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

HRID 266074

反応式

HRID 266074 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f9cd45ab8dd54a679adfeff65ba01e40
出典データセット
uspto-grants-1997_07
特許番号
US05650415

関連ノート

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