KR920002535A - 2-아릴-5-(트리플루오로메틸)피롤 화합물의 제조 방법 및 이를 위한 1,1,1-트리플루오로-2-프로펜 화합물 및 이의 제조방법 - Google Patents

2-아릴-5-(트리플루오로메틸)피롤 화합물의 제조 방법 및 이를 위한 1,1,1-트리플루오로-2-프로펜 화합물 및 이의 제조방법 Download PDF

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KR920002535A
KR920002535A KR1019910013135A KR910013135A KR920002535A KR 920002535 A KR920002535 A KR 920002535A KR 1019910013135 A KR1019910013135 A KR 1019910013135A KR 910013135 A KR910013135 A KR 910013135A KR 920002535 A KR920002535 A KR 920002535A
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compound
alkyl
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base
preparing
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윌리엄즈 애더 로저
오거스터스 퍼어치 조오지프
조오지 쿠운 데이빗
알프레드 마아틴 크레머 케니스
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/14—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/10—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and halogen atoms, or nitro or nitroso groups, bound to the same acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

내용 없음

Description

2-아릴-5-(트리플루오로메틸)피롤 화합물의 제조방법 및 이를 위한 1,1,1-트리플루오로-2-프로펜 화합물 및 이의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식:
    (상기식에서, W는 C1-C4-알킬, CF3또는 H이고, Y는 CN, NO2또는 CO2R이고, R은 C1-C4알킬이고, L은 H, F, Cl 또는 Br이고, M은 H, F, Cl, Br, I, CF3, NO2또는 OR1이며, R1은 C1-C3알킬 또는 C2F4H이다)을 갖는 첫번째 화합물을 형성시키기위한 방법으로서, 적어도 약 1몰 당량의 염기 및 극성 용매의 존재하에 하기 일반식:
    (상기식에서, L 및 M은 상기 기술된 바와 같음)을 갖는 두번째 화합물을 하기 일반식:
    (상기식에서, W 및 Y는 상기 기술된 바와 같고, X는 Cl, Br, I 또는임)을 갖는 적어도 약 1몰 당량의 세번째 화합물 및 이들의 시스 및 트란스 이성체와 반응시키는 것으로 구성된, 상기 첫번째 화합물의 제조 방법.
  2. 제1항에 있어서, 염기는 알카리 금속 탄산염, C1-C4트리알킬 아민 또는 피리딘이고, 극성 용매는 아세토니트릴, 디메틸포름아미드, 디메틸 설폭사이드, 에탄올, 메탄올 또는 이소프로판올인 방법.
  3. 제2항에 있어서, 염기가 트리에틸아민인 방법.
  4. 제2항에 있어서, 극성 용매가 아세토니트릴인 방법.
  5. 제2항에 있어서, 반응혼합물의 온도가 약 20°-180℃인 방법.
  6. 하기 일반식 :
    (상기식에서, X는 Cl, Br 또는 I이고; Z은 CN, CO2R 또는 C(O)R1이고, R 및 R1은 수소 또는 C1-C4알킬이다)을 갖는 화합물, 및 이들의 시스 및 트란스 이성체.
  7. 제6항에 있어서, X가 Cl 또는 Br 이고, Z은 CN 또는 C(O)R1이며, R1은 C1-C4알킬인 화합물.
  8. 제7항에 있어서, 3-브로모-5,5,5-트리플루오로-3-펜텐-2-온 또는 2-브로모-4,4,4-트리플루오로크로토노니트릴인 화합물.
  9. 용매의 존재하에 하기 일반식:
    (상기식에서, Z은 CN, CO2R 또는 C(O)R1이고, R 및 R1은 C1-C4알킬이다.)을 갖는 두번째 화합물 및 이들의 시스 및 트란스 이성체를 적어도 약2몰 당량의 할로겐 화제와 반응시켜서, 하기 일반식:F3CCHXCHXZ
    (상기식에서, X는 Cl, Br 또는 I이고:Z은 CN, CO2R 또는 C(O)R1이고, R 및 R1은 C1-C4알킬이다.)을 갖는 중간체 화합물을 산출시키고, 용매의 존재하에, 상기 중간체를 적어도 약1몰 당량의 염기와 반응시키는 것으로 구성된, 하기 일반식:
    (상기식에서, X 및 Z은 상기 기술된 바와 같음)을 갖는 첫번째 화합물의 제조방법.
  10. 제6항에 있어서, 염기가 트리에틸아민, 피리딘 또는 탄산나트륨이고; 할로겐화제가 브롬 또는 염소이며; 반응 용매가 테트라히드로푸란, 사염화 탄소 또는 에테르인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910013135A 1990-07-31 1991-07-30 2-아릴-5-(트리플루오로메틸) 피롤 화합물의 제조방법 및 이를 위한 1,1,1-트리플루오로-2-프로펜화합물 및 이의 제조 방법 KR100188325B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US07/560,396 1990-07-31
US07/560,403 US5068390A (en) 1990-07-31 1990-07-31 1,1,1-trifluoro-2-propene compounds
US07/560,403 1990-07-31
US07/560,396 US5030735A (en) 1990-07-31 1990-07-31 Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds
US7/560,396 1990-07-31

