Halogen Containing Patents (Class 568/56)
  • Patent number: 10450253
    Abstract: A simple production process is provided of a perfluoroalkyl compound that uses monohydroperfluoroalkane as a starting material, the perfluoroalkyl compound being an important intermediate of organic electronic materials, medicine, agricultural chemicals, functional polymer materials and the like. With monohydroperfluoroalkane is reacted a base and then a carbonyl compound to produce an alcohol having a perfluoroalkyl group. For example, potassium hydroxide is made to interact with trifluoromethane, and a reaction with a carbonyl compound is induced to produce an alcohol having a trifluoromethyl group.
    Type: Grant
    Filed: February 16, 2017
    Date of Patent: October 22, 2019
    Assignees: KANTO DENKA KOGYO CO., LTD., NATIONAL UNIVERSITY CORPORATION GUNMA UNIVERSITY
    Inventors: Hideki Amii, Kazuki Komoda, Masafumi Kobayashi, Yutaka Nakamura, Ryusuke Obinata, Akinori Harada
  • Patent number: 9598340
    Abstract: The coupling of aryl, heteroaryl, and vinyl halides with ?,?-difluoroketones or silyl ethers or siylenol ethers of ?,?-difluoroketones and ?,?-difluoroamides and esters are described. Further derivatization of the coupling products (such as ketone cleavage and Baeyer-Villiger oxidation) is also described.
    Type: Grant
    Filed: April 7, 2014
    Date of Patent: March 21, 2017
    Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: John F. Hartwig, Shaozhong Ge, Wojciech Chaładaj
  • Patent number: 9068047
    Abstract: Disclosed is a process for producing poly(arylene sulfide) which includes: a polymerization step of polymerizing a dihalogenated aromatic compound and at least one sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrogen sulfides in an organic amide solvent, preferably in the presence of a phase separating agent; a separation step of separating a polymer from a reaction liquid containing a produced polymer after the polymerization step; a washing step of washing the polymer with a washing liquid that consists of water and/or an organic solvent; and a separated liquid treatment step of bringing both a separated liquid that has been recovered after the separation of the polymer in the separation step and a separated liquid containing a wash waste liquid that has been recovered after the separation of the polymer in the washing step into contact with an alkaline compound. Also disclosed is poly(arylene sulfide).
    Type: Grant
    Filed: April 21, 2011
    Date of Patent: June 30, 2015
    Assignee: KUREHA CORPORATION
    Inventors: Yoshihiro Ichinose, Masanori Kobayashi, Tomoyoshi Koizumi, Mitsuhiro Matsuzaki
  • Publication number: 20150132223
    Abstract: One aspect of the present invention relates to a method of preparing radiofluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammnonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.
    Type: Application
    Filed: November 25, 2014
    Publication date: May 14, 2015
    Inventors: David R. Elmaleh, Alan J. Fischman, Timothy M. Shoup
  • Publication number: 20150069297
    Abstract: A liquid crystal compound having high stability to heat and light, etc., a high clearing point, a low minimum temperature of liquid crystal phase, a low viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant, and good compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound, and a LCD element using the composition are described. The compound is represented by formula (1): wherein, for example, R1 is C1-10 alkyl, ring A1, ring A2, ring A3, ring A4 and ring B1 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted with halogen, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5-diyl, Z1, Z2, Z3 and Z4 are single bonds, l, m, n and o are independently 0 or 1, and l+m+n+o?1.
    Type: Application
    Filed: February 7, 2013
    Publication date: March 12, 2015
    Inventor: Hiroyuki Tanaka
  • Publication number: 20140243404
    Abstract: This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed.
    Type: Application
    Filed: September 13, 2011
    Publication date: August 28, 2014
    Applicant: The Trustees of Columbia University in the City of New York
    Inventors: Scott Alan Snyder, Daniel S. Treitler, Alexandria P. Brucks, Andreas Gollner, Maria I. Chiriac, Nathan E. Wright, Jason J. Pflueger, Steven P. Breazzano
  • Publication number: 20140235898
    Abstract: Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds. Finally, various intermediate compounds for use in preparing substituted phenylsulfur trifluorides are provided.
