KR940011447A - 피롤의 탈브롬화에 의한 염소화 - Google Patents

피롤의 탈브롬화에 의한 염소화 Download PDF

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Publication number
KR940011447A
KR940011447A KR1019930025720A KR930025720A KR940011447A KR 940011447 A KR940011447 A KR 940011447A KR 1019930025720 A KR1019930025720 A KR 1019930025720A KR 930025720 A KR930025720 A KR 930025720A KR 940011447 A KR940011447 A KR 940011447A
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South Korea
Prior art keywords
hydrogen
alkyl
compound
optionally substituted
alkoxy
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KR1019930025720A
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English (en)
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케임즈와란 벤카타라만
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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Publication of KR940011447A publication Critical patent/KR940011447A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

피롤 핵상에서 염소로써의 브롬의 치환에 의한 전자 끄는 치환체를 함유하는 피롤 화합물의 염소화를 위한 단순한 경략적인 절차를 제공한다.

Description

피롤의 탈브롬화에 의한 염소화
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 촉매량의 브롬 존재하에서, 적어도 하나의 전자 끄는 치환체를 함유하는 피롤 화합물이 피롤 고리상에 어떤 브롬 치환제도 갖지 않을 때 및 용매 존재하에서 적어도 하나의 전자 끄는 치환체 및 적어도 하나의 수소 또는 브롬 치환체를 함유하는 피롤 화합물을 염소화제와 반응시키는 것으로 구성되는 염소화된 피롤 화합물의 제조방법.
  2. 제1항에 있어서, 상기 염소화된 피롤 화합물이 하기 일반식 Ι을 가지며:
    여기서 W는 CN, NO2, CO2R1, CONR2R3, CSNR4R5또는 S(O)nCF2R6이고; X는 Cl 또는 하나 내지 세 개의 C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, F, Cl, Br, I, CN, NO2, CF3, R7CF2B, R8CO 또는 NR9R10기로 임의 치환된 페닐이고; Y는 CF3, CL 또는 하나 내지 세개의 C1-C4일킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, F, CL, Br, I, CN, NO2, CF3, CF3, R7CF2B, R9CO 또는 NR9R10기로 임의로 치환된 페닐이고; Z는 Cl또는 CF3이고, 단, X, Y는 또는 Z중 적어도 하나는 Cl이어야 하고; A는 수소 또는 C1-C6알킬이고; R1은 C1-C6알킬, C3-C6시클로알킬, 또는 페닐이고; R2, R3, R4및 R5는 각각 독립적으로 수소, C1-C4알킬, C1-C4할로알킬 또는 하나이상의 Cl, Br, I, CN, NO2, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로 알콕시기로 임의 치환된 페닐이고; R6은 수소, F, Cl, Br, CF2H, CCI2H, CF3또는 CCI3이고; R7은 수소, F, CHF2, CHFCI또는 CF3이고; R8은 수소 또는 C1-C4알킬이고; R9은 수소 또는 C1-C4알킬이고; R10은 수소, C1-C4알킬 또는 R11CO이고; R11은 수소 또는 C1-C4알킬이고; B는 S(O)n또는 산소이고; 및 m 및 n은 각각 독립적으로 0,1, 또는 2의 정수이다; 이는 용매 존재하에서, 및 하기 L,M 및 R이 Br이 아닐 때, 촉매량의 브롬 존재하에서, 하기 일반식 Ⅱ의 화합물을 염소화제와 반응시키는 것으로 구성된다:
    식에서 L은 수소, Br 또는 하나 내지 세 개의 C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, F, Cl, Br, I, NO2, CF3, R7CF2B, B8CO 또는 NR9R10기로 임의 치환된 페닐이고; M은 수소, Br, CF3또는 하나 내지 세 개의 C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, F, Cl, Br, I, NO2,CF3, R7CF2B, B8CO 또는 NR9R10기로 임의 치환된 페닐이고; R은 수소 또는 Br 또는 CH3이고, 단 L,M또는 R중 적어도 하나는 수소 또는 브롬이어야 하고; 및 W, A, R7, R8, R9및 R10은 상기 서술한 바와 같은 방법.
  3. 제2항에 있어서, L, M 또는 R중 적어도 하나는 Br이고, 용매가 사염화 탄소인 방법.
  4. 제2항에 있어서, L, M 및 R이 Br이 아니고 용매가 클로로벤젠인 방법.
  5. 제3항에 있어서, A가 C1-C6알킬인 방법.
  6. 제4항에 있어서, A가 수소인 방법.
  7. 제2항에 있어서, 염소화제가 염소기체, 설푸릴 클로라이드, N-클로로숙신아미드 및 t-부틸히포클로리트로부터 선택되는 방법.
  8. 제2항에 있어서, W 및 CN이고, X는 Cl 또는 Br이고, Y는 Cl 또는 하나 내지 세 개의 Cl, Br, I 또는 CF3기로 임의 치환된 페닐이고, 및 Z는 CF3또는 Cl인 일반식 Ι의 화합물의 제조방법.
  9. 제8항에 있어서, A가 메틸인 방법.
  10. 제8항에 있어서, A가 수소인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930025720A 1992-11-30 1993-11-29 피롤의 탈브롬화에 의한 염소화 KR940011447A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/983,204 US5449789A (en) 1992-11-30 1992-11-30 Debrominative chlorination of pyrroles
US07/983,204 1992-11-30