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KR920002535A true KR920002535A (ko) 1992-02-28
KR100188325B1 KR100188325B1 (ko) 1999-06-01

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CN (2) CN1030699C (ko)
AT (1) ATE118766T1 (ko)
AU (1) AU646480B2 (ko)
BR (1) BR9103255A (ko)
CA (1) CA2048042A1 (ko)
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DE (1) DE69107546T2 (ko)
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FI (1) FI102532B1 (ko)
GR (1) GR3015204T3 (ko)
HU (1) HU209916B (ko)
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IL (1) IL98235A (ko)
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US5128485A (en) * 1990-12-17 1992-07-07 American Cyanamid Company Synthesis of 2-aryl-5-(trifluoromethyl)pyrroles useful as pesticidal agents and as intermediates for the preparation of said agents
JP6089400B2 (ja) * 2009-02-13 2017-03-08 カリフォルニア インスティチュート オブ テクノロジー プラチナリッチ非晶質合金
CN102584667B (zh) * 2011-12-21 2013-12-18 湖南化工研究院 具生物活性的芳基吡咯类化合物及其制备方法
WO2018166819A1 (en) * 2017-03-13 2018-09-20 BASF Agro B.V. Production of arylpyrrol compounds in the presence of dipea base
CN112608268A (zh) * 2020-12-22 2021-04-06 李通 一种溶剂dmf替代乙腈生产溴虫腈中间体吡咯的方法
CN116987044B (zh) * 2023-09-28 2024-01-26 山东亿嘉农化有限公司 一种4－（对氯苯基）－2－三氟甲基－3－恶唑－5－酮的合成工艺

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CN1015626B (zh) * 1985-04-23 1992-02-26 鲁塞尔-于克拉夫公司 制备新的吡咯衍生物的方法
CN1026206C (zh) * 1987-07-29 1994-10-19 美国氰胺公司 杀虫、杀螨、杀线虫剂芳基吡咯及其组合物的制备方法
IL87222A (en) * 1987-07-29 1993-04-04 American Cyanamid Co Arylpyrroles, methods for thepreparation thereof andinsecticidal, acaricidal andnematicidal compositionscontaining them
US5010098A (en) * 1987-07-29 1991-04-23 American Cyanamid Company Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
US4929634A (en) * 1987-10-23 1990-05-29 American Cyanamid Company Method of and bait compositions for controlling mollusks
EP0358047A3 (en) * 1988-09-08 1991-05-29 American Cyanamid Company Method of controlling phytopathogenic fungi
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
IL92507A (en) * 1988-12-09 1994-06-24 Rhone Poulenc Agrochimie 1-Phenylpyrrole derivatives, process for their preparation and preparations against arthropods, nematodes of plants, worms and protozoa containing them
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US5157047A (en) * 1990-10-18 1992-10-20 American Cyanamid Company Bis- and tris(trifluoromethyl)arylpyrrole insecticidal and acaricidal agents

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BR9103255A (pt) 1992-02-18
CN1034933C (zh) 1997-05-21
CZ285271B6 (cs) 1999-06-16
FI913638A0 (fi) 1991-07-30
EP0469262A3 (en) 1992-07-01
EP0469262A2 (en) 1992-02-05
IE67178B1 (en) 1996-03-06
PT98477B (pt) 1999-09-30
JP3101012B2 (ja) 2000-10-23
KR100188325B1 (ko) 1999-06-01
ES2068425T3 (es) 1995-04-16
ATE118766T1 (de) 1995-03-15
CS237791A3 (en) 1992-02-19
HU912540D0 (en) 1992-01-28
FI102532B (fi) 1998-12-31
IL98235A0 (en) 1992-06-21
SK280893B6 (sk) 2000-09-12
FI102532B1 (fi) 1998-12-31
CA2048042A1 (en) 1992-02-01
PT98477A (pt) 1992-05-29
DE69107546T2 (de) 1995-09-28
FI913638A (fi) 1992-02-01
JPH04270263A (ja) 1992-09-25
HU209916B (en) 1994-11-28
IE912674A1 (en) 1992-02-12
HUT58287A (en) 1992-02-28
EP0469262B1 (en) 1995-02-22
GR3015204T3 (en) 1995-05-31
AU8151091A (en) 1992-02-06
DE69107546D1 (de) 1995-03-30
CN1030699C (zh) 1996-01-17
CN1119184A (zh) 1996-03-27
IL98235A (en) 1999-07-14
AU646480B2 (en) 1994-02-24
DK0469262T3 (da) 1995-03-27
SK280894B6 (sk) 2000-09-12
CN1058587A (zh) 1992-02-12

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