    Type: Application
    Filed: March 14, 2014
    Publication date: August 21, 2014
    Applicant: UBE INDUSTRIES, LTD.
    Inventor: Teruo UMEMOTO
  • Publication number: 20140128560
    Abstract: Described herein is a trifluorostyrene compound that can be used as a monomer to form crosslinkable polymers, and their use as polymer electrolyte membranes.
    Type: Application
    Filed: January 10, 2014
    Publication date: May 8, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark Gerrit Roelofs, MARK F. TEASLEY
  • Patent number: 8703969
    Abstract: A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R1, R2, R3, and R4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X? represents an anion.
    Type: Grant
    Filed: July 13, 2010
    Date of Patent: April 22, 2014
    Assignees: Nagoya Institute of Technology, Tosoh F-Tech, Inc.
    Inventors: Norio Shibata, Takumi Kagawa
  • Publication number: 20130115168
    Abstract: One aspect of the present invention relates to a method of preparing radiofluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.
    Type: Application
    Filed: September 4, 2012
    Publication date: May 9, 2013
    Applicant: The General Hospital Corporation
    Inventors: David R. Elmaleh, Alan J. Fischman, Timothy M. Shoup
  • Patent number: 8263693
    Abstract: The present invention provides a flame retardant resin composition comprising (A) 100 weight part of a basic resin comprising acrylonitrile-butadiene-styrene copolymer resin and styrene-acrylonitrile copolymer resin; and (B) 10-30 weight part of a bromine-based organic compound flame retardant, and selectively comprising (C) 1-20 weight part of an antimony-based auxiliary flame retardant and (D) 1-10 weight part of one or more compounds selected from the group consisting of metalstearate and stearamide compounds, wherein the bromine-based organic compound flame retardant (B) is octabromodiphenyl ethane. The flame retardant resin composition of the present invention has excellent flame retardancy, impact strength and melt flow index.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: September 11, 2012
    Assignee: LG Chem, Ltd.
    Inventors: You-seok Seo, Ki-young Nam, Yong-yeon Hwang, Je-sun Yoo, Hyeon-gook Kim, Myeong-soo Song
  • Patent number: 8246859
    Abstract: The invention describes a process for reducing the surface energy of organic materials such as for example increasing the oil and water repellency and stain release of organic materials, which comprises treating the organic material with at least a compound of the formula I wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is —CH(R11)—S(O)p—R12; R11 is hydrogen, C1-C8alkyl, unsubstituted or with C1-C4alkyl substituted phenyl; R12 is a monovalent perfluorinated alkyl or alkenyl, linear or branched organic radical having four to twenty fully fluorinated carbon atoms, and p is 0, 1 or 2.
    Type: Grant
    Filed: June 4, 2007
    Date of Patent: August 21, 2012
    Assignee: BASF SE
    Inventors: Michèle Gerster, Manuel Mihalic
  • Publication number: 20120172615
    Abstract: A substituted alkenylbenzene compound of formula (4): wherein X1 is a halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl; X3 is a hydrogen, halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6alkylthio; X4 is a hydrogen, halogen, cyano, C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy; R3 is —C(R3a)(R3b)R3c, where R3a and R3b are a halogen, or R3a and R3b together form a 3- to 6-membered ring together with the carbon bonding them by forming a C2-C5haloalkylene chain, and R3c is a hydrogen, halogen, C1-C5alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio, with a proviso that where X1 is a fluorine, chlorine or trifluoromethyl, and X2 and X3 are hydrogen, where X1 and X2 are fluorine and X3 is a hydrogen, or where X1 and X2 are trifluoromethyl and X3 is a hydrogen, R3c is a hydrogen, chlorine, bromine, iodine,
    Type: Application
    Filed: January 13, 2012
    Publication date: July 5, 2012
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Takeshi MITA, Takamasa KIKUCHI, Takashi MIZUKOSHI, Manabu YAOSAKA, Mitsuaki KOMODA
  • Publication number: 20120130090
    Abstract: A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R1, R2, R3, and R4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X? represents an anion.
