Dimethylamine → HCID 13078516, compound

Participants

Reaction Steps

To 15 ml (0.227 mole) of chlorosulfonic acid was added 10.0 g (0.0403 mole) of 1-(4-(methylsulfonyl)phenoxy)benzene in small portions keeping the temperature below 55° C. After the addition was complete and the mixture had stirred at ambient temperature for 10 minutes, the mixture was slowly poured over ice and water. The crystalline 4-(4-(methylsulfonyl)phenoxy)benzenesulfonyl chloride was collected by filtration, washed with water and dried. The material was dissolved in 350 ml of CH2Cl2 and 26.6 g (0.177 mole) of 30% aqueous dimethylamine was added dropwise. The reaction mixture was heated at reflux temperature for 1.5 hrs and cooled. The mixture was extracted with 3N aqueous hydrogen chloride, dried (Na2SO4) and solvent removed in vacuo, which gave 13.4 g (93.7% yield) of product. Recrystallization from ethanol, followed by purification using column chromatography with silica gel as the support and chloroform as the eluent gave purified N,N-dimethyl-4-(4-(methylsulfonyl)phenoxy)benzenesulfonamide, mp 127.5°-130° C.

Provenance & Evidence