Sodium hydride → 2-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile

HRID 974812

反応式

HRID 974812 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[SH:12].[H-].[Na+].F[C:16]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[S:12][C:16]1[C:23]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 880422-Amino-4-(trifluoromethyl)benzenethiolHCID 5189742-Fluoro-3-(trifluoromethyl)benzonitrile

生成物 1

HCID 199694362-(2-Amino-4-trifluoromethylphenylthio)-3-trifluoromethylbenzonitrile収率 71.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

2-Amino-4-trifluoromethylthiophenol (5.74 g, 25 mmol) was added to a mixture of sodium hydride (2.0 g of 60% oil dispersion, 50 mmol) in DMF (100 ml) at 0° under nitrogen. After stirring for 30 minutes at 0°, 2-fluoro-3-trifluoromethylbenzonitrile (4.73 g, 25 mmol) in DMF (20 ml) was added and the mixture kept at room temperature overnight. The reaction mixture was evaporated and azeotroped with toluene, then the residue was partitioned between chloroform and water and the layers separated. Drying (magnesium sulphate) and evaporation of the organic layer gave a residue which was purified by chromatography on silica gel, eluting with dichloromethane. Recrystallisation from cyclohexane afforded the product as colourless needles (6.44 g).

後処理

  1. waitthe mixture kept at room temperature overnight
  2. customThe reaction mixture was evaporated
  3. customazeotroped with toluene
  4. customthe residue was partitioned between chloroform and water
  5. customthe layers separated
  6. customDrying
  7. custom(magnesium sulphate) and evaporation of the organic layer
  8. customgave a residue which
  9. customwas purified by chromatography on silica gel
  10. washeluting with dichloromethane
  11. customRecrystallisation from cyclohexane

出典と根拠

ORDレコード
ord-3af0e8c6284b4607843b6581cc8fb7d0
出典データセット
uspto-grants-1997_03
特許番号
US05607929

関連ノート

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