Reaktion #961344

Reaktionsgleichung

α-Bromophenylacetonitrile

N-acetylthiourea

→

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

Ausbeute 23.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for 3.5 hr
3. 3
   EinengenThe cooled mixture was concentrated in vacuo
4. 4
   Sonstigepartitioned between dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   WaschenThe organic phase was washed with brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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%).

Quelle