Реакция #1726701

Уравнение реакции

ammonia

hydrazine

sulfonyl chloride

4-phenyl-5-phthalimido-thiazole

hydrazine

→

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

Выход 36.0%

5-amino-4-phenylthiazole

Выход 16.0%

Растворители

methanol

dichloromethane

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter 10 min the mixture was concentrated in vacuo
2. 2
   Температураheated to reflux
3. 3
   Температураreflux
4. 4
   ФильтрацияThe cooled mixture was filtered
5. 5
   Концентрированиеconcentrated in vacuo

Методика

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).

Источник