    Type: Application
    Filed: July 13, 2010
    Publication date: May 24, 2012
    Inventors: Norio Shibata, Takumi Kagawa
  • Publication number: 20110251432
    Abstract: The invention relates to new processes for preparation of 18F-labelled alkylation reagents that can be used in the alkylation of amines that are suitable for use in labelling of Positron Emission Tomography (PET) radiotracers.
    Type: Application
    Filed: August 27, 2008
    Publication date: October 13, 2011
    Inventors: Bengt Langstrom, Tor Kihlberg
  • Patent number: 7951602
    Abstract: Mass defect labeled peptides and methods of identifying peptides are provided. In particular, embodiments of the present disclosure include mass defect labels for polypeptides that include at least one cysteine and/or at least one tryptophan and methods of using the mass defect labels to identify polypeptides. One embodiment, among others, includes a mass defect labeled peptide including at least one cysteine residue labeled with 2,4-dibromo-acetanilide. Another embodiment, among others, includes a mass defect labeled peptide including at least one tryptophan residue labeled with 4,6-dibromo-2-trifluoromethylphenylsulfenyl chloride.
    Type: Grant
    Filed: August 28, 2007
    Date of Patent: May 31, 2011
    Assignee: University of Georgia Research Foundation, Inc.
    Inventors: I. Jonathan Amster, Robert S. Phillips
  • Publication number: 20110046247
    Abstract: Described herein is a trifluorostyrene compound that can be used as a monomer to form crosslinkable polymers.
    Type: Application
    Filed: December 18, 2008
    Publication date: February 24, 2011
    Applicant: E.I. Du Pont De Nemours and Company
    Inventors: Mark Gerrit Roelofs, Mark F. Teasley
  • Publication number: 20110028725
    Abstract: The present disclosure provides methods of synthesizing alkylating agents and methods of use.
    Type: Application
    Filed: August 17, 2010
    Publication date: February 3, 2011
    Applicant: The Queen's Medical Center
    Inventor: John L. Lim
  • Publication number: 20100234605
    Abstract: New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.
    Type: Application
    Filed: December 9, 2008
    Publication date: September 16, 2010
    Applicant: IM&T RESEARCH, INC.
    Inventors: Teruo Umemoto, Rajendra P. Singh
  • Publication number: 20100137608
    Abstract: Methods for carbon-sulfur (C—S) or carbon-oxygen (C—O) coupling reactions are provided. The methods involve the use of a transition metal complex comprising a heterocyclic carbene ligand complexed with a transition metal. Transition metal complexes comprising a heterocyclic carbene ligand complexed with nickel are also provided. The nickel heterocylic carbene complexes may be used for C—S or C—O coupling reactions.
    Type: Application
    Filed: May 2, 2008
    Publication date: June 3, 2010
    Inventor: Yugen Zhang
  • Patent number: 7709548
    Abstract: A monosulfonium salt in which very little unreacted raw material remains, which has a purity of at least 96%, and which has one sulfonio group in its molecule is manufactured without a refining step. After (a) an aryl compound, (b) a sulfoxide compound, (c) a dehydrating agent, and (d) a BF4, PF6, AsF6, or SbF6 salt of an alkali metal or an alkaline earth metal are introduced into a reaction system, (e) an inorganic acid is added, so that the aryl compound (a) and the sulfoxide compound (b) are subjected to dehydration condensation.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: May 4, 2010
    Assignee: San-Apro Limited
    Inventors: Masashi Date, Hideki Kimura, Shinji Yamashita, Jiro Yamamoto
  • Patent number: 7659317
    Abstract: Methods and reagents for labeling synthesis of organohalides by transition metal mediated carbonylation reactions using carbon-isotope labeled carbon monoxide are provided. The resultant carbon-isotope labeled organohalides are useful as radiopharmaceuticals, especially for use as precursors in Positron Emission Tomography (PET). Associated PET tracers and kits for PET studies are also provided.
