反応 #1726701

反応方程式

ammonia

hydrazine

sulfonyl chloride

4-phenyl-5-phthalimido-thiazole

hydrazine

→

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

収率 36.0%

5-amino-4-phenylthiazole

収率 16.0%

溶媒

methanol

dichloromethane

反応条件

後処理

1. 1
   濃縮After 10 min the mixture was concentrated in vacuo
2. 2
   温度heated to reflux
3. 3
   温度reflux
4. 4
   ろ過The cooled mixture was filtered
5. 5
   濃縮concentrated in vacuo

実験手順

The crude mixture of sulfonyl chloride with 4-phenyl-5-phthalimido-thiazole (231 mg) in dichloromethane (10 ml) was treated with ammonia in methanol (900 μl, 2.0 M) dropwise at ambient temperature. After 10 min the mixture was concentrated in vacuo. The residue was suspended in ethanol (10 ml), treated with ethanolic hydrazine (660 μl, 1.0 M, 660 μmol) and heated to reflux. After 1.5 hr a further portion of ethanolic hydrazine was added (660 μl, 1.0 M, 660 mol) and reflux continued for 15 hr. The cooled mixture was filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(aminosulfonyl)-4-phenylthiazole (56 mg, 36% for 3 steps) and 5-amino-4-phenylthiazole (17 mg, 16% for 3 steps).

出典