2-Aminothiophenol → 2-(2-Aminophenyl)sulfanylbenzonitrile

HRID 974801Notes

Reaction equation

HRID 974801 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][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>C1COCC1>[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][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 24758Sodium hydrideHCID 678552-Fluorobenzonitrile

Product 1

HCID 3662332-(2-Aminophenyl)sulfanylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Aminothiophenol (6.26 g, 50 mmol) was dissolved in dry THF (50 ml) and sodium hydride (2 g of 60% dispersion, 1 eq) added with stirring at 0° C. under nitrogen. After stirring for 0.5 hr this mixture was added portionwise to a stirred solution of 2-fluorobenzonitrile (1eq) in THF (30 ml). The mixture was allowed to warm to room temperature overnight and then evaporated in vacuo and the residue purified by chromatography on silica, eluting with dichloromethane. The title compound was obtained as an off-white solid (5.27 g).

Workup

  1. stirringAfter stirring for 0.5 hr this mixture
  2. temperatureto warm to room temperature overnight
  3. customevaporated in vacuo
  4. customthe residue purified by chromatography on silica
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8eb42441d8cb4b86bc09c7eedd4d9a7a
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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