    Type: Grant
    Filed: March 10, 2005
    Date of Patent: February 9, 2010
    Assignee: GE Healthcare Limited
    Inventors: Jonas Eriksson, Bengt Langstrom, Gunnar Antoni
  • Publication number: 20080262238
    Abstract: A dendron or dendrimer, which has, as a recurring unit of each branch, a structure of formula (I): wherein TC designates a linkage to a former generation in the direction to a focal point of the dendron or a core of the dendrimer; TT designates a linkage to a next generation in the direction to a terminal; X is a divalent group comprised of at least one heteroatom; L1 and L2 each are a divalent linking group; R is a hydrogen atom or a substituent; and a method of producing a dendron or a dendrimer; and a method of producing a thioacetal compound.
    Type: Application
    Filed: March 28, 2005
    Publication date: October 23, 2008
    Inventor: Koki Nakamura
  • Publication number: 20080255370
    Abstract: The chemistry of [13C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.
    Type: Application
    Filed: April 4, 2008
    Publication date: October 16, 2008
    Inventor: Rodolfo A. Martinez
  • Patent number: 7339081
    Abstract: A process for preparing bromo-1-oxypentafluorosulfanylbenzene is provided, the process including the step of brominating pentafluorosulfanyloxybenzene with a bromination agent to provide the bromo-1-oxypentafluorosulfanylbenzene. The process is more effective than prior art processes for preparing such compounds.
    Type: Grant
    Filed: July 10, 2006
    Date of Patent: March 4, 2008
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert George Syvret, Gauri Sankar Lal
  • Patent number: 7323602
    Abstract: A process for preparing an intermediate compound of formula (II) where n is an integer of from 3 to 14; R1 is haloC1-10alkyl, C1-10alkyl, C2-10alkenyl, C2-10cycloalkyl, carboxyC1-10alkyl, C1-10alkoxycarbonylC1-10alkyl, aryl (such as phenyl), aryl(C1-10)alkyl (such as phenyl(C1-10)alkyl) or di(C1-6alkyl)amino; and R2 is a halo group; the process comprising halogenation of a compound of formula (III) where n and R1 are as defined above. Novel compounds are also described and claimed.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: January 29, 2008
    Assignee: AstraZeneca AB
    Inventors: Kenneth Edwin Herbert Warren, Anne Margaret Lamont Kane
  • Patent number: 7087789
    Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“?CF2?”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.
    Type: Grant
    Filed: January 12, 2004
    Date of Patent: August 8, 2006
    Assignee: University of Southern California
    Inventors: G. K. Surya Prakash, Jinbo Hu, George A. Olah
  • Patent number: 7087764
    Abstract: A process for producing a compound of the formula (II): wherein Hal1 represents halogen and R1 and R2 each independently represents halogen, alkyl, alkoxy, nitro or cyano, which comprises allowing a halogenating agent to react with a compound of the formula (I): wherein Alk represents branched alkyl and R1 and R2 are as defined above.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: August 8, 2006
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsutomu Aoki, Toshiro Konoike
  • Publication number: 20040230079
    Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“−CF2−”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.
