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KR930006949B1 - 할로벤조니트릴의 제법 - Google Patents

할로벤조니트릴의 제법 Download PDF

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KR930006949B1
KR930006949B1 KR1019900012457A KR900012457A KR930006949B1 KR 930006949 B1 KR930006949 B1 KR 930006949B1 KR 1019900012457 A KR1019900012457 A KR 1019900012457A KR 900012457 A KR900012457 A KR 900012457A KR 930006949 B1 KR930006949 B1 KR 930006949B1
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halobenzonitrile
preparation
dichlorobenzonitrile
formula
compound
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KR1019900012457A
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KR920004336A (ko
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전기호
김찬구
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초당약품공업 주식회사
김동구
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음.

Description

할로벤조니트릴의 제법
본 발명은 의약 및 농약의 중간체로 유용한 할로벤조니트릴의 일종인 2, 5-디클로로벤조니트릴(Ⅰ)의 신규 제조방법에 관한 것이다.
Figure kpo00001
2, 5-디클로로벤조니트릴(Ⅰ)의 제조방법은 이미 공지된 사실로서, 프랑스 특허공개 제 1,343,178호(1963), 일본특허공개 제 68-05,386호 및 68-10,623호에 의하면, 폴리클로로톨루엔의 암옥시데이션으로 300℃이상의 고온이 필요한 뿐 아니라, 수율도 저조하였으며, 또 다른 방법으로, 독일특허 제 2,001,289(1970)호에 의하면, 1, 2, 4-트리클로로벤젠으로부터 퀴놀린 존재하에서 235℃에서 반응시켜 제조하는 방법이 기술되어 있으나, 유기반응에서 200℃를 넘으면, 고온 반응으로 간주되므로, 조작상의 어려움이 많으며, 복잡한 공정을 필요로 하였다.
본 발명의 목적은 이러한 문제점을 해결하기 위하여, 1, 4-디클로로-2-요도벤젠(Ⅱ)으로부터 비교적 편리한 조건에서 높은 수율로 목적화합물 2, 5-디클로로벤조니트릴(Ⅰ)을 합성하는 새로운 방법을 제공하는 것이다.
본 발명의 내용을 상세히 설명하면 다음과 같다. 구조식(Ⅱ)의 화합물과 시안화 제1구리(Ⅲ)와의 반응에서, 용매로서 N, N-디메틸아미드류, 즉, N, N-디메틸포름아미드 또는 N, N-디메틸아세트아미드를 사용하여, 반응온도 90-150℃에서 5-7시간이면 충분하였다. 1, 4-디클로로-2-요도벤젠(Ⅱ)를 용매 N, N-디메틸포름아미드를 사용하여, 120℃에서 6시간동안 반응시키므로서, 구조식(Ⅰ)의 화합물을 높은 수율로 얻을 수 있었다. 그러므로, 본 발명자들은 새로운 출발물질인 구조식(Ⅱ)의 화합물을 출발물질로 할 경우에 기존의 반응조건에 비해 크게 편리하여졌음을 발견하였다.
다음의 실시예로서 본 발명을 상세히 설명하나, 이 실시예가 본 발명을 제한하는 것은 아니다.
[실시예]
27.29g의 1, 4-디클로로-2-요도벤젠(Ⅱ)을 50ml의 N, N-디메틸포름아미드에 녹이고 9.85g의 시안화 제1구리(Ⅲ)를 가했다. 120℃에서 6시간동안 교반후 상온까지 냉각시키고 불용성 물질을 여과하여 제거했다. 여액을 200ml의 물과 500ml의 n=헥산으로 추출했다. 유기층을 합쳐서 100ml의 물과 20ml의 포화소금물로 각각 세척하고 감압증발시켰다. 여기서 얻어진 고체를 200ml의 수용성 에탄올로 재결정하여 14.80g의 2, 5-디클로로벤조니트릴(Ⅰ)을 백색결정으로 얻었다.
수율 : 86%
원소분석(C7H3Cl2N : 172.01)
계산치 : C ; 48.88, H ; 1.76, N ; 8.14
실측치 : C ; 48.20, H ; 1.66, N ; 8.10
I.R.스펙트럼(KBr정제)
2235cm-1(-C≡N).

Claims (2)

  1. 다음의 구조식(Ⅱ)의 화합물과 시안화 제1구리를 반응시켜서 구조식(Ⅰ)의 2, 5-디클로로벤조니트릴을 제조하는 방법.
    Figure kpo00002
  2. 제1항에 있어서, 용매로서 아미드류(N, N-디메틸포름아미드, N, N-디메틸아세트아미드)를 사용함을 특징으로 하는 방법.
KR1019900012457A 1990-08-13 1990-08-13 할로벤조니트릴의 제법 KR930006949B1 (ko)

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KR1019900012457A KR930006949B1 (ko) 1990-08-13 1990-08-13 할로벤조니트릴의 제법

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KR1019900012457A KR930006949B1 (ko) 1990-08-13 1990-08-13 할로벤조니트릴의 제법

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KR930006949B1 true KR930006949B1 (ko) 1993-07-24

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