2-Aminothiophenol → HCID 19969463, compound

HRID 974809Notes

Reaction equation

HRID 974809 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-261cc5b59d4b4cfcb1d41aa11b6cc69b
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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