KR940011446A - 2-아릴-5-트리플루오로메틸 피롤 화합물의 제조방법 - Google Patents

2-아릴-5-트리플루오로메틸 피롤 화합물의 제조방법 Download PDF

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KR940011446A
KR940011446A KR1019930025148A KR930025148A KR940011446A KR 940011446 A KR940011446 A KR 940011446A KR 1019930025148 A KR1019930025148 A KR 1019930025148A KR 930025148 A KR930025148 A KR 930025148A KR 940011446 A KR940011446 A KR 940011446A
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South Korea
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alkyl
hydrogen
general formula
elevated temperature
haloamine
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KR1019930025148A
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English (en)
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KR100305288B1 (ko
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카메스워렌 벤카타라만
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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Priority claimed from US07/981,626 external-priority patent/US5225568A/en
Priority claimed from US07/989,271 external-priority patent/US5256796A/en
Application filed by 알퐁스 아아르 노에, 아메리칸 사이아나밋드 캄파니 filed Critical 알퐁스 아아르 노에
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Publication of KR100305288B1 publication Critical patent/KR100305288B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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
    • C07D207/42—Nitro radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

살충제, 진드기 박멸체 및 선충류 박멸제로서 및 상기 약제의 제조에서 중간체로서 유용한 2-아릴-5-트리플루오로메틸 피롤 화합물의 제조 방법을 제공한다.

Description

2-아릴-5-트리플루오로메틸 피롤 화합물의 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식 Ⅱ의 할로엔아민을
    (식에서 Y는 Cl, Br 또는 I이고; A는 수소 또는 페닐로 임의로 치환된 C1-C6아킬이고; W는 CN, NO2, CO2R1또는 SO2R1이고; L은 수소, F, Cl, Br 또는 1이고; M 및 R은 각각 독립적으로 수소, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, CN, F Cl, Br, I, NO2, R3CF2Z, R4CO 또는 NR5R6이고 M 및 R이 인접 위치상에 있을 때 그들이 결합된 탄소 원자와 함께 취해져서 MR이 -OCH2O-, -OCF2O- 또는 -CH〓CH-CH〓CH- 로 표현되는 고리를 형성한다.) 산존재하에서 및 임의로 용매존재하에서 약 1몰 당량의 트리플루오로아세톤 또는 C1-C4알킬 트리플루오로아세트아세테이트와 반응시키는 것으로 구성되는 하기 일반식 Ι의 2-아릴-5-트리플루오로메틸 피롤 화합물의 제조 방법.
    식에서 A, W, L, M 및 R은 상기 서술한 바와 같고, X는 수소 또는 CO2R2이고; R1은 C1-C6알킬, C3-C6시클로알킬 또는 페닐이고; R2는 C1-C4알킬이고; R3는 수소, F, CHF2, CHFCl 또는 CF3이고; R4는 C1-C4알킬 C1-C4알콕시 또는 NR5R6이고; R6는 수소 또는 C1-C4알킬이고; R5는 수소, C1-C4알킬 또는 R7CO이고; R7은 수소 또는 C14-C4알킬이고; Z는 S(O)n 또는 0이고; 및 n은 0, 1 또는 2중의 정수이다.
  2. 제1항에 있어서, 반응이 승온에서 일어나는 방법.
  3. 제1항에 있어서, 산이 아세트산인 방법.
  4. 제1항에 있어서, 일반식Ⅱ 할로엔아민을 약 1몰 당량의 트리플루오로아세톤 과 반응시키는 방법.
  5. 제1항에 있어서, 일반식Ⅱ 할로엔아민을 약 1몰 당량의 C1-C4알킬 트리플루오로아세테이트와 반응시키는 방법.
  6. 제2항에 있어서, 승온이 약60℃ 내지 250℃인 방법.
  7. 제3항에 있어서, 반응이 약70℃ 내지 180℃의 승온에서 일어나는 방법.
  8. 제4항에 있어서, 반응이 약70℃ -180℃ 승온에서 일어나는 방법.
  9. 제1항에 있어서, W가 CN인 방법.
  10. 제9항에 있어서, A가 수소 또는 C1-C6알킬인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930025148A 1992-11-25 1993-11-24 2-아릴-5-트리플루오로메틸피롤화합물의제조방법 KR100305288B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US07/981,626 US5225568A (en) 1992-11-25 1992-11-25 Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds
US07/981,626 1992-11-25
US07/989,271 US5256796A (en) 1992-12-11 1992-12-11 Method for the preparation of 2-aryl-5-trifluoromethylpyrrole compounds
US07/989,271 1992-12-11

