is an alkyl group.Type: GrantFiled: February 25, 1999Date of Patent: November 21, 2000Assignees: Sumitomo Chemical Company, Limited, Agency of Industrial Science and Technology, New Energy and Industrial Technology Development OrganizationInventors: Chizu Sekine, Koichi Fujisawa, Naoto Konya, Masayoshi Minai
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Patent number: 6133468Abstract: Substituted benzyl bromides of the formula I ##STR1## where at least one substituent R.sup.1-5 is an electron-attracting group such as fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano or nitro, and the other substituents R.sup.1-5 are hydrogen or methyl,are prepared by bromination of substituted toluenes of the formula II ##STR2## with a brominating agent at from 20 to 95.degree. C.Type: GrantFiled: January 11, 2000Date of Patent: October 17, 2000Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Norbert Gotz, Michael Keil, Bernd Muller
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Patent number: 6118018Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.Type: GrantFiled: December 6, 1999Date of Patent: September 12, 2000Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
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Patent number: 6111114Abstract: The compounds of the formula (I) wherein R is as defined in the disclosure, are prepared by bromination of compounds of the formula (II) by means of Br.sub.2 or HBr in the presence of H.sub.2 O.sub.2.Type: GrantFiled: October 19, 1999Date of Patent: August 29, 2000Assignee: Istituto Luso Farmaco D'Italia S.p.A.Inventors: Aldo Salibeni, Renato Canevotti
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Patent number: 6020517Abstract: A process for producing a fluorinated benzonitrile comprising hydrogenolyzing a fluorinated dicyanobenzene substituted with 1 to 4 fluorine atoms and having the remainder which may be substituted with a chlorine atom in the presence of a catalyst to cause hydrodecyanation of only the cyano group of one side and a process for producing a fluorinated benzyl alcohol comprising reducing the fluorinated benzonitrile and hydrolyzing the fluorinated benzonitrile and reducing the resultant corresponding fluorinated benzoic acid to convert the cyano group to a hydroxymethyl group.Type: GrantFiled: April 27, 1998Date of Patent: February 1, 2000Assignee: Showa Denko K.K.Inventors: Hiroyuki Monzen, Katsutoshi Morinaka, Hideo Miyata, Tsutomu Nozawa, Haruaki Ito, Kohei Morikawa
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Patent number: 6017467Abstract: A propiolonitrile derivative of formula (I) ##STR1## wherein n1 and n2 each independently stand for 0 or 1; A1, A2 and A3 each independently represent a 1,4-phenylene, a 1,4-phenylene substituted by one or more fluorine atoms, a trans-1,4-cyclohexylene, a 1,3-dioxane-2,5-diyl or a 1,3-pyrimidine-2,5-diyl; Z1, Z2 and Z3 each independently represent a single bond, ethylene, ethenylene, ethynylene, carbonyloxy, oxycarbonyl, methyleneoxy, oxymethylene, 1,4-butylene or 1,4-butenylene; R represents a saturated, aliphatic hydrocarbyl radical of 1-10 carbons, an unsaturated, aliphatic hydrocarbyl radical of 2-10 carbons, a saturated or unsaturated, aliphatic hydrocarbyl radical of 1-10 carbons containing one or more ether linkages (--O--) in the chain and a saturated or unsaturated, fluoro-substituted aliphatic hydrocarbyl radical of 1-10 carbons containing one or more fluorine atoms in the chain; X1 and X2 each independently represent H, F or Cl;provided that at least one of X1 and X2 is F or Cl, when both n1 and n2Type: GrantFiled: June 13, 1997Date of Patent: January 25, 2000Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Hiroyuki Takeuchi, Kazutoshi Miyazawa, Norio Tamura, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 5981789Abstract: Disclosed is a method of preparing an aromatic compound having the general formula ##STR1## where R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1, or 2, n is 0, 1, or 2, q is 1 or 2, and q+m+n is an integer from 1 to 5. A vapor is prepared of a substrate having the general formula ##STR2## and a chlorinating agent. The mixture is reacted at a temperature above the boiling point of the substrate but below its decomposition temperature. The amount of chlorinating agent is about 0.5 to about 2 times the amount stoichiometrically required to replace the nitro groups on the substrate with chlorine. Unreacted substrate and partially reacted substrate are condensed from the product mixture and are recycled. The substrate is preferably in contact with the chlorinating agent before it is vaporized.Type: GrantFiled: December 30, 1998Date of Patent: November 9, 1999Assignee: Occidental Chemical CorporationInventors: John Hickey, Robert L. Bell, George Piotrowski
