KR910700227A - Explosion-proof 1-dimethylamino-3-dimethylimino-2-arylprop-1-ene salts, preparation method and use thereof - Google Patents

Explosion-proof 1-dimethylamino-3-dimethylimino-2-arylprop-1-ene salts, preparation method and use thereof

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Publication number
KR910700227A
KR910700227A KR1019900701770A KR900701770A KR910700227A KR 910700227 A KR910700227 A KR 910700227A KR 1019900701770 A KR1019900701770 A KR 1019900701770A KR 900701770 A KR900701770 A KR 900701770A KR 910700227 A KR910700227 A KR 910700227A
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KR
South Korea
Prior art keywords
salt
formula
soluble
trimethine
naphthalene
Prior art date
Application number
KR1019900701770A
Other languages
Korean (ko)
Inventor
뮐러 잉그리드
헴머링 볼프강
빙겐 라이너
Original Assignee
오일러, 라피스
훽스트 아크티엔게젤샤프트
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 오일러, 라피스, 훽스트 아크티엔게젤샤프트 filed Critical 오일러, 라피스
Publication of KR910700227A publication Critical patent/KR910700227A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음.No content.

Description

방폭성1-디메틸아미노-3-디메틸이미노-2-아릴프로프-1-엔 염, 이들의 제조방법 및 용도.Explosion proof 1-dimethylamino-3-dimethylimino-2-arylprop-1-ene salts, their preparation and use.

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

제1도는 메탄올/디페틸 에테르(6:4 V/V)로 부터 재결정시켜 융점이 212℃(분해시작)인 분석적으로 순수한 화합물을 수득할수 있다. IR스펙트럼은 제1도에 나타내었다.Figure 1 can be recrystallized from methanol / dipetyl ether (6: 4 V / V) to give analytically pure compounds having a melting point of 212 ° C. (starting decomposition). IR spectrum is shown in FIG.

제2도는 메탄올로부터 재결정시켜, 융점이 268℃(분해시작)인 분석적으로 순수한 화합물을 수득할 수 있다. IR스펙트럼은 제2도에 나타내었다.Figure 2 can be recrystallized from methanol to give analytically pure compounds having a melting point of 268 DEG C (starting decomposition). IR spectrum is shown in FIG.

Claims (3)

