KR880002591B1 - 술폰아미드기를 함유하는 페녹시벤조산 유도체의 제조방법 - Google Patents

술폰아미드기를 함유하는 페녹시벤조산 유도체의 제조방법 Download PDF

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KR880002591B1
KR880002591B1 KR8203344A KR820003344A KR880002591B1 KR 880002591 B1 KR880002591 B1 KR 880002591B1 KR 8203344 A KR8203344 A KR 8203344A KR 820003344 A KR820003344 A KR 820003344A KR 880002591 B1 KR880002591 B1 KR 880002591B1
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formula
reaction
sulfonamide
solvent
alkyl
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KR8203344A
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KR840000466A (ko
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아이 헤이바 엘-아마디
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샤를르 브라쇼뜨
롱-쁘랑 아그로시미
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
    • A—HUMAN NECESSITIES
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    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
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    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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Abstract

내용 없음.

Description

술폰아미드기를 함유하는 페녹시벤조산 유도체의 제조방법
본 발명은 제초성을 갖는 술폰아미드기 함유 페녹시 벤조산 유도체의 개량된 제조 방법에 관한 것이다.
술폰아미드기 함유 페녹시벤조산의 제초성 유도체류는 유럽 특허출원 제3,416 및 23,392호에 공지되어 있다.
이들 특허출원에는 하기식(Ⅰ)의 생성물 및 그의 염이 기재되어 있다.
Figure kpo00001
여기에서, A는 수소, 불소, 염소, 브롬, 요오드, 니트로기, -N=NCF3, PO3H2및 탄소원자수 1~4의 그의 알킬에스테르류, NH2, NHOH2, N+ 2, 카르복실기 또는 그의 기능 유도체중의 어느 하나, 모노알킬아미노 또는 디알킬아미노기, NH-CO-R1(여기서, R1은 알킬, 알콕시, 모노알킬아미노 또는 디알킬아미노기이다), 알킬기, 트리알킬암모니오, NHSO2R2(여기서, R2는 알킬 또는 페닐기이다), NHCONHSO2R2(여기서, R2는 전술한 바와 같음), 알킬티오, 알킬술피닐, 알킬술포닐, 디알킬술포니오, 시아노술포닐, 히드록실, 알카노일옥시, 알콕시, 알콕시카르보닐로 치환된 알콕시, SH, 니트로소, -SCN, 아지드, CF3,
Figure kpo00002