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Patent number: 5977397Abstract: Disclosed is a method of removing an acid halide, anhydride, or ester impurity from a mixture with a desired product with which it codistills. At least about a stoichiometric amount of a primary or secondary amine having a boiling point at least 10.degree. C. higher or lower than the boiling point of said desired product is added to the mixture. The desired product is not an acid halide, anhydride, or ester and does not react with the amine. The amine forms a reaction product with the impurity that has a boiling point at least 10.degree. C. higher or lower than the boiling point of the desired product. The mixture is distilled to isolate the desired product.Type: GrantFiled: April 14, 1999Date of Patent: November 2, 1999Inventor: Ronald Spohn
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Patent number: 5976408Abstract: An acrylonitrile derivative expressed by the following general formula I, a composition comprising the derivative and having an improved viscosity and optical anisotropy, and a liquid crystal display device: ##STR1## wherein rings A.sup.1 to A.sup.3 represent phenylene, cyclohexylene, dioxane, or pyrimidine, R.sup.Type: GrantFiled: December 19, 1997Date of Patent: November 2, 1999Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Koichi Shibata, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5942648Abstract: Naphthalene derivatives of the fomula I ##STR1## in which: R.sup.1 is an alkyl or alkenyl radical which is unsubstituted, monosubstituted by CH or CF.sub.3 or monosubstituted by halogen and has 1 to 15 carbon atoms, it also being possible for one or more CH.sub.2 groups in these radicals to be replaced, in each case independently of one another, by --O--, --S--, ##STR2## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a manner that oxygen atoms are not linked directly to one another, ##STR3## m is 0, 1 or 2, n is 0 or 1, wherem+n is 1 or 2,Z.sup.1 and Z.sup.2 are each, independently of one another, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or a single bond,L.sup.1 and L.sup.2 independently of one another, are H or F,x is an alkyl or alkoxy radical which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted bi halogen and has 1 to 15 carbon atoms, or is OH, CN, SCN, OCN, NCS or Q--Y,whereQ is a single bond, (CF.sub.2).sub.r or O(CF.sub.2).sub.Type: GrantFiled: March 4, 1997Date of Patent: August 24, 1999Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: David Coates, Mark Goulding, Simon Greenfield, Volker Reiffenrath, Reinhard Hittich, Herbert Plach
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Patent number: 5910617Abstract: The process according to the invention consists in preparing chlorides of aliphatic or cycloaliphatic hydrocarbons by reacting the corresponding mono- or polyalcohol with phosgene or thionyl chloride in the presence of at least one catalyst chosen from hexasubstituted guanidinium halides and their hydrohalides, optionally grafted via one of their radicals to a silica-based support.The chlorides are quickly obtained with good yields and contain few by-products such as carbonates or chloroformates.Type: GrantFiled: June 18, 1998Date of Patent: June 8, 1999Assignee: Societe Nationale Des Poudres Et ExploisfsInventors: Loic Lecomte, Serge Metge, Denis Souyri
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Patent number: 5891360Abstract: Novel phenylcyclohexanes of the formula I ##STR1## in which n is 0 to 7, Q.sup.1 and Q.sup.2 are H, or one of these radicals is alternatively CH.sub.3, r is 0, 1, 2, 3, 4 or 5, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or a single bond, X is F, Cl, --CF.sub.3, --CN, --OCF.sub.3 or --OCHF.sub.2, and Y and Z are each, independently of one another, H or F, with the proviso that, in the case where A is a single bond, Q.sup.1 =Q.sup.2 =H and simultaneously X=CN, Y and/or Z are F.Type: GrantFiled: April 15, 1993Date of Patent: April 6, 1999Assignee: Merck Patent Gesellschaft MIT BeschrankterInventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
