KR840000466A - Method for producing waste oxybenzoic acid derivative containing sulfonamide group - Google Patents

Method for producing waste oxybenzoic acid derivative containing sulfonamide group Download PDF

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KR840000466A
KR840000466A KR1019820003344A KR820003344A KR840000466A KR 840000466 A KR840000466 A KR 840000466A KR 1019820003344 A KR1019820003344 A KR 1019820003344A KR 820003344 A KR820003344 A KR 820003344A KR 840000466 A KR840000466 A KR 840000466A
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carbon atoms
alkyl
formula
reaction
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KR1019820003344A
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KR880002591B1 (en
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아이 헤이바 엠-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
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    • 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
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • 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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    • C07C303/36—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
    • 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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    • C07C303/36—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
    • C07C303/40—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 reactions not involving the formation of sulfonamide groups
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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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    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
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    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
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    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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    • C07C323/18—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
    • 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 없음No content

Description

술폰아미드기를 함유하는 폐녹시벤조산 유도체의 제조방법Method for producing waste oxybenzoic acid derivative containing sulfonamide group

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

Claims (16)

하기식(Ⅱ)의 할 로겐화물을 산수용체부재하 하기식(Ⅰ) 생성물의 분해온도 이하의온도인, 반응 매질로부터 히드라시드 부산물이 제거되는 온도에서 하기식(Ⅲ)의 술폰아미드와 반응시킴을 특징으로 하는 하기식(Ⅰ)의 술폰아미드기 함유 페녹시벤조산유도체 및 그의 염의 제조 방법.The halide of formula (II) is reacted with sulfonamide of formula (III) at a temperature at which the hydroxide by-product is removed from the reaction medium, which is at or below the decomposition temperature of the product of formula (I) without acid acceptor. A process for producing a sulfonamide group-containing phenoxybenzoic acid derivative of the following formula (I) and a salt thereof: 여기서, A는 수소, 플루오로, 염소, 브롬, 요오드, 니트로기, -N=NCF3, PO3H2및 탄소원자수 1~4의 그의에스테르류, NH2, NHOH, N2 +, 카르복실기 또는 그의 기능 유도체류, 모노알킬아미노, 또는 디알킬아미노기, NH-CO-R1기(여기서, R1은 알킬, 알콕시, 모노알킬아미노 또는 디알킬아미노기), 알킬기, 트리알킬암모니오, NHSO2R2(여기서, R2는 알킬 또는 페닐기), NHCONHSO2R2(여기서, R2는 전술한 바와 같음), 알킬티오, 알킬술피닐, 알킬술포닐, 디알킬술포니오, 시아노술포닐, 히드록실, 알카노일옥시알콕시, 알콕시카르보닐 치환 알콕시, SH, 니트로소, -SCN, 아지드, CF3,또는 아실이고; B는 수소, 플루오로, 염소, 브롬, 요오드, 알킬, 알콕시, 알킬피닐 또는 알킬술포닐기, CF2, NO2, CN, NH2, NHCOR1(여기서, R1은 상기와 동일함) 또는 CONH2이고; C는 수소, 할로겐 또는 알킬 또는 디알킬아미노기이고; D는 플루오로, 염소, 브롬, 요오드 또는 CF3, 알킬디오, 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 B에서와 동일하며; R은 -CON(R4)SO2R3(여기서, R4는 수소 또는 탄소원자수 1~4의 알킬기)이고; R3은 페닐, 피리딜 또는 1개 이상의 할로겐 원자로 임의 치환된 티에닐기, 알킬기 또는 니트로기, 탄소원자수 2~4의 알케닐 또는 알킬닐기, 또는 1종이상의 플루오로, 염소브롬 또는 요오드 원자, 바람직하게는 CF3에 의해 치환되었거나, 카르복실탄소원자수 2~5의 알콕시카르보닐, 탄소원자수, 2~5의 알킬카르보닐, 모노알킬카르바모일 또는 디알킬카르바모일(여기서, 알킬기는 탄소원자수 1~4를 가짐)에 의해 치환된 탄소원자수 1~4의 알킬기, 각각 탄소원자수 1~4인 알킬티오, 알킬술피닐, 알킬술포닐, 탄소원자수 2~5의 알킬카르보닐옥시, 탄소원자수 2~5의 카르보닐아미노 또는 시아노이고; X는 염소, 브롬 또는 요오드 원자를 나타낸다.Where A is hydrogen, fluoro, chlorine, bromine, iodine, nitro group, -N = NCF 3 , PO 3 H 2 and esters thereof having 1 to 4 carbon atoms, NH 2 , NHOH, N 2 + , carboxyl group or Functional derivatives thereof, monoalkylamino, or dialkylamino groups, NH-CO-R 1 groups, wherein R 1 is alkyl, alkoxy, monoalkylamino or dialkylamino groups, alkyl groups, trialkylammonios, NHSO 2 R 2 (where R 2 is an alkyl or phenyl group), NHCONHSO 2 R 2 (where R 2 is as described above), alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonio, cyanosulfonyl, hydroxide