또는 아실이고 ; B는 수소, 불소, 염소, 브롬, 요오드, 알킬, 알콕시, 알킬술피닐 또는 알킬술포닐기, CF3, NO2, CN, NH2, NHCOR1(여기서, R1은 전술한 바와 같음), 또는 CONH2이고 ; C는 수소, 할로겐 또는 알킬 또는 디알킬아미노기이고 ; D는 불소, 염소, 브롬, 요오드 또는 CF3, 알킬티오, 알킬술피닐, 알킬술포닐, 할로게노알킬, 술파모일, 포르밀, 알킬카르보닐, CN 또는 디메틸아미노기이며 ; E는 수소, 할로게노알킬, 알콕시, 알킬술피닐 또는 알킬술포닐기, CN, CF3, NH2, CONH2또는 NH-CO-R1(여기서, R1은 전술한 바와 같음)이고 ; F는 B에서 주어진 의미중의 하나이며 ; R은 -CON(R4)SO2R3이고, 여기서, R4는 수소 또는 탄소원자수 1~4의 알킬기이고, R3는 페닐, 피리딜 또는 1개 이상의 할로겐원자로 임의로 치환되는 티에닐기, 알킬기 또는 니트로기, 탄소원자수 2~4의 알케닐 또는 알키닐기 또는 탄소원자수 1~4의 알킬기[1개 이상의 불소, 염소, 브롬 또는 요오드 원자, 바람직하게는 CF3에 의해 치환되거나, 카르복실, 탄소원자수 2~5의 알콕시카르보닐, 탄소원자수 2~5의 알킬카르보닐, 모노알킬카르바모일 또는 디알킬카르바모일(여기서, 알킬기는 탄소원자수 1~4의 탄소원자임), 탄소원자수 2~5의 알킬카르보닐옥시, 탄소원자수 2~5의 알킬카르보닐아미노 또는 시아노에 의해 치환됨]를 나타낸다.
공지의 방법에 있어서, 상기 식(Ⅰ)의 생성물은 중간 물질인 하기식(Ⅱ)의 산 할로겐화물과 하기식(Ⅲ)의 술폰아미드를 산 수용체(특히, N,N-디메틸아닐린 또는 피리딘과 같은 3급 아민, 무수탄산칼륨과 같은 알칼리금속탄산염, 또는 플로오르화 칼슘과 같은 알칼리금속 플로오르화 물)존재하에서 25~140℃로 반응시켜 제조할 수 있다.
Figure kpo00003
상기 식중, X는 염소, 브롬 또는 요오드이고, A, B, C, D, E, F 및 R3는 전술한 바와 같다.
R4가 수소원자인 상기 식(Ⅰ)의 화합물은 예를 들어 탄소원자수 1~4의 디아조알칸과 반응시키는 공지의 방법에 의해 알킬화 시켜 R4가 탄소원자수 1~4의 알킬기인 상응 화합물을 얻을 수 있다.
일반식(Ⅱ) 및 (Ⅲ)의 생성물의 축합 방법은 다수의 결점을 가지고 있다. 즉, 수율이 평범하다(예 ; 유럽 특허출원 제23,392호의 실시예 14에서는 수율이 27%이고, 실시예 34에서는 9.5%이다). 그 이유는 디아실화 반응을 증진시킴으로써 수율을 저하시키는 산 수용체의 존재에 기인하는 것으로 추측된다. 또한, 산 수용체를 사용하게 되면 최종 생성물의 분리 및 정제가 어렵고 값이 비싸게 든다.
본 발명의 한가지 목적은 이들 결점을 극복하는 것이다.
본 발명에 다른 방법은 산 할로겐화물(바람직하게는 염화물, 브롬화물 또는 요오드화물)과 일반식(Ⅲ)의 술폰 아미드를 산수용체 부재하에서 할로겐화 수소산이 생성되는 경우 일반식(Ⅰ)의 반응생성물이 분해되지 않고 반응 매질로부터 할로겐화 수소산(HCl, HBr, HI)이 기체상태로 제거되는 온도에서 반응시키는 것으로 구성된다.
본 발명의 방법에 의해, 공지의 방법보다 더욱 간단한 방법에 의해 최종 생성물을 회수 및 정제하여 페녹시 벤조산의 술폰아미드 유도체류가 실질적으로 더 높은 수율로 수득될 수 있다(에 ; 약 30%이상, 통상의 경우 50%이상).
실제로는, 본 발명에서 사용되는 산 할로겐화물은 일반식(Ⅱ)의 산 할로겐화물이고, A가 NO2기 또는 플루오르, 염소, 브롬 또는 요오드 원자이고, B는 할로겐원자이고, C, E 및 F가 수소원자이며, D가 CF3기인식(Ⅱ)의 할로겐화물을 사용하는 것이 바람직하다. 또한, R3가 알킬기, 특히 CH3또는 CF3기인 식(Ⅲ)의 화합물의 술폰아미드류를 사용하는 것도 바람직하다.