    Type: Application
    Filed: January 12, 2004
    Publication date: November 18, 2004
    Inventors: G.K.Surya Prakash, Jinbo Hu, George A. Olah
  • Patent number: 6770776
    Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: August 3, 2004
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Janin, Laurent Saint-Jalmes
  • Publication number: 20030187233
    Abstract: Perfluoroisopropylbenzene derivatives of the general formula (I) or salts thereof, useful as intermediates or raw materials in the synthesis of various industrial materials including agricultural chemicals, drugs and surfactants, wherein X1 is H, halogeno, formyl, optionally halogenated C1-6 alkyl, —C(═O)—R1 (wherein R1 is H, halogeno, hydroxyl, C1-6 alkyl, or NR2R3, with R2 and R3 being each H, C1-6 alkyl, or the like), or the like; X3 is H, halogeno, hydroxyl, cyano, isocyanato, hydrazino, diazo, —C(═O)—R1, —SO2—R4 (wherein R4 is halogeno, hydroxyl, C1-6 alkyl, or NR5R6, with R5 and R6 being each H or C1-6 alkyl), or the like; and X4 is H, halogeno, C1-6 alkyl, or C1-6 alkoxy, with publicly known compounds being excepted.
    Type: Application
    Filed: September 11, 2002
    Publication date: October 2, 2003
    Inventors: Masanobu Onishi, Kenichi Ikeda, Takashi Shimaoka, Masanori Yoshida
  • Publication number: 20030166971
    Abstract: It is an object of the present invention to provide a process for producing highly pure 4-bromothioanisole, which is useful in the manufacture of medicinal chemicals, agrochemicals or functional materials, in a simple and industrially advantageous manner.
    Type: Application
    Filed: March 25, 2003
    Publication date: September 4, 2003
    Inventors: Kenichi Wakimura, Hitoshi Karino, Hirokazu Kagano
  • Patent number: 6596905
    Abstract: The invention concerns a method for preparing aromatic diphenyl thioethers. More particularly the invention concerns the preparation of 4-chloro-4′-thiomethyldiphenylether. The inventive method for preparing an aromatic diphenyl thioether is characterised in that it consists in reacting in an aqueous medium a diazonium salt of an aromatic diphenyl compound with a disulphide sulphur compound, in the presence of an efficient amount of a coupling catalyst.
    Type: Grant
    Filed: August 27, 2001
    Date of Patent: July 22, 2003
    Assignee: Rhodia Chimie
    Inventors: Thierry Schlama, Jean-Christophe Bigouraux
  • Publication number: 20030100785
    Abstract: The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.
    Type: Application
    Filed: August 30, 2002
    Publication date: May 29, 2003
    Inventors: Sangho Koo, Minkoo Ji
  • Publication number: 20030073847
    Abstract: The dihalopropene compounds of the general formula (I) have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
    Type: Application
    Filed: March 4, 2002
    Publication date: April 17, 2003
    Applicant: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 6518460
    Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O)—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.
    Type: Grant
    Filed: May 8, 2002
    Date of Patent: February 11, 2003
    Assignee: Syntex (U.S.A.) LLC
    Inventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
  • Patent number: 6506286
    Abstract: A reagent comprising a compound of formula (I): Rf—M(X)(Z)n—Y—R, wherein R is a hydrocarbon radical advantageously having at most 10 carbon atoms and being selected from alkyls and aryls; Rf is a radical of formula II: R1—(C&Xgr;2)m—CF2—, where R1 is a fluorine or chlorine atom or a carbon radical, m is 0 or a integer from 0-12, and each &Xgr;, which may be the same or different, is a chlorine or preferably fluorine atom, with the proviso that when m is 0, R1 is electroattractive, preferably a fluorine atom; n is 0 or 1; M is a non-metal selected from carbon and chalcogens with an atomic number than oxygen; and each of X, Y and Z, which are the same or different, is a chalcogen; as well as a generator, for consecutive or simultaneous addition. The reagent is useful for organic synthesis.
