反应详情

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 3 N 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.

1. customthe temperature below 55° C
2. additionAfter the addition
3. filtrationThe crystalline 4-(4-(methylsulfonyl)phenoxy)benzenesulfonyl chloride was collected by filtration
4. washwashed with water
5. customdried
6. dissolutionThe material was dissolved in 350 ml of CH2Cl2
7. temperatureThe reaction mixture was heated
8. temperatureat reflux temperature for 1.5 hrs
9. temperaturecooled
10. extractionThe mixture was extracted with 3 N aqueous hydrogen chloride
11. dry with materialdried (Na2SO4) and solvent
12. customremoved in vacuo, which