방폭성이고, 수난용성인 하기 일반식(I)의 트리메틴 염;Trimethine salt of the following general formula (I) which is explosion-proof and poorly water-soluble; 상기식에서, R은 할로겐, (C1-C12)-알킬, (C1-C12)- 알콕시 또는 하이드록실에 의해 임의로 단일 또는 다중치환된 아릴 또는 헤테로아릴이고(여기에서, 아릴은 바람직하게 페닐, 나프틸, 비페닐릴, 안트라세닐 또는 테트랄리닐이며, 헤테로아릴은 바람직하게 피리디닐, 피리미디닐, 피라지닐 또는 피라다지닐이고, 할로겐은 바람직하게 F, 또는 C1 또는 Br, 특히 F는 C1이며, 라디칼(C1-C12)-알킬 및 (C1-C12)-알콕시는 할로겐, 특히 F 또는 C1에 의해 임의로 단일 또는 다중치환된다.):X는 비-산화성이며, 트리메틴 양이온에 대해 불활성이고, p-톨루엔설포네이트, 나프탈렌-2-설포네이트, 나트탈렌-1-설포네이트, 나트탈렌-1,5-디설포네이트, BF4 (-), SbF6 (-), PF(-), AIF6 (-), 특히, PF6 (-)및 나프탈렌-2-설포네이트중에서 선택된 수난용성인 트리메틴 염을 형성할수 있는 산 라디칼의 음이온 당량이다.Wherein, R is halogen, (C1-C 12) - alkyl, (C 1 -C 12) - alkoxy, or hydroxy, optionally singly or multiply by a hydroxyl substituted aryl or heteroaryl (wherein aryl is preferably phenyl , Naphthyl, biphenylyl, anthracenyl or tetralinyl, heteroaryl is preferably pyridinyl, pyrimidinyl, pyrazinyl or pyrazinyl, and halogen is preferably F, or C1 or Br, in particular F is C 1 , radicals (C 1 -C 12 ) -alkyl and (C 1 -C 12 ) -alkoxy are optionally mono- or polysubstituted by halogen, in particular F or C 1 ): X is non-oxidative Inert to cation, p-toluenesulfonate, naphthalene-2-sulfonate, naphthalene-1-sulfonate, naphthalene-1,5-disulfonate, BF 4 (-) , SbF 6 (-) , Can form poorly water-soluble trimethine salts selected from PF (-) , AIF 6 (-) , in particular PF 6 (-) and naphthalene-2-sulfonate. Is the anion equivalent of an acid radical. 하기 일반식(Ⅲ)의 산 또는 이들의 수용성 염을 수용성 일급 트리메틴 염을 함유하는 수성 반응 혼합물에 적어도 화학량론적 양으로 가하고, 생성된 일반식(Ⅰ)의 수난용성인 트리메틴 염을 분리시킴을 특징으로 하여, 빌스마이머-헤크(Vilsmeier-Haack) 반응 조건하에서, 하기 일반식(Ⅱ)의 화합물을 포밀화시키고, 이어서 수성 매질 내에서 포밀화 생성물을 가수분해시켜, 수용성 1급 트리메틸 염을 형성시킴으로써 제1항에서 청구된 일반식(Ⅰ)의 트리메틴 염을 제조하는 방법.An acid of formula (III) or a water-soluble salt thereof is added to the aqueous reaction mixture containing a water-soluble primary trimetine salt at least in stoichiometric amounts to separate the resulting poorly water-soluble trimethine salt of formula (I). Characterized in that, under Vilsmeier-Haack reaction conditions, the compound of formula II is formylated, and then the formylation product is hydrolyzed in an aqueous medium to obtain a water-soluble primary trimethyl salt. A process for preparing the trimethine salt of formula (I) as claimed in claim 1 by forming a compound. R-CH2-COOH (Ⅱ)R-CH 2 -COOH (II) (H)nX (Ⅲ)(H) n X (III) 상기식에서, R 및 X는 일반식(Ⅰ)에서 정의된 것과 같으며; n은 1내지 3, 바람직하게는 1 또는 2, 특히 1이다.Wherein R and X are as defined in formula (I); n is 1 to 3, preferably 1 or 2, in particular 1. 헤테로사이클, 바람직하게는 피리미딘 및 피리딘의 합성을 위한 제1항에서 청구된 일반식(Ⅰ)의 트리메틴염 또는 제2항에서 청구된 방법으로 제조된 트리메틴 염의 중간체로서의 용도.Use as a intermediate of a trimethine salt of formula (I) as claimed in claim 1 or a trimetine salt prepared by the method as claimed in claim 2 for the synthesis of a heterocycle, preferably pyrimidine and pyridine. ※참고사항:최초출원 내용에 의하여 공개하는 것임.※ Note: This is to be disclosed based on the first application.
KR1019900701770A 1988-12-14 1989-12-09 Explosion-proof 1-dimethylamino-3-dimethylimino-2-arylprop-1-ene salts, preparation method and use thereof KR910700227A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3842062A DE3842062A1 (en) 1988-12-14 1988-12-14 EXPLOSION-SAFE 1-DIMETHYLAMINO-3-DIMETHYLIMINO-2-ARYLPROPEN-1 SALTS, METHOD FOR THEIR PRODUCTION AND THEIR USE
DEP3842062.7 1988-12-14
PCT/EP1989/001510 WO1990006913A1 (en) 1988-12-14 1989-12-09 Explosion-proof 1-dimethylamino-3-dimethylimino-2-arylprop-1-ene salts, process for their preparation, and their use

Publications (1)

Publication Number Publication Date
KR910700227A true KR910700227A (en) 1991-03-14

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EP (1) EP0449917A1 (en)
JP (1) JPH04502158A (en)
KR (1) KR910700227A (en)
CA (1) CA2005330A1 (en)
DE (1) DE3842062A1 (en)
NO (1) NO912279L (en)
WO (1) WO1990006913A1 (en)

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Publication number Priority date Publication date Assignee Title
RS49945B (en) * 1998-04-24 2008-09-29 Merck & Co.Inc., Process for synthesizing cox-2 inhibitors

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* Cited by examiner, † Cited by third party
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US3288784A (en) * 1966-04-11 1966-11-29 Monsanto Co Method of preparing substituted chlorominium salts
US3993656A (en) * 1974-11-19 1976-11-23 Merck & Co., Inc. 1,8-Naphthyridine compounds
US4310670A (en) * 1980-02-26 1982-01-12 Sterling Drug Inc. Low-temperature, aqueous conversion of 4-picoline derivative to 5-cyano-[3,4'-bipyridin]-6(1H)-one
DE3173083D1 (en) * 1980-03-22 1986-01-16 Fbc Ltd Pesticidal heterocyclic compounds, processes for preparing them, compositions containing them, and their use
US4489011A (en) * 1983-05-16 1984-12-18 Merrell Dow Pharmaceuticals Inc. Hypoglycemic N-(2-substituted-3-dialkylamino-2-propenylidene)-N-alkylalkanaminium camsylate salts

Also Published As

Publication number Publication date
DE3842062A1 (en) 1990-06-28
EP0449917A1 (en) 1991-10-09
WO1990006913A1 (en) 1990-06-28
NO912279D0 (en) 1991-06-13
JPH04502158A (en) 1992-04-16
CA2005330A1 (en) 1990-06-14
NO912279L (en) 1991-06-13

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