    Type: Grant
    Filed: August 24, 2000
    Date of Patent: January 14, 2003
    Assignee: Rhodia Chimie
    Inventors: Bernard Langlois, Nicolas Roques, Claude Wakselman, Marc Tordeux, Gérard Forat
  • Patent number: 6420573
    Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O)—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: July 16, 2002
    Assignee: Syntex (U.S.A.) LLP
    Inventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
  • Publication number: 20020052530
    Abstract: Indane dimer compounds of general formula 5, 6 or 9 and their pharmaceutical use, particularly to achieve smooth muscle relaxing activity and/or mast cell stabilizing activity and/or antiinflammatory activity are described, wherein in formulae 5 and 9, R1 and R3 to R15, and in formula 6, R1, R2 and R4 to R15, are selected from one or more of the same or different of: H, halo, hydroxy, alkoxy, aryloxy, acetoxy, carboxy, alkyl carbonyl, hydro carbonyl, amino, amido, alkylamino, hydroxylamino, amine oxide groups, azo groups, cyano, hydrazino groups, hydrazide groups, hydrazone groups, imide groups, iminoether groups, ureyl groups, oximc, nitro, nitrate, nitrite, nitroso groups, nitrile, heterocyclic groups containing one or more heteroatoms selected from N, O or S, aralkyl groups, mono and polybenzoid aryl groups, substituted aryl groups, thiol, thioureyl, phenylthiol groups, sulphonic acid groups, sulphoxide groups, sulphone groups, alkyl containing 1 to 10 carbon atoms or cycloalkyl groups containing 3 to 8 ca
    Type: Application
    Filed: June 8, 1998
    Publication date: May 2, 2002
    Inventors: JOHN WALSH, NEIL FRANKISH, HELEN SHERIDAN, WILLIAM BYRNE
  • Patent number: 6379590
    Abstract: A new method for producing unsymmetrically substituted fluorenyl compounds, one step of which is the preparation of 2,7-disubstituted fluoren-9-one derivatives via the nucleophilic substitution of a compound of the formula D wherein A′ is selected from the group consisting of —Br, —Cl, —F, —NO2, and —CN; A is selected from the group consisting of —NO2, —CN, —CO2R, —C(O)R, —SO2R, —SO2RF, —C(CN)═C(CN)2 and —CH═C(CN)2; RF is —CpF2p+1, p=from about 0 to about 10; R is an straight, branched or cyclic aliphatic alkyl group having about 1 to 10 carbon atoms, or an aromatic group such as phenyl or naphthyl; and is a carbonyl or a protected carbonyl such as a ketal or thio-ketal such as wherein R′ is —CrH2r+1; R″ is —(CH2)r—; and r is independently 2 or 3, with a nucleophilic reagent in the presence of an aprotic solvent
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: April 30, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan
  • Patent number: 6369275
    Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.
    Type: Grant
    Filed: November 17, 2000
    Date of Patent: April 9, 2002
    Assignee: Merck & Co., Inc.
    Inventors: Ian W. Davies, Michel Journet, Linda Gerena, Robert D. Larsen, Philip J. Pye, Kai Rossen
  • Publication number: 20020015826
    Abstract: Photoresist compositions, or photoacids, are used in etching circuit pathways on the surface of microelectronic components. Iodonium compounds generate a strong acid under short wavelength irradiation, which is capable of etching the polymeric surface coating of a silicon wafer. The strong acid is the conjugate acid of the counteranion. Larger counterions generate acids that diffuse to a lesser extent in the polymer resist matrix, producing better image resolution. Given the particular anion, the solubility of its diary iodonium salts will depend upon which aromatic rings are used on the iodonium molecule. A zwitterionic structure of the iodonium molecule, having both positive and negative charges on the same molecular species, can be used as photoacid composition in the photoresist step of microchip manufacturing.
    Type: Application
    Filed: April 10, 2001
    Publication date: February 7, 2002
    Inventors: Darryl Desmarteau, Vitorio Montanari, Brian H. Thomas
  • Patent number: 6342639
    Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: January 29, 2002
    Assignee: Syntex (U.S.A.) LLC
    Inventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
  • Patent number: 6326519
    Abstract: Diallylic sulfides represented by Formula I wherein: R1 and R2 are independently chosen from the group consisting of —CHO, —CH2Cl, —CH2Br, —CH2I, —CH2OH, CH2OSO2CF3, —CH2OSO2Ph, —CH2OSO2C6H4CH3 and —CH2OSO2CH3 and processes for making the same.
