Water → 3-Ethoxycarbonyl-5,8-difluoro-4-(3-trifluoromethylphenylmercapto)quinoline

HRID 266074

반응식

HRID 266074 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:17]([O:16][C:14]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[S:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:19])([F:28])[F:29])[CH:22]=1)=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[F:13])=[O:15])[CH3:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1367513-(Trifluoromethyl)benzenethiolHCID 17040076Ethyl 4-chloro-5,8-difluoroquinoline-3-carboxylate

생성물 1

HCID 28010183-Ethoxycarbonyl-5,8-difluoro-4-(3-trifluoromethylphenylmercapto)quinoline수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The reaction mixture of 100.0 mg (0.37 mmol) of 4-chloro-3-ethoxycarbonyl-5,8-difluoroquinoline, 80.3 mg (0.44 mmol) of 3-trifluoromethylthiophenol and 80 μL of diisopropylethylamine in 2.0 mL of N,N-dimethylformamide was stirred at room temperature for 2 h and cooled. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate and concentrated. The resulting residue was purified on silica gel column eluting with ethyl acetate-hexane (1:3) to give 30.0 mg (20%) of the title compound.

후처리

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified on silica gel column
  7. washeluting with ethyl acetate-hexane (1:3)

출처 및 근거

ORD 기록
ord-f9cd45ab8dd54a679adfeff65ba01e40
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650415

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