본 발명 방법이 수행되는 온도는, 특히 일반식(Ⅱ)의 산 할로겐화물 또는 일반식(Ⅲ)의 술폰아미드가 과량이거나, 촉매 성질을 갖는 용매가 사용 또는 사용되지 않는가에 따라 다르다.
따라서, 만약 산 할로겐화물(Ⅱ)의 과량, 즉(Ⅱ)/(Ⅲ )의 몰비가 약 1.5~5인 경우에는 산 할로겐화물(Ⅱ)은 반응의 용매로서 작용하고, 반응 온도는 80~200℃이고, 바람직하게는 90~160℃이다.
미반응 산 할로겐화물(Ⅱ)은 특히 펜탄, 헥산, 헵탄, 시클로펜탄, 시클로헥산, 시클로헵탄, 벤젠, 톨루엔 또는 크실렌과 같은 탄화수소, 또 클로로벤젠류와 같은 할로겐화 탄화수소, CS2, 테트라히드로푸란, 디옥산 등과 같은 불활성 용매로 세척시킴으로써 반응 매질로부터 회수될 수 있다.
과량의 술폰아미드가 사용되는 경우, 즉 화합물(Ⅲ )/(Ⅱ)의 몰비가 1.5~5인 경우에는 반응 온도가 보통 90~200℃이고, 바람직하게는 140~160℃이다. 어느 경우에서나, 최소한 반응 매질을 용융시키기에 충분해야 한다. 과량의 술폰아미드(Ⅲ)은 물 또는 이 반응물(Ⅲ)에 비활성인 용매로 세척시켜 반응 매질로부터 회수될 수 있다.
반응물은 반응 온도 이상의 b.p.점을 갖는 불활성 용매(즉, 염소화 또는 비염소화 액체탄화수소, 예 ; 벤젠, 톨루엔, 크실렌, 크실렌 또는 큐멘의 혼합물)중에 용해시킬 수가 있는데, 이런 경우 최대 반응 온도가 용매의 b.p.점 바로 아래의 온도가 유리하다. 따라서, 약 153℃에서 비등하는 큐멘의 경우에는 반응은 130~150℃에서 바람직하게 수행된다. 불활성 용매를 사용하여 공업적인 규모로 제조하는 경우에는 열 전달이 더욱 양호하다는 실제적인 잇점에 있고, 또한 반응 매질의 국소 과열을 피할 수도 있다.
본 발명의 또 다른 변형에 따라 산 할라이드(Ⅱ)와 술폰아미드(Ⅲ)의 반응으로 페녹시벤조일 술폰아미드(Ⅰ)를 수득하는데 있어서 촉매작용을 갖는 용매를 사용한다. 디메틸포름아미드(=DMF, 약 154℃에서 비등) 및 디메틸아세타미드(=DMAC, 약 164℃에서 비등)는 특히 이 경우에 유리하고, 비교적 저온(예 : 80~120℃, 바람직하게는 90~110℃) 또는 이들 용매의 b.p.점 바로 아래의 고온에서도 사용할 수 있으며, 반응 속도는 더욱 빠르다.
실시예가 하기에 주어지는데, 여기에서는 본 발명을 제한함이 없이 설명되고, 본 발명이 어떻게 수행되는가가 예시된다.
[실시예 1]
메탄술폰아미드(2g ; 0.021몰)를 5-[2'-클로로-4'-(트리플루오로메틸)-페녹시]-2-니트로벤조일클로라이드(3.8g ; 0.01몰)와 섞는다. 이 혼합물을 150℃에서 20분간 가열시킨다. 염화수소가 생성되었을 때 이를 반응매질로부터 방출시킨다. 매질을 냉각시켜 블랙 오일을 수득하고 ; 이를 수산화나트륨 수용액에 용해시키고 ; 용액을 여과시키고, 여액을 묽은 HCl로 산성화하고, 일반식(Ⅳ)의 생성물은 침전시킨다. 이에 따라, 195~197℃에서 용융하고, 적외선 흡수 밴드를 1,692㎝-1(C=O 기)에서 갖는 생성물(3.1g)이 71%의 수율로 수득된다. 이 생성물은 하기 구조식을 갖는다.
Figure kpo00004
[실시예 2]
250g의 산 염화물 및 130g의 메탄술폰아미드를 사용하는 것을 제외하고, 실시예 1의 방법을 반복 실시한다. 혼합물을 냉각시킨 후에 이소프로판올로 재결정시키는 것에 의해 반응 생성물을 직접 분리시킨다. 이에따라, 일반식(Ⅳ)의 생성물이 64%(185g)의 수율로 수득된다. 이 생성물의 구조는 적외선(흡수밴드 : 1,692㎝-1) 및 핵자기 공명(단일선 3.5ppm, 다중선 8.07ppm)에 의해 확인된다.
산 수용체로서 피리딘을 사용하는 유럽 특허출원 제23,392호의 실시예의 방법을 이용하는 경우에는, 수율을 단지 25%이다.

