反应详情

温度

-40 °C

Potassium nitrate (583 mg, 5.77 mmol) was added to a solution of 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide (514 mg, 2.30 mmol) in MeCN (23 ml) at room temperature. The mixture was cooled to −40° C., and sulfuryl chloride (1.68 M solution in dichloromethane, 3.46 ml, 5.81 mmol) was then added dropwise over 15 minutes. After stirring at −40° C. to −20° C. for 2.5 hours, the reaction mixture was diluted with dichloromethane (80 ml) and quenched with a saturated aqueous sodium bicarbonate solution (20 ml). The organic layer and the aqueous layer were separated, and the organic layer was then washed with a saturated aqueous sodium chloride solution (30 ml), dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2) to give 2-(4-dimethylcarbamoyl-2-methyl-phenyl)-ethanesulfonyl chloride as a colorless solid (491 mg, 74%).

1. customquenched with a saturated aqueous sodium bicarbonate solution (20 ml)
2. customThe organic layer and the aqueous layer were separated
3. washthe organic layer was then washed with a saturated aqueous sodium chloride solution (30 ml)
4. dry with materialdried over MgSO4
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→1/2)