    Type: Grant
    Filed: June 4, 2001
    Date of Patent: December 4, 2001
    Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
  • Patent number: 6326337
    Abstract: An oxidation-corrosion additive for enhancing the stability of PFPAEs which has the formula: wherein Q is —Rf or —S—Rf, Rf is a perfluoroalkyl or perfluoroalkylether group having 1 to 30 carbon atoms, x and y are integers, each having a value of 0-5, wherein the sum of x and y is in the range of 1 to 10. In the formula above, Rf may be linear or branched. The additive can be a single component or a mixture of components varying in the number and relative positions of x and y. The additive can be used alone or with other suitable additives in PFPAE base fluids.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: December 4, 2001
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Kalathil C. Eapen, Grace J. Chen, Wayne E. Ward, Harvey L. Paige
  • Patent number: 6316636
    Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: November 13, 2001
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Janin, Laurent Saint-Jalmes
  • Patent number: 6225505
    Abstract: The present invention lies in a process for producing a trifluoromethylthiomethylbenzene derivative represented by the following general formula (2): (wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group, a nitro group, or a benzoyl group which may be substituted with halogen atom, alkyl group, alkoxy group, aliphatic or aromatic acyl group, nitro group, cyano group or alkoxycarbonyl group; n is an integer of 1 to 5; when n is an integer of 2 or more, a plurality of R's may be the same of each independently different), which process comprises reacting, in acetonitrile, a benzyl halide derivative represented by the following general formula (1): (wherein R and n have the same definitions as given above; and X is a halogen atom, an alkylsulfonyloxy group or an arylsulfonyloxy group which may be substituted with alkyl group or halogen atom) with thiophosgene and potassium fluoride.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: May 1, 2001
    Assignees: Ihara Chemical Industry Co., LTD, Kumiai Chemical Industry Co., LTD
    Inventors: Yoshikazu Kimura, Hidetaka Hiyoshi, Keiji Toriyabe, Nobuhide Wada
  • Patent number: 6175042
    Abstract: This invention relates to a process for preparing perfluoroalkyl aryl sulfides by reaction of disulfides with alkali metal salts of aliphatic perfluorocarboxylic acids in the presence of a high-boiling aprotic solvent at elevated temperature and reduced pressure, wherein the product formed is distilled off at the rate at which it is formed. This invention further relates to the novel compounds 2-nitrophenyl pentafluoroethyl sulfide and 2-aminophenyl pentafluoroethyl sulfide.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: January 16, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Vera Yakovlevna Popkova, Albrecht Marhold
  • Patent number: 6140515
    Abstract: Described is a process of preparing 3-aryl, 4-aryloxy furan-5-ones which are useful as inhibitors of cyclooxygenase-2 (COX-2). Such compounds are useful as anti-inflammatory agents. The process is directed to an asymmetric synthesis which involves: a trisubstituted styrene derivative preparation via Horner-Wadsworth-Emmons reaction and subsequent one pot trifluoromethylation of the allylic alcohol; preparation of the .alpha.-hydroxyl ketone using Sharpless asymmetric dihydroxylation and Swern oxidation; the esterification of the .alpha.-hydroxyl ketone with the phenoxy acetic acid; and the Dieckman condensation of the resulting ester.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: October 31, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Cheng Y. Chen, Lushi Tan, Robert D. Larsen
  • Patent number: 6121496
    Abstract: The present invention relates to a process for the acylation of an aromatic thioether. In its preferred variant, the invention resides in a process for the condensation of acetic anhydride or acetyl chloride with thioanisole. The process for the acylation of an aromatic thioether according to the invention is characterised in that it consists in reacting said thioether with an acylating agent chosen from the group formed by the halides of carboxylic acids and the anhydrides of carboxylic acids, in the presence of an effective quantity of an acid zeolite.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: September 19, 2000
    Assignee: Rhodia Chemie
    Inventors: Laurent Gilbert, Michel Spagnol