Reacción #1726704

Ecuación de reacción

α-Bromophenylacetonitrile

N-acetylthiourea

→

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

Rendimiento 23.1%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 3.5 hr
3. 3
   ConcentraciónThe cooled mixture was concentrated in vacuo
4. 4
   Otropartitioned between dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   LavadoThe organic phase was washed with brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

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%).

Fuente