Reaction #1726704

Reaction equation

α-Bromophenylacetonitrile

N-acetylthiourea

→

2-(acetylamino)-4-amino-5-phenylthiazole

Yield 23.1%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 3.5 hr
3. 3
   ConcentrationThe cooled mixture was concentrated in vacuo
4. 4
   Otherpartitioned between dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   WashThe organic phase was washed with brine
6. 6
   Dryingdried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo

Procedure

α-Bromophenylacetonitrile (1.08 g, 5.48 mmol) in ethanol (10 ml) was treated with N-acetylthiourea (649 mg, 5.49 mmol) at ambient temperature for 4 hr, and then heated to reflux for 3.5 hr. The cooled mixture was concentrated in vacuo and then partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(acetylamino)-4-amino-5-phenylthiazole (295 mg, 23%).

Source