Publications (2)

Publication Number Publication Date
KR940011446A true KR940011446A (ko) 1994-06-21
KR100305288B1 KR100305288B1 (ko) 2001-12-28

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KR1019930025148A KR100305288B1 (ko) 1992-11-25 1993-11-24 2-아릴-5-트리플루오로메틸피롤화합물의제조방법

Country Status (17)

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EP (1) EP0599036B1 (ko)
JP (1) JP3240232B2 (ko)
KR (1) KR100305288B1 (ko)
CN (1) CN1038412C (ko)
AT (1) ATE146457T1 (ko)
AU (1) AU669227B2 (ko)
BR (1) BR9304801A (ko)
CA (1) CA2109741A1 (ko)
CZ (1) CZ284072B6 (ko)
DE (1) DE69306744T2 (ko)
DK (1) DK0599036T3 (ko)
ES (1) ES2095544T3 (ko)
GR (1) GR3022196T3 (ko)
HU (1) HU213037B (ko)
IL (1) IL107711A (ko)
MX (1) MX9307237A (ko)
SK (1) SK279499B6 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101111657B1 (ko) * 2010-01-28 2012-02-14 주식회사 패트론 코팅장치

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100358866C (zh) * 2004-04-08 2008-01-02 上海交通大学 含对强碱不稳定取代基的n-乙烯基取代吡咯的制备方法
CN102114430B (zh) * 2009-12-30 2013-06-05 上海睿智化学研究有限公司 催化剂、其制备方法及n-烷基吡咯衍生物的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5010098A (en) * 1987-07-29 1991-04-23 American Cyanamid Company Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
US5180734A (en) * 1990-11-30 1993-01-19 American Cyanamid Company Insecticidal and acaricidal diarylpyrrolecarbonitrile and diarylnitropyrrole compounds
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
US5151536A (en) * 1990-12-17 1992-09-29 American Cyanamid Company Process for the manufacture of pesticidal 1-(alkoxymethyl) pyrrole compounds
US5225568A (en) * 1992-11-25 1993-07-06 American Cyanamid Company Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101111657B1 (ko) * 2010-01-28 2012-02-14 주식회사 패트론 코팅장치

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HU9303332D0 (en) 1994-03-28
BR9304801A (pt) 1994-05-31
AU5190293A (en) 1994-06-09
AU669227B2 (en) 1996-05-30
ATE146457T1 (de) 1997-01-15
ES2095544T3 (es) 1997-02-16
SK279499B6 (sk) 1998-12-02
HUT65802A (en) 1994-07-28
EP0599036A1 (en) 1994-06-01
SK129093A3 (en) 1994-11-09
DE69306744D1 (de) 1997-01-30
EP0599036B1 (en) 1996-12-18
KR100305288B1 (ko) 2001-12-28
DK0599036T3 (da) 1997-01-06
CA2109741A1 (en) 1994-05-26
DE69306744T2 (de) 1997-04-10
CZ284072B6 (cs) 1998-08-12
IL107711A (en) 1997-08-14
IL107711A0 (en) 1994-02-27
MX9307237A (es) 1994-06-30
JPH06228090A (ja) 1994-08-16
JP3240232B2 (ja) 2001-12-17
GR3022196T3 (en) 1997-03-31
HU213037B (en) 1997-01-28
CZ242793A3 (en) 1994-06-15
CN1092764A (zh) 1994-09-28
CN1038412C (zh) 1998-05-20

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