反应 #1726704

ord-d7ddcf975d934cd196baeb7fb4c03fd9

反应方程式

N#CC(Br)c1ccccc1
α-Bromophenylacetonitrile
CC(=O)NC(N)=S
N-acetylthiourea
CC(=O)Nc1nc(N)c(-c2ccccc2)s1
2-(acetylamino)-4-amino-5-phenylthiazole
收率 23.1%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度heated
  2. 2
    温度to reflux for 3.5 hr
  3. 3
    浓缩The cooled mixture was concentrated in vacuo
  4. 4
    其他partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. 5
    洗涤The organic phase was washed with brine
  6. 6
    干燥dried over sodium sulfate
  7. 7
    过滤filtered
  8. 8
    浓缩concentrated in vacuo

实验过程

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%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08110568B2uspto-grants-2012_02