Nitrogen Containing Material Utilized Patents (Class 568/436)
  • Patent number: 5162577
    Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: November 10, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Raffaello Masciadri
  • Patent number: 5155280
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10.degree. C. to about 20.degree. C. and thereafter separating out the aldehyde.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5155279
    Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a solvent, in the absence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the aldehyde.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: October 13, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: 5155277
    Abstract: A process for converting tertiary amine N-oxides to aldehydes by reacting tertiary amine N-oxides in the presence of a catalytic quantity of a vanadium containing compound.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: October 13, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Serge Henrot, Claude Mercier
  • Patent number: 5149882
    Abstract: 2-chloro-5-nitrobenzaldehyde or an acetal thereof is isolated from a mixture of isomers thereof at a temperature of from -10.degree. to +140.degree. C., by suspending the mixture of isomers in a solvent or solvent mixture.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: September 22, 1992
    Inventors: Bernd Schaefer, Wolfgang Freund, Gernot Reissenweber
  • Patent number: 5124487
    Abstract: p-Trifluoromethyl benzaldehydes are prepared by the catalytic reduction reaction of p-trifluoromethyl benzonitriles with hydrogen in an aqueous formic acid media in the presence of a nickel/aluminum alloy catalyst.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: June 23, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: James J. Maul, Garra C. Lester, Henry C. Lin
  • Patent number: 5082976
    Abstract: Benzaldehydes of the formula ##STR1## can be obtained by reaction of substituted .beta.-amino-styrenes of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.10, m, n and o have the scope of meaning indicated in the description, with oxygen in the presence of a Cu compound in the solution of an aprotic polar solvent at 0.degree.-120.degree. C.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: January 21, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Helmut Kraus
  • Patent number: 4845305
    Abstract: This invention presents a method for the preparation of isophthalaldehyde in an all-aqueous solution using m-xylenediamine, hexamethylenetetramine, and HCl as the only reactants. Such a process permits the preparation of high yield of a high purity product.
    Type: Grant
    Filed: July 7, 1988
    Date of Patent: July 4, 1989
    Assignee: National Starch and Chemical Corporation
    Inventor: Eric A. Meier
  • Patent number: 4766251
    Abstract: A multi-step process for the preparation of ethynylbenzaldehydes from bromo- or iodobenzaldehydes is disclosed. The arylhalogen is replaced with a protected ethynyl compound which is subsequently cleaved by base to form the arylacetylene. The aldehydic functionality is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 23, 1988
    Assignee: National Starch and Chemical Corporation
    Inventors: Robert D. Rossi, Steven P. Fenelli
  • Patent number: 4647446
    Abstract: A method for detecting the blood flow in animals, particularly in the brain, is provided wherein a detectable amount of a novel radioactive compound of the formula I is administered to one animal: ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl of 1 to 6 carbon atoms or benzyl;R.sub.3 is alkyl of 1 to 6 carbon atoms, benzyl, cyclopropylalkyl of 4 to 6 carbon atoms, or cyanoalkyl of 2 to 6 carbon atoms;R.sub.4 is hydrogen, benzyl or alkyl of 1 to 6 carbon atoms;with the provisos that R.sub.4 is not isopropyl and when R.sub.4 is methyl, R.sub.3 is not benzyl;and X is a radioactive halogen.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: March 3, 1987
    Assignee: The Regents of the University of California
    Inventors: Thornton W. Sargent, III, Alexander T. Shulgin, Chester A. Mathis
  • Patent number: 4645852
    Abstract: In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: February 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Richard C. Krauss
  • Patent number: 4590281
    Abstract: Provided is a process for preparing an aldehyde or aldehydes represented by the following formula (III), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted with an unsaturated alcohol represented by the following formula (II) in a solvent containing a base in the presence of a transition metal catalyst at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ] X.sup..crclbar. (I)CHR.sub.1 .dbd.CR.sub.2 --CH.sub.2 OH (II)Ar.sub.3 --CHR.sub.1 --CHR.sub.2 --CHO (III)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups, X.sup..crclbar. is a counter ion which is inert to the above reaction, Ar.sub.3 is the same aryl group as Ar.sub.1 or Ar.sub.2, and R.sub.1 and R.sub.2 are each hydrogen atom or an alkyl group of C.sub.1 to C.sub.12.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: May 20, 1986
    Assignee: Nippon Petrochemicals Company
    Inventors: Yasuo Yamazaki, Takehiko Suzuki
  • Patent number: 4588844
    Abstract: Aromatic aldehydes are prepared by formylating the corresponding aromatic compounds with urotropine in the presence of hydrogen fluoride. By the described process certain new aromatic aldehydes can be prepared.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: May 13, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst Kysela, Erich Klauke
  • Patent number: 4584410
    Abstract: In a Reimer-Tiemann reaction for the preparation of a mixture of two hydroxybenzaldehydes (i.e., salicylaldehyde and p-hydroxybenzaldehyde) by reacting phenol with chloroform and an aqueous alkali solution in a heterogeneous system, the two hydroxybenzaldehydes can be prepared in a controlled formation ratio, yield and reaction rate depending upon the conditions used when the reaction is carried out in the presence of a phase transfer catalyst selected from the group consisting of a cationic type phase transfer catalyst, an amphoteric type phase transfer catalyst and an anionic type phase transfer catalyst.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: April 22, 1986
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Kazuhiko Hamada, Gohfu Suzukamo, Fujio Masuko, Makoto Nakamura
  • Patent number: 4578462
    Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.
