Reacción #1726700

Ecuación de reacción

sodium thiosulfate

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

3-chloroperbenzoic acid

sodium bicarbonate

3-chloroperbenzoic acid

→

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

Rendimiento 26.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente