Réaction #1726704

Équation de réaction

α-Bromophenylacetonitrile

N-acetylthiourea

→

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

Rendement 23.1%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureto reflux for 3.5 hr
3. 3
   ConcentrationThe cooled mixture was concentrated in vacuo
4. 4
   Autrepartitioned between dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   LavageThe organic phase was washed with brine
6. 6
   Séchagedried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo

Mode opératoire

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