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N,N-Dimethylaniline (8 ml) was dissolved in 20 ml of chloroform, and chlorosulfonic acid (20 ml) was slowly added with cooling. The reaction mixture was refluxed for 6 hr. The reaction mixture was cooled and poured on ice (100 g). Dichloromethane (120 ml) was added and aqueous layer was neutralized by concentrated sodium carbonate solution with keeping temperature below 4 ° C. Organic layer was again washed with ice-cold 0.1N sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. Organic layer was concentrated under reduced pressure. Residual material was crystallized from ethyl ether-heptane to give yellowish green solid. p-(Dimethylamino)benzenesulfonyl chloride (4.2 g) was obtained. M. P. 108-13 111° C.

1. temperaturewith cooling
2. temperatureThe reaction mixture was refluxed for 6 hr
3. temperatureThe reaction mixture was cooled
4. additionpoured on ice (100 g)
5. customtemperature below 4 ° C
6. washOrganic layer was again washed with ice-cold 0.1N sodium bicarbonate solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationOrganic layer was concentrated under reduced pressure
9. customResidual material was crystallized from ethyl ether-heptane
10. customto give yellowish green solid