2-Aminothiophenol → HCID 19969463, compound

HRID 1082069Notes

Reaction equation

HRID 1082069 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].F[C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[C:14]#[N:15]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 24758Sodium hydrideHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 19969463HCID 19969463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Aminothiophenol (6.26 g, 50 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-5-nitrobenzonitrile (8.3 g, 50 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 (sodium sulphate) and evaporation of the organic layer gave a residue which was separated from chloroform as bright yellow crystals (10.1 g, Rf 0.52 in 1:1 ethyl acetate/hexane).

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(sodium sulphate) and evaporation of the organic layer
  8. customgave a residue which
  9. customwas separated from chloroform as bright yellow crystals (10.1 g, Rf 0.52 in 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-da98fca7610e4b0bba98a616c0365c04
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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