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Patent number: 5866709Abstract: Disclosed is a process for making an aromatic nitrile by reacting a benzotrichloride with an ammonium halide in the presence of an oxygen-donating initiator at a temperature of about 150.degree. to about 250.degree. C. An optional catalyst of a metal oxide or a metal salt can be used if desired.Type: GrantFiled: December 2, 1997Date of Patent: February 2, 1999Assignee: Occidental Chemical CorpInventors: Michael C. Hausladen, Bao-Guo Huang, David Y. Tang
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Patent number: 5856557Abstract: A 2,2',5,5',6,6'-hexafluorobiphenyl-3,3',4,4'-tetracarboxylic acid precursor as an intermediate material for a highly functional fluororesin may be produced at a high yield by reacting tetrafluorophthalonitrile with an alkali metal iodide.Type: GrantFiled: June 12, 1997Date of Patent: January 5, 1999Assignee: Ube Industries, Ltd.Inventors: Yumiki Noda, Takashi Honma
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Patent number: 5841001Abstract: The present invention provides an industrially advantageous process for the preparation of an optically active 2-halo-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or as intermediates thereof; and a simple process for the preparation of an optically active substituted styrene oxide or 2-amino-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or intermediates thereof. A 2-halo-1-(substituted phenyl)ethanol represented by the following general formula (I) is allowed to contact, in the presence of a carboxylic anhydride, with an enzyme stereoselectively catalyzing ester interchange to produce an optically active 2-halo-1-(substituted phenyl)ethanol: ##STR1## (wherein X represents a chlorine atom or a bromine atom, and R.sup.1, R.sup.2 and R.sup.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a C.sub.1-5 alkyl group, a C.sub.1-5 haloalkyl group, a C.sub.Type: GrantFiled: February 28, 1997Date of Patent: November 24, 1998Assignee: Mitsubishi Chemical CorporationInventors: Ken Tanaka, Mari Yasuda, Makoto Ueda
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Patent number: 5824817Abstract: The invention relates to the use of the known compound 2,6-dichloro-3-fluoro-benzonitrile as active compound in selectively-herbicidal compositions, and to new preparation processes and new intermediates for the preparation of this compound.Type: GrantFiled: July 28, 1997Date of Patent: October 20, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Werner Bussmann, Josef Kasbauer, Markus Dollinger, Hans-Joachim Santel
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Patent number: 5789582Abstract: A nuclear halogenated aromatic compound possessing cyano groups is produced by a method using as a raw material an aromatic compound which possesses cyano groups and assumes a solid state at room temperature and subjecting the raw material to a procedure comprising a step of melting and transporting the compound by a means transport-melting, a step of vaporizing the compound, a step of mixing the compound with a halogen gas, and a step of causing the vapor of the compound to react with the halogen gas in vapor phase in the presence of a catalyst sequentially in the order mentioned, which comprises maintaining a content of a self-condensate of the aromatic compound possessing cyano groups which arise during the melting of the aromatic compound possessing cyano groups in a gas of the compound which reacts with the halogen gas to a level of not more than 2.5 mol % based on the compound.Type: GrantFiled: March 7, 1997Date of Patent: August 4, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Osamu Kaieda, Koichi Hirota, Teruhisa Kajiwara, Norimasa Okuda, Hisakazu Shindo, Yoshiro Hanayama, Yujin Shoda, Toyohiko Kohno, deceased, Takashi Yodoshi, Masaru Awashima
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Patent number: 5777181Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.Type: GrantFiled: April 10, 1996Date of Patent: July 7, 1998Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5760280Abstract: A process for producing aromatic compounds comprises the step of carrying out a reaction between an aromatic carboxylic acid and a polyfluorobenzonitrile, thus forming an aromatic nitrile and a polyfluorobenzene. This process can produce the aromatic compounds with few problems with respect to worker safety and at a low cost when compared with conventional processes, and can convert the starting materials for the reaction into useful substances with ease and little waste and in a high yield.Type: GrantFiled: May 16, 1997Date of Patent: June 2, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Isamu Maeda, Hiroshi Sugizawa, Noboru Saito