    Type: Grant
    Filed: August 22, 1983
    Date of Patent: March 25, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
  • Patent number: 4568772
    Abstract: This invention discloses a novel process for producing p-t-butyl-.alpha.-methyldihydrocinnamaldehyde which comprises converting the .alpha.-methyldihydrocinnamaldehyde to an enamine, oxazolidine or a Schiff's base, reacting said derivative with a tertiary butyl cation, and then removing the protective group.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: February 4, 1986
    Assignee: Givaudan Corporation
    Inventors: Albert Gabbai, Karl-Fred De Polo
  • Patent number: 4558163
    Abstract: This disclosure describes a novel process for the preparation of 9,10-anthracenedicarboxaldehyde by the oxidation of 9,10-bis(chloromethyl)anthracene.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: December 10, 1985
    Assignee: American Cyanamid Company
    Inventor: Steven L. Peake
  • Patent number: 4540826
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Jim D. Byers
  • Patent number: 4500721
    Abstract: A process for producing benzaldehydes by catalytic reduction of benzonitriles in the presence of an acid using a Raney nickel catalyst pretreated with a copper salt is disclosed.
    Type: Grant
    Filed: February 23, 1983
    Date of Patent: February 19, 1985
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Hiroshi Yamachika, Hirotoshi Nakanishi
  • Patent number: 4465865
    Abstract: A method of preparing terephthalic aldehyde or isophthalic aldehyde from p-xylene or m-xylene, which comprises chlorinating the side chain or p or m xylene to a chlorination degree of 2.5 to 3.5, and thereafter contacting the so-chlorinated product with hexamethylenetetramine in aqueous solution at elevated temperature whereby the corresponding aldehyde is obtained.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: August 14, 1984
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Fritz Englander, Klaus-Dieter Steffen
  • Patent number: 4426534
    Abstract: 2,2'-bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: January 17, 1984
    Assignee: Thiokol Corporation
    Inventor: Frank S. Guziec, Jr.
  • Patent number: 4424389
    Abstract: A process for producing chroman, a compound of the formula, ##STR1## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, which comprises reacting a compound of the formula, ##STR2## or an optically active compound thereof wherein A is an aryl group and R.sub.5 is a C.sub.1 -C.sub.4 alkyl group, with a compound of the formula, ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.3 alkyl group, X is a halogen atom and R.sub.2, R.sub.3 and R.sub.4 are as defined above, to obtain a compound of the formula, ##STR4## or an optically active compound thereof wherein A, R.sub.1, R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: January 3, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yoji Sakito
  • Patent number: 4408077
    Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.
    Type: Grant
    Filed: November 13, 1981
    Date of Patent: October 4, 1983
    Assignee: Ayerst, McKeena & Harrison, Inc.
    Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
  • Patent number: 4383949
    Abstract: A process for the preparation of a 3-bromo-4-fluorobenzaldehyde acetal of the formula ##STR1## in which R.sup.1 is methyl or ethyl,which comprises reacting a 3-bromo-4-fluoro-benzoic acid halide with ammonia to form 3-bromo-4-fluoro-benzoic acid amide, dehydrating said amide to form 3-bromo-4-fluoro-benzonitrile, reacting the nitrile with formic acid in the presence of a catalyst at a temperature between about 0.degree. and 150.degree. C. to form 3-bromo-4-fluorobenzaldehyde, and reacting said aldehyde with R.sup.1 OH or a derivative thereof capable of forming an acetal. The amide and nitrile are new compounds. The acetals are known intermediates in the synthesis of pyrethroid-like insecticides.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: May 17, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Hans-Jochem Riebel, Uwe Priesnitz, Erich Klauke
  • Patent number: 4383122
    Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: May 10, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4337346
    Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 29, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
  • Patent number: 4335052
    Abstract: A process for the preparation of Benzaldehydes substituted in the nucleus is disclosed by oxidation of the corresponding benzyl halides. The process is performed in the presence of water using aminoxides of tertiary amines.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: June 15, 1982
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Gunther Bernhardt, Egon-Norbert Petersen, Gerhard Daum
  • Patent number: 4328374
    Abstract: A process for the production of aromatic dialdehydes which comprises reacting xylene chloride selected from the group consisting of .alpha.,.alpha.,.alpha.'-trichloroxylene alone, or a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.'-dichloroxylene, a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene and a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene, .alpha.,.alpha.'-dichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene with nitric acid.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: May 4, 1982
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Shigeo Yoshinaka, Masaharu Doya
  • Patent number: 4322563
    Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: March 30, 1982
    Assignee: Merck & Co., Inc.
    Inventor: William F. Hoffman
  • Patent number: 4321412
    Abstract: In a process for the preparation of aromatic monoaldehydes by reacting monochlorinated methylaromatics with hexamethylenetetramine by a Sommelet reaction, the improvement that in place of pure chloromethylaromatics the chlorination mixtures produced by photochlorination of the methylaromatics are employed and are treated with hexamethylenetetramine without prior working up, after which the Sommelet reaction is allowed to take place.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: March 23, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Schoch, Michael Kroener, Rudi Widder
  • Patent number: 4287368
    Abstract: A new radioenzymatic assay for catecholamines utilizing the catechol-0-methyl transferase transfer of a methyl group from a labeled methyl donor to the catecholamines followed by isolation of the 0-methylated(.sup.3 H)catecholamine and the subsequent measurement of radioactivity.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: September 1, 1981
    Assignee: The Upjohn Company
    Inventors: Garland A. Johnson, Jacob D. Peuler
  • Patent number: 4206152
    Abstract: The present invention provides a process for the production of unsubstituted or substituted o-phthalaldehydes by hydrolysis of .alpha.,.alpha., .alpha.',.alpha.'-tetrahalogeno-o-xylenes with a carboxylate in an aqueous medium in the presence of a phase transfer catalyst and an organic base.
    Type: Grant
    Filed: December 21, 1978
    Date of Patent: June 3, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Jacques Gosteli