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

HRID 1082074

反応式

HRID 1082074 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-41f95da196dc4a58af01338051334978
出典データセット
uspto-grants-1996_12
特許番号
US05589474

関連ノート

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