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Patent number: 5755994Abstract: A novel liquid crystalline compound having a large dielectric anisotropy value, a small change in the threshold voltage depending upon temperatures, and an improved solubility in other liquid crystal materials at low temperatures, and a liquid crystal composition containing the compound are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R is H or an alkyl group of 1 to 10C; l is an integer of 1 to 9; m, n and o are each independently 0 or 1; A.sub.1, A.sub.2 and A.sub.3 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, one or more H atoms on the ring of which group may be replaced by F, or the like group; Z.sub.1, Z.sub.2 and Z.sub.3 are each independently --COO--, etc., but at least one of them is --COO--; X is CF.sub.3, etc.; and Y.sub.1, and Y.sub.2 are each independently H or F.Type: GrantFiled: February 22, 1996Date of Patent: May 26, 1998Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Yasuyuki Koizumi, Koichi Shibata, Yasuhiro Haseba, Norihisa Hachiya, Etsuo Nakagawa, Kazutoshi Miyazawa
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Patent number: 5756834Abstract: It is known to prepare fluorinated aromatic compounds of the formula I ##STR1## in which X, Y and Z can have the meaning specified in the description, by reacting aromatic compounds of the formula II ##STR2## in which X, Y and Z have the meaning specified for formula I, with fluorine in a reaction medium.According to the invention, the direct fluorination is carried out in a reaction medium containing polyfluoroalkanesulfonic acids of the formula IIICF.sub.n H.sub.3-n (CFY).sub.m --SO.sub.3 H (III)in whichm, n and Y have the meaning specified in the description.By this means, it is possible, particularly advantageously to provide a process, which improves the known processes not only with regard to the selectivity and the yield, but also with respect to the quality of the resulting products of the process in a manner not readily predictable.Fluorinated aromatic compounds of the formula I as intermediates for active compound synthesis.Type: GrantFiled: November 7, 1996Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Sergej Pasenok, Wolfgang Appel
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Patent number: 5756806Abstract: The present invention provides a compound represented by the general formula (I): ##STR1## wherein X represents Cl or Br, a process for preparation of the same and a process for preparation of 3-substituted benzisothiazole by reaction of the compound (I) with a piperazine compound.Type: GrantFiled: May 21, 1997Date of Patent: May 26, 1998Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Junichi Sakamoto, Shigeki Sakaue, Sakae Kajihara, Miki Todo
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Patent number: 5750731Abstract: A perfluorinated aromatic compound represented by general formula (7): ##STR1## wherein R.sub.3 is a tetravalent perfluorinated aromatic group represented by formula (8): ##STR2## wherein (R.sub.4)s are the same, each being a carboxyl group or a cyano group, or two adjacent (R.sub.4)s combine to form a divalent group represented by formula (10): ##STR3## provided that when R.sub.4 is a cyano group, R.sub.3 denotes said tetravalent perfluorinated aromatic group represented by formula (9).Type: GrantFiled: September 20, 1996Date of Patent: May 12, 1998Assignee: Nippon Telegraph & Telephone CorporationInventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
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Patent number: 5744058Abstract: Dienes of the formula I ##STR1## in which n is 0, 1, 2, 3, 4 or 5,r is 1, 2 or 3,s is 1 or 2, ##STR2## is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl, ##STR3## is trans-1,4-cyclohexylene, trans-1,3-dioxane-2,5-diyl, unfluorinated or mono- or polyfluorinated 1,4-phenylene, in which one or two CH groups may also be replaced by N, or the central part ##STR4## Z is a single bond, a bridging member selected from the group consisting of --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CO--O--, --CH.sub.2 O--, --OCH.sub.2 -- and --O--CO--, or any desired combination of two such bridging members, where two O atoms are not linked directly to one another, andR is --CN, --NCS, halogen or an alkyl, alkenyl, alkoxy or alkenyloxy group, in each case having up to 12 carbon atoms and in each case unsubstituted or monosubstituted or polysubstituted by fluorine and/or chlorine.Type: GrantFiled: June 2, 1995Date of Patent: April 28, 1998Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Bernhard Rieger
