Phosgene → 9-[4-Chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

HRID 1646469노트

반응식

HRID 1646469 반응식
[C:1](Cl)(Cl)=[O:2].[CH3:5][O:6][C:7]([C:9]1([S:12][C:13]2[CH:18]=[C:17]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][NH:23]3)=[S:21])[C:16]([F:28])=[CH:15][C:14]=2[Cl:29])[CH2:11][CH2:10]1)=[O:8].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:29][C:14]1[C:13]([S:12][C:9]2([C:7]([O:6][CH3:5])=[O:8])[CH2:10][CH2:11]2)=[CH:18][C:17]([N:19]=[C:20]2[N:22]3[N:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[C:1](=[O:2])[S:21]2)=[C:16]([F:28])[CH:15]=1

참가 물질

5

반응물 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 867464931-[2-Chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester

생성물 1

HCID 198006209-[4-Chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

While stirring at a temperature of from 0° to +10° C., 5.7 ml of a 20% solution of phosgene in toluene are added dropwise to a solution of 3.7 g of 1-[2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester and 4.6 ml of triethylamine in 100 ml of toluene. The reaction mixture is then stirred for 4 hours and then introduced into ice-water. The organic phase is then separated off and dried over sodium sulfate. Concentration by evaporation and subsequent chromatographic purification by means of silica gel chromatography yield 3.7 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one, having a melting point of +149° C.

후처리

  1. customThe organic phase is then separated off
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration
  4. customby evaporation and subsequent chromatographic purification by means of silica gel chromatography yield 3.7 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

출처 및 근거

ORD 기록
ord-3e018f474b884c0da0559971f8a5f6f6
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180418

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