تفاعل #1726701

معادلة التفاعل

ammonia

hydrazine

sulfonyl chloride

4-phenyl-5-phthalimido-thiazole

hydrazine

→

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

المردود 36.0%

5-amino-4-phenylthiazole

المردود 16.0%

المذيبات

methanol

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   تركيزAfter 10 min the mixture was concentrated in vacuo
2. 2
   درجة الحرارةheated to reflux
3. 3
   درجة الحرارةreflux
4. 4
   ترشيحThe cooled mixture was filtered
5. 5
   تركيزconcentrated in vacuo

الإجراء التجريبي

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).

المصدر