Claims (16)

  1. 하기식(Ⅱ)의 산 할로겐화물을 산 수용체 부재하 하기식(Ⅰ) 생성물의 분해 온도 이하의 온도인, 반응 매질로부터 기체상의 히드라시드 부산물이 제거되는 온도에서 하기식(Ⅲ)의 술폰아미드와 반응시킴을 특징으로 하는 하기식(Ⅰ)의 술폰아미드기 함유 페녹시벤조산 유도체 및 그의 염의 제조방법.
    Figure kpo00005
    여기서, A는 수소, 니트로기 또는 할로겐원자이고 ; B는 할로겐원자이고 ; C는 수소이고 ; D는 CF3이고 ; E는 수소이고 ; F는 수소이고 ; R은 -CONHSO2R3(여기서, R3는 C1~C4알킬기이다)이고 ; X는 할로겐원자이다.
  2. 제 1 항에 있어서, 반응이 과량의 식(Ⅱ)의 산 할로겐화물 존재하 수행됨을 특징으로 하는 방법.
  3. 제 2 항에 있어서, 식(Ⅱ)의 산 할로겐화물/식(Ⅲ)의 술폰아미드의 몰비가 1.5~5임을 특징으로 하는 방법.
  4. 제2 또는 3항에 있어서, 반응 온도가 80~200℃임을 특징으로 하는 방법.
  5. 제 1 항에 있어서, 반응이 과량의 술폰아미드 존재하 수행됨을 특징으로 하는 방법.
  6. 제 5 항에 있어서, 식(Ⅲ)의 술폰아미드/식(Ⅱ)의 산 할라이드의 몰비가 1.5~5임을 특징으로 하는 방법.
  7. 제5 또는 6항에 잇어서, 반응 온도가 90~200℃임을 특징으로 하는 방법.
  8. 제 7 항에 있어서, 반응이 반응 온도 이상의 비점을 용매 존재하 수행됨을 특징으로 하는 방법.
  9. 제 8 항에 있어서, 용매가 탄화수소임을 특징으로 하는 방법.
  10. 제 9 항에 있어서, 용매가 큐멘이고 온도가 130~150℃임을 특징으로 하는 방법.
  11. 제 8 항에 있어서, 반응이 각 반응에서 촉매성질을 갖는 용매 존재하 수행됨을 특징으로 하는 방법.
  12. 제11항에 있어서, 용매가 디메틸포름아미드 또는 디메틸아세타미드이고, 온도가 80℃~ 용매의 비점임을 특징으로 하는 방법.
  13. 제12항에 있어서, 온도가 90℃ 이상임을 특징으로 하는 방법.
  14. 제13항에 있어서, 식(Ⅰ) 및 (Ⅱ)에서 B 및 X는 염소원자이고, A는 염소원자 또는 NO2이고, C,E 및 F는 수소원자이고, D는 CF3임을 특징으로 하는 방법.
  15. 제 7 항에 있어서, 술폰아미드는 R3가 C1~C4의 알킬기 임을 특징으로 하는 방법.
  16. 제15항에 있어서, 하기식 화합물을 CH3-SO2-NH2와 반응시킴을 특징으로 하는 방법.
    Figure kpo00006
KR8203344A 1981-07-27 1982-07-27 술폰아미드기를 함유하는 페녹시벤조산 유도체의 제조방법 KR880002591B1 (ko)

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