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Patent number: 5734073Abstract: A method of halogenating an aromatic compound which comprises the steps of reacting an halogenating agent with the aromatic compound in the presence of fluorine and an acid, wherein the halogenating agent is at least one of an iodinating agent, a brominating agent and an chlorinating agent.Type: GrantFiled: April 18, 1996Date of Patent: March 31, 1998Assignee: BNFL Fluorochemicals LtdInventors: Richard Dickinson Chambers, Christopher John Skinner, Malcolm John Atherton, John Stewart Moilliet
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Patent number: 5679827Abstract: The present invention provides a compound represented by the general formula (I): ##STR1## wherein X represents Cl or Br, a process for preparation of the same and a process for preparation of 3-substituted benzisothiazole by reaction of the compound (I) with a piperazine compound.Type: GrantFiled: April 10, 1996Date of Patent: October 21, 1997Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Junichi Sakamoto, Shigeki Sakaue, Sakae Kajihara, Miki Todo
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Patent number: 5639887Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.Type: GrantFiled: May 25, 1995Date of Patent: June 17, 1997Assignee: American Cyanamid CompanyInventors: Dennis Powell, Rolf Paul, William A. Hallett, Dan M. Berger, Minu D. Dutia
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Patent number: 5621147Abstract: A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1):R--(A).sub.m --Cy--CF=CF.sub.2 (1)wherein R is a C.sub.1-10 alkyl group, a halogen atom or a cyano group, provided that in the case of the alkyl group, an oxygen atom may be interposed in a carbon-carbon bond of the alkyl group or in a carbon-carbon bond between this alkyl group and A, some of carbon-carbon bonds in the alkyl group may be triple bonds or double bonds, one --CH.sub.2 -- group in the alkyl group may be substituted by a carbonyl group, and some or all of hydrogen atoms in the alkyl group may be substituted by fluorine atoms;Cy is an unsubstituted trans-1,4-cyclohexylene group;A is a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a 1,4-cyclohexenylene group, wherein each of such cyclic groups is unsubstituted or substituted by one or more halogen atoms or cyano groups, one or more =CH-- groups constituting rings of such cyclic groups may be substituted by nitrogen atoms, and one or more --CH.sub.Type: GrantFiled: May 4, 1995Date of Patent: April 15, 1997Assignee: Asahi Glass Company Ltd.Inventors: Osamu Yokokoji, Tamaki Simizu, Seisaku Kumai
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Patent number: 5597825Abstract: The invention relates to biphenyl derivatives of general formula ##STR1## wherein A to E and X are defined as in claim 1, the stereoisomers thereof, including their mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties, preferably aggregation-inhibiting effects, pharmaceutical compositions containing these compounds and processes for preparing them.Type: GrantFiled: May 16, 1994Date of Patent: January 28, 1997Assignee: Dr. Karl Thomae GmbHInventors: Frank Himmelsbach, Helmut Pieper, Volkhard Austel, G unter Linz, Thomas M uller, Wolfgang Eisert, Johannes Weisenberger
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Patent number: 5565612Abstract: The present invention relates to substituted 2-chloro-3,4,5-trifluorobenzenes of the formula ##STR1## in which R is NO.sub.2, NH.sub.2, CN or Cl, and to a process for the preparation of substituted 2-chloro-3,4,5-trifluorobenzenes of the formula given above, in which R is NO.sub.2, NH.sub.2, CN, Cl or Br, which involves reacting 2,3,4-trifluorochlorobenzene with a nitrating agent in the presence or absence of a water-insoluble solvent at from -10.degree. C. to 50.degree. C., reducing 2-chloro-3,4,5-trifluoronitrobenzene or a mixture which contains 2-chloro-3,4,5-trifluoronitrobenzene and 5-chloro-2,3,4-trifluoronitrobenzene, in the presence of an organic solvent, isolating 2-chloro-3,4,5-trifluoroaniline or a mixture which contains 2-chloro-3,4,5-trifluoroaniline and 5-chloro-2,3,4-trifluoroaniline, diazotizing this product, if desired, and exchanging the diazotized group for a chloride atom, bromide atom or cyanide radical.Type: GrantFiled: May 5, 1995Date of Patent: October 15, 1996Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Thomas Schach
