تفاعل #1383365

معادلة التفاعل

sodium thiosulfate

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

3-chloroperbenzoic acid

sodium bicarbonate

3-chloroperbenzoic acid

→

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

المردود 26.0%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to ambient temperature
2. 2
   workup.ADDITION1.4 mmol) was added portionwise
3. 3
   استخلاصextracted three times into dichloromethane (total 100 ml)
4. 4
   غسيلThe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىto give a dark brown foam

الإجراء التجريبي

To 5-amino-2-(methylsulfanyl)-4-phenylthiazole (302 mg, 1.36 mmol) in dichloromethane (5.0 ml) was added portionwise 3-chloroperbenzoic acid (638 mg, 77% wt, 2.9 mmol) with cooling to 0° C. The mixture was diluted with dichloromethane (3.0 ml) and after 5 min allowed to warm to ambient temperature. After 3 hr a further quantity of 3-chloroperbenzoic acid (305 mg, 77% wt, 1.4 mmol) was added portionwise. After 20 hr the mixture was treated with sodium thiosulfate (2 ml, 1.0 M), poured into saturated aqueous sodium bicarbonate and extracted three times into dichloromethane (total 100 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo to give a dark brown foam. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(methylsulfonyl)-4-phenylthiazole (90 mg, 26%).

المصدر