Process Of Alkylating The Hetero Ring Patents (Class 549/86)
  • Patent number: 9012632
    Abstract: Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.
    Type: Grant
    Filed: December 25, 2009
    Date of Patent: April 21, 2015
    Assignee: Riken
    Inventors: Masaaki Suzuki, Hisashi Doi, Hiroko Koyama
  • Publication number: 20110263849
    Abstract: Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.
    Type: Application
    Filed: December 25, 2009
    Publication date: October 27, 2011
    Applicants: GIFU UNIVERSITY, RIKEN
    Inventors: Masaaki Suzuki, Hisashi Doi, Hiroko Koyama
  • Patent number: 7227040
    Abstract: A branched composition can be formed by reacting a reagent containing a saturated hydrocarbon moiety in the presence of (a) a catalyst capable of activating a carbon-hydrogen bond therein and (b) a branching reagent having a moiety that binds to the carbon atom in the carbon-hydrogen bond upon extraction of the hydrogen atom from that carbon-hydrogen bond. Suitable catalysts are those that comprise a transition metal cation possessing multiple oxidation states that is embedded in an anion that is a transition metal oxide possessing a higher oxidation state for the metal therein than the metal in the cation.
    Type: Grant
    Filed: June 7, 2004
    Date of Patent: June 5, 2007
    Assignee: Akzo Nobel N.V.
    Inventors: Zongchao Zhang, Xiaolei Sun
  • Patent number: 7026478
    Abstract: A process for the production of compounds Ar—R1 by means of a cross-coupling reaction of an organometallic reagent R1-M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.
    Type: Grant
    Filed: May 10, 2002
    Date of Patent: April 11, 2006
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Alois Fürstner, Andreas Leitner, María Méndez
  • Patent number: 6878801
    Abstract: Novel polythiophenes which exhibit strong main chain absorption in the ultraviolet to visible region, show optical activity depending on the polymeric chain alone, and comprise as repeating units thiophene rings containing chiral substituent groups, and are represented by the following general formula: (wherein R1 and R2 are the same or different, each representing a hydrogen atom or an organic group, of which at least one is an enantiopure alkyl group with a branch structure at the ?-position, and n represents the number of repeating units selected from 10 to 100,000).
    Type: Grant
    Filed: January 8, 2003
    Date of Patent: April 12, 2005
    Assignees: Japan Science and Technology, Nippon Telegraph and Telephone Corporation
    Inventors: Michiya Fujiki, Hiroshi Nakashima, Julian R. Koe, Masao Morita, Hiromi Tamoto
  • Patent number: 5512685
    Abstract: The invention relates to a process for the preparation of 3-substituted thiophenes in which the substituent is a C.sub.4 -C.sub.18 -alkyl group. According to the invention, the preparation is carried out by allowing an alkali metal salt of a C.sub.4 -C.sub.18 -alkyl-succinic acid to react with a compound of sulfur and phosphorus, e.g. tetraphosphorus decasulfide, in an organic solvent at a temperature of 100.degree.-180.degree. C., the product obtained being 3-(C.sub.4 -C.sub.18 -alkyl)thiophene. The said reaction may be the last step in a process in which the initial material is maleic acid anhydride with which .alpha.-C.sub.4 -C.sub.18 -alkene is combined so that C.sub.4 -C.sub.18 -alkenylsuccinic acid anhydride is obtained, whereafter this is hydrogenated catalytically to produce C.sub.4 -C.sub.18 -alkylsuccinic acid anhydride. This is thereafter reacted with an alkali metal hydroxide so that an alkali salt of the C.sub.4 -C.sub.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: April 30, 1996
    Assignee: Neste Oy
    Inventors: Hannele Jarvinen, Leila Lahtinen, Osmo Hormi, Jan Nasman, Anna-Liisa Tammi
  • Patent number: 5395538
    Abstract: Alkylated thiophene compounds are high temperature stable lubricant fluids having excellent thermal stability, antiwear and load-carrying properties and excellent additive solubility.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: March 7, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Leslie R. Rudnick, Carleton N. Rowe
  • Patent number: 4783541
    Abstract: The invention relates to a process for isomerizing alkylthiophenes on zeolite catalysts. In particular, methylthiophene and ethylthiophene can be isomerized by this process. Suitable zeolites are in particular synthetic zeolites of the pentasil, mordenite of faujasite type in their acid form.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: November 8, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus Eichler, Ernst I. Leupold
  • Patent number: 4179580
    Abstract: A process for increasing the reaction rate of condensation reactions which occur between non-conjugated non-aromatic olefinically unsaturated hydrocarbons and active hydrogen-containing organic compounds in the presence of alkali metal comprising carrying out the reaction in the presence of titanium metal.
    Type: Grant
    Filed: May 11, 1978
    Date of Patent: December 18, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Raymond L. Cobb