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Patent number: 5502235Abstract: A process for making 2,6-difluorobenzonitrile, comprising reacting 2,6-dichlorobenzonitrile with a substantially anhydrous metal fluoride at a temperature between about 160.degree. C. and about 300.degree. C. and in the presence of a phase transfer catalyst, which is typically a polyether, tetra-substituted phosphonium salt, tetra-substituted ammonium salt, and cryptand, but in the absence of a solvent. After taking off the product the resulting mixture may be recycled into the reactor for the next reaction cycle. Upon build-up of tars in the reaction process, the invention includes the separation of catalyst from the tars and the recycle thereof.Type: GrantFiled: December 28, 1994Date of Patent: March 26, 1996Assignee: DowElancoInventors: Mark W. Zettler, Richard E. Tobey, Ronald B. Leng
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Patent number: 5478963Abstract: The present invention describes the novel intermediates 2,3-difluoro-6-nitrobenzonitrile and 2-chloro-5,6-difluorobenzonitrile, a process for their preparation and their advantageous use for the preparation of 2,3,6-trifluorobenzoic acid, which in turn is a valuable intermediate for the preparation of insecticides and antibacterial agents. The intermediates according to the invention are prepared from 2,3,4-trifluoronitrobenzene by fluorine/cyanide exchange and subsequent denitrating chlorination. 2,3,6-Trifluorobenzoic acid can be prepared from the novel intermediates, in a manner known per se in the literature, by simple chlorine/fluorine exchange and subsequent hydrolysis in a process which overall is industrially advantageous and economically favorable.Type: GrantFiled: January 21, 1994Date of Patent: December 26, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5473095Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which R.sup.1 is --CN, --COOH, --COOR', R' being an organic radical having 1 to 6 carbon atoms, --CONH.sub.2, --COCl or --CHO and R.sup.2 is H or Cl, which comprises reacting a compound of the formula ##STR2## in which R.sup.1 is as defined above and R.sup.3 is H or Cl, with a chlorinating agent in the presence of a chlorination catalyst at -10.degree. to 200.degree. C.Type: GrantFiled: January 27, 1994Date of Patent: December 5, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
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Patent number: 5468421Abstract: A liquid crystalline compound which has a low viscosity and is electrically and chemically stable and compatible with other known liquid crystalline compounds at low temperatures, and a liquid crystal composition containing the same, which compound is a phenyl-4-cyclohexylbutylcyclohexane derivative expressed by the formula: ##STR1## wherein R represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms, and X.sub.1, X.sub.2 and X.sub.3 are each independent and X.sub.1 and X.sub.3 each represent a hydrogen atom or a halogen atom and X.sub.2 represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms (wherein one --CH.sub.2 CH.sub.2 -- bond may be replaced by a --CH.dbd.CH-- bond and one non-adjacent --CH.sub.2 -- bond may be replaced by an oxygen atom), a halogen atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group.Type: GrantFiled: April 28, 1993Date of Patent: November 21, 1995Assignee: Chisso CorporationInventors: Shuichi Matsui, Yasuyuki Goto, Yuichi Onji, Atsuko Fujita
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Patent number: 5466859Abstract: Fluorobenzonitriles and chlorofluorobenzonitriles are prepared in an advantageous manner from the corresponding chlorobenzonitriles and an alkali metal fluoride in a chlorine-fluorine exchange reaction, by catalyzing the reaction with a quaternary ammonium compound comprising at least one alkoxypolyoxyalkyl radical.Type: GrantFiled: July 19, 1994Date of Patent: November 14, 1995Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs, Ralf Pfirmann
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Patent number: 5449810Abstract: A novel liquid crystal material having a carbon chain containing a conjugated diene as a terminal substituent of the molecule and exhibiting superior characteristics is provided, which is a diene derivative expressed by the formula (I) ##STR1## wherein R and R' each independently represent 1-5C alkyl; A and B each independently represent 1,4-cyclohexylene or 1,4-phenylene; n is 0 or 1; m is an integer of 0 to 2; X and X' each independently represent H atom or F atom when A is 1,4-phenylene or represent H atom when A is 1,4-cyclohexylene; Y is alkyl, halogen or CN, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-phenylene, or