Publications (1)

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KR940011447A true KR940011447A (ko) 1994-06-21

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US (2) US5449789A (ko)
EP (1) EP0600157A1 (ko)
JP (1) JPH06247930A (ko)
KR (1) KR940011447A (ko)
CN (1) CN1091127A (ko)
AU (1) AU5201293A (ko)
BR (1) BR9304870A (ko)
CA (1) CA2110089A1 (ko)
CZ (1) CZ242693A3 (ko)
HU (1) HU211073B (ko)
IL (1) IL107801A0 (ko)
MX (1) MX9306604A (ko)
SK (1) SK129193A3 (ko)
ZA (1) ZA938919B (ko)

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US5449789A (en) * 1992-11-30 1995-09-12 American Cyanamid Company Debrominative chlorination of pyrroles
US6271392B1 (en) 1994-10-07 2001-08-07 Rhone-Poulenc Inc. Intermediates useful for the synthesis of 1-arylpyrrole pesticides
US5945538A (en) * 1996-06-28 1999-08-31 American Cyanamid Company Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles
US5750726A (en) * 1996-06-28 1998-05-12 American Cyanamid Company Process for the manufacture of 2-aryl-5-perfluoroalkylpyrrole derivatives and intermediates useful therefor
US5777132A (en) * 1996-06-28 1998-07-07 American Cyanamid Company Process for the manufacture of 2-aryl-5 perfluoroalkylpyrrole derivatives
US5925773A (en) * 1996-06-28 1999-07-20 American Cyanamid Company Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use thereof in the manufacture of insecticidal arylpyrroles
US6011161A (en) * 1998-02-09 2000-01-04 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoro-alkylmethyl)arylimidoyl chloride compounds
US5965773A (en) * 1998-02-09 1999-10-12 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(perfluoroalkylmethyl) arylimidoyl chloride compounds
US5817834A (en) * 1998-02-09 1998-10-06 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-(perfluoroalkyl-methyl) arylimidoyl chloride compounds
US6133455A (en) * 1998-02-09 2000-10-17 American Cyanamid Company Process for the preparation of 2-aryl-5(perfluoro-alkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds
GB9930750D0 (en) 1999-12-29 2000-02-16 Novartis Ag Organic compounds
US6320059B1 (en) 2000-03-07 2001-11-20 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds
PE20070182A1 (es) * 2005-07-29 2007-03-06 Wyeth Corp Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona
PE20070341A1 (es) * 2005-07-29 2007-04-13 Wyeth Corp Derivados de pirrol como moduladores del receptor de progesterona
EP3241826B1 (en) * 2009-02-25 2019-10-30 Takeda Pharmaceutical Company Limited Process for producing pyrrole compound
CN106687550B (zh) 2014-08-05 2020-08-21 三吉油脂株式会社 用于向基体赋予紫外线吸收能力和/或高折射率的添加剂及使用该添加剂的树脂部件
CN111170921A (zh) * 2020-02-26 2020-05-19 上海博黑生物科技有限公司 一种3-氯吡咯-2-甲酸甲酯的合成方法
CN114436932A (zh) * 2022-01-12 2022-05-06 山东潍坊双星农药有限公司 一种溴虫腈同系物的合成工艺

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BR8906202A (pt) * 1988-12-05 1990-09-25 American Cyanamid Co Processo e composicao para o controle de pragas de insetos,acaros e moluscos,composto para tal controle e processo para sua preparacao
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MX9306604A (es) 1994-05-31
HU9303381D0 (en) 1994-03-28
IL107801A0 (en) 1994-02-27
ZA938919B (en) 1994-08-02
EP0600157A1 (en) 1994-06-08
HUT65577A (en) 1994-07-28
AU5201293A (en) 1994-06-09
CA2110089A1 (en) 1994-05-31
CZ242693A3 (en) 1994-06-15
SK129193A3 (en) 1994-11-09
BR9304870A (pt) 1994-06-14
US5449789A (en) 1995-09-12
HU211073B (en) 1995-10-30
JPH06247930A (ja) 1994-09-06
US5563279A (en) 1996-10-08
CN1091127A (zh) 1994-08-24

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