Hydroxyl, alkanoyloxyalkoxy, alkoxycarbonyl substituted alkoxy, SH, nitroso, -SCN, azide, CF 3 , Or acyl; B is hydrogen, fluoro, chlorine, bromine, iodine, alkyl, alkoxy, alkylpinyl or alkylsulfonyl group, CF 2 , NO 2 , CN, NH 2 , NHCOR 1 , where R 1 is the same as above or CONH 2 ; C is hydrogen, halogen or an alkyl or dialkylamino group; D is a fluoro, chlorine, bromine, iodine or CF 3 , alkyldio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, sulfamoyl, formyl, alkylcarbonyl, CN or dimethylamino group; E is hydrogen, halogenoalkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CN, CF 3 , NH 2 , CONH 2 or NH-CO-R 1 , wherein R 1 is as described above; F is the same as in B; R is -CON (R 4 ) SO 2 R 3 , wherein R 4 is hydrogen or an alkyl group having 1 to 4 carbon atoms; R 3 is phenyl, pyridyl or thienyl, alkyl or nitro group optionally substituted with one or more halogen atoms, alkenyl or alkylyl groups of 2 to 4 carbon atoms, or one or more fluoro, chlorine bromine or iodine atoms, preferably Preferably substituted by CF 3 , alkoxycarbonyl having 2 to 5 carboxyl carbon atoms, carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl, wherein the alkyl group is carbon atom Alkyl group having 1 to 4 carbon atoms substituted with 1 to 4 carbon atoms, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy having 2 to 5 carbon atoms, and 2 having 2 to 5 carbon atoms, respectively. ˜5 carbonylamino or cyano; X represents a chlorine, bromine or iodine atom. 제1항에 있어서, 반응이 과량의 식(Ⅱ)의 산할라이드 존재하 수행됨을 특징으로 하는 방법.The process according to claim 1, wherein the reaction is carried out in the presence of an excess of an acid halide of formula (II). 제2항에 있어서, 식(Ⅱ)의 산할로겐화물 1식(Ⅲ)의 술폰아미드의 몰비가 1.5~5임을 특징으로 하는 방법.The method according to claim 2, wherein the molar ratio of the sulfonamide of the acid halide formula (III) of formula (II) is 1.5-5. 제2 또는 3항 중의 어느 하나에 있어서, 반응 온도가 80~200℃, 바람직하게는 90~160℃임을 특징으로 하는 방법.The method according to claim 2, wherein the reaction temperature is 80-200 ° C., preferably 90-160 ° C. 5. 제1항에 있어서, 반응이 과량의 술폰아미드 존재하 수행됨을 특징으로 하는 방법.The process according to claim 1, wherein the reaction is carried out in the presence of excess sulfonamide. 제5항에 있어서, 식(Ⅲ)의 술폰아미드 (식(Ⅱ)의 산할라이드의 몰비가 1.5~5임을 특징으로 하는 방법.A process according to claim 5, wherein the molar ratio of sulfonamides of formula (III) (acid halides of formula (II) is 1.5-5). 제5 또는 6항 중의 어느 하나에 있어서, 반응 온도가 90~200℃, 바람직하게는 140~160℃임을 특징으로 하는 방법.The process according to claim 5, wherein the reaction temperature is 90-200 ° C., preferably 140-160 ° C. 8. 제1~7항 중의 어느 하나에 있어서, 반응이 반응 온도 이상의 b.p. 점을 갖는 용매 존재하 수행됨을 특징으로 하는 방법.The process according to any one of claims 1 to 7, wherein the reaction is at least b.p. Characterized in that it is carried out in the presence of a solvent having a point. 제8항에 있어서, 용매가 탄화수소임을 특징으로 하는 방법.The method of claim 8 wherein the solvent is a hydrocarbon. 제9항에 있어서, 용매가 큐멘이고 온도가 130-150℃임을 특징으로 하는 방법.10. The method of claim 9, wherein the solvent is cumene and the temperature is 130-150 ° C. 제1~8항중의 어느 하나에 있어서, 반응이 각 반응에서 촉매성질을 갖는 용매 존재하 수행됨을 특징으로 하는 방법.The process according to any one of claims 1 to 8, wherein the reaction is carried out in the presence of a solvent having catalytic properties in each reaction. 제11항에 있어서, 용매가 디메틸포름아미드 또는 디메틸아세타미드이고, 온도가 80℃~용매의 비점임을 특징으로 하는 방법.The method according to claim 11, wherein the solvent is dimethylformamide or dimethylacetamide, and the temperature is 80 ° C to the boiling point of the solvent. 제12항에 있어서, 온도가 90℃이상임을 특징으로 하는 방법.13. The method of claim 12, wherein the temperature is at least 90 ° C. 제1항 중의 어느 하나에 있어서, 식(Ⅰ) 및 (Ⅱ)중의 B 및 X는 염소원자이고, A는 염소원자 또는 NO2이고, C, E 및 F는 수소원자이고, D는 CF3임을 특징으로 하는 방법.2. The compound of claim 1, wherein B and X in formulas (I) and (II) are chlorine atoms, A is a chlorine atom or NO 2 , C, E and F are hydrogen atoms, and D is CF 3 How to feature. 제6 또는 7항 중의 어느 하나에 있어서, 술폰아미드는 R3가 알킬 또는 CF3기, 바람직하게는 메틸기임을 특징으로 하는 방법.The process according to claim 6, wherein the sulfonamide is characterized in that R 3 is an alkyl or CF 3 group, preferably a methyl group. 제1~15항중의 어느 하나에, 있어서 하기 식 화합물을 CH3-SO2-NH2와 반응시킴을 특징으로 하는 방법.The method according to any one of claims 1 to 15, wherein the following compound is reacted with CH 3 -SO 2 -NH 2 . ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR8203344A 1981-07-27 1982-07-27 Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group KR880002591B1 (en)

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