represent alkyl, alkoxy, methyl group substituted by 1-3 halogen atoms or trihaloalkoxy when A is 1,4-cyclohexylene; and R and R' are not simultaneously alkyl chain of 4 or more carbon atoms.Type: GrantFiled: April 1, 1993Date of Patent: September 12, 1995Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5401434Abstract: A novel liquid crystal compound having an intermediate group of a cis-1,4-substituted 2-butenyl group, low viscosity and a broad mesomorphic temperature range is provided, which compound is expressed by the following formula: ##STR1## wherein R.sup.1 represents an alkyl group of 1 to 10 carbon atoms, n represents 1 or 2, X represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group, an alkoxy group, a methyl group substituted by 1 to 3 halogen atom(s) or a trihaloalkoxy group, and Y and Y' each independently represents a hydrogen atom, or a halogen atom.Type: GrantFiled: April 1, 1993Date of Patent: March 28, 1995Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Yuichi Onji, Makoto Ushioda, Yasuyuki Goto
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Patent number: 5370822Abstract: A novel liquid crystal compound exhibiting a low driving voltage, a liquid crystal phase within a broad temperature range and a good compatibility with other known liquid crystal compounds at low temperatures is provided, which compound is expressed by the formula ##STR1## wherein R is H or a linear or branched alkyl group of 1-10C, X is H or F, and the vinyl group has a transconfiguration. This compound has a high dielectric anisotropy value for its relatively low viscosity and can drive liquid crystal display elements under a low voltage, and further exhibits a liquid crystal phase within a broad temperature range of about room temperature to about 200.degree. C., and exhibits a good compatibility with many other liquid crystalline compounds such as ester compounds, Schiff's base compounds, biphenyls, phenylcyclohexanes, heterocyclic compounds, fluorine compounds, etc., particularly a good compatibility at low temperatures, and hence can provide improved liquid crystal materials.Type: GrantFiled: September 10, 1993Date of Patent: December 6, 1994Assignee: Chisso CorporationInventors: Shuichi Matsui, Yuichi Onji, Atsuko Fujita, Tomoyuki Kondo, Yasuyuki Goto
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Patent number: 5356558Abstract: A tolane derivative, a liquid crystal composition containing the derivative, and a liquid crystal display device including the composition, in which the tolane derivative is represented by the following general formula: ##STR1## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms, and each of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 represents a fluorine atom or a hydrogen atom wherein at least one X represents a fluorine atom, and Y represents a nitrile group or a straight-chain alkyl group having 1 to 10 carbon atoms.By blending the above-described compound with a general liquid crystal composition, a liquid crystal composition is provided which exhibits a wide practical temperature range as well as a large anisotropy of refractive index.Type: GrantFiled: July 21, 1993Date of Patent: October 18, 1994Assignee: Seiko Epson CorporationInventors: Shuhei Yamada, Shuji Ikukawa, Jun Ito, Jitsuko Nakayama
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Patent number: 5321046Abstract: Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.Type: GrantFiled: October 27, 1992Date of Patent: June 14, 1994Assignee: Bristol-Myers Squibb CompanyInventors: Sing-Yuen Sit, John J. Wright, Jeff A. Field
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Patent number: 5312958Abstract: A process for the production of a compound of general formula ##STR1## wherein R represents cyano, carboxy which may be esterified or amidated or tetrazolyl which may be substituted, comprising brominating the corresponding methyl compound with a brominating agent such as N -bromoacetamide, N-bromophtalimide, N-bromosuccinimide and so on in a halogenated hydrocarbon solvent in the presence of an azobis compound.Type: GrantFiled: January 26, 1993Date of Patent: May 17, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Syuji Suenaga, Hitoshi Kawaguchi, Takeshi Kato
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Patent number: RE36849Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.Type: GrantFiled: April 1, 1993Date of Patent: September 5, 2000Assignee: Merck Patent GmbHInventors: Hans P. Schad, Stephen M. Kelly, Eike Poetsch, Reinhard Hittich, Georg Weber