Sulfanilamide → N-(p-aminosulfonylphenyl)methacrylamide

Participants

Reaction Conditions

Reaction Steps

170.2 g (1.0 mole) of p-aminobenzenesulfonamide and 700 ml of tetrahydrofuran were placed in one liter three-necked flask equipped with a stirrer, a cooling coil and a dropping funnel and stirred in an ice-water bath. 52.3 g (0.5 mole) of methacrylic acid chloride was added dropwise from the dropping funnel to the mixture over a period of about one hour. After the completion of dropping, the ice-water bath was removed and the mixture was stirred at room temperature for 30 minutes and then stirred further for one hour while heating it in an oil bath at 60° C. After the completion of the reaction, the reaction mixture was introduced into 3 l of water with stirring, stirred for 30 minutes and filtered to obtain N-(p-aminosulfonylphenyl)methacrylamide as a white solid. The white solid was purified by recrystallizing it from a mixed solvent of water-acetone (yield: 39.3 g).

Provenance & Evidence