Methacrylic Acid → N-(p-aminosulfonylphenyl)methacrylamide

Participants

Reaction Conditions

Reaction Steps

Into a 500 ml-volume three-necked flask equipped with a stirrer, a condenser tube and a dropping funnel were charged 31.0 g (0.36 mol) of methacrylic acid, 39.1 g (0.36 mol) of ethyl chloroformate and 200 ml of acetonitrile, and the resulting mixture was stirred under cooling in an ice water bath. To the mixture, 36.4 g (0.36 mol) of triethylamine was added dropwise through the dropping funnel over a period of about one hour. After the completion of the dropwise addition, the ice water bath was removed, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 51.7 g (0.30 mol) of p-aminobenzenesulfonamide, and the resulting mixture was stirred for one hour while heating to 70° C. on an oil bath. After the completion of the reaction, the reaction mixture was poured into one liter of water while stirring the water, and the resulting mixture was stirred for 30 minutes. The mixture was filtered to collect deposit and the deposit was made into a slurry with 500 ml of water. The slurry was filtered and the resulting solid was dried to obtain a white solid of N-(p-aminosulfonylphenyl)methacrylamide (yield: 46.9 g).

Provenance & Evidence