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

HRID 1082062Notes

Reaction equation

HRID 1082062 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 (1 eq) 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-2334d2c121334383b9a6efb5b96e0b14
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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