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

HRID 974812

Reaction equation

HRID 974812 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3af0e8c6284b4607843b6581cc8fb7d0
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Linked notes

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