反応 #1726700

反応方程式

sodium thiosulfate

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

3-chloroperbenzoic acid

sodium bicarbonate

3-chloroperbenzoic acid

→

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

収率 26.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度to warm to ambient temperature
2. 2
   workup.ADDITION1.4 mmol) was added portionwise
3. 3
   抽出extracted three times into dichloromethane (total 100 ml)
4. 4
   洗浄The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to give a dark brown foam

実験手順

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%).

出典