Реакция #1726700

Уравнение реакции

sodium thiosulfate

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

3-chloroperbenzoic acid

sodium bicarbonate

3-chloroperbenzoic acid

→

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

Выход 26.0%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураto warm to ambient temperature
2. 2
   workup.ADDITION1.4 mmol) was added portionwise
3. 3
   Экстракцияextracted three times into dichloromethane (total 100 ml)
4. 4
   ПромывкаThe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеto give a dark brown foam

Методика

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%).

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