Reacción #1726701

Ecuación de reacción

ammonia

hydrazine

sulfonyl chloride

4-phenyl-5-phthalimido-thiazole

hydrazine

→

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

Rendimiento 36.0%

5-amino-4-phenylthiazole

Rendimiento 16.0%

Disolventes

methanol

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter 10 min the mixture was concentrated in vacuo
2. 2
   Temperaturaheated to reflux
3. 3
   Temperaturareflux
4. 4
   FiltraciónThe cooled mixture was filtered
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

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).

Fuente