M-Phenylenediamine → N,N'-(m-phenylene)bis citraconamic acid

Participants

Reaction Steps

A 3-liter, 3-neck round bottom flask was charged with 54 g (0.5 mole) of m-phenylenediamine and 500 ml of reagent acetone and flushed with nitrogen. The flask was fitted with a reflux condenser, mechanical stirrer and thermocouple. The solution was stirred as 112 g (1.0 mole) of citraconic anhydride in 500 ml of reagent acetone was added dropwise over about 11/2 hours as the temperature was allowed to rise to reflux the acetone. The reaction mixture was refluxed for an additional hour, cooled to room temperature and suction filtered to give 166 g of N,N'-(m-phenylene)bis citraconamic acid as shown by NMR analysis, as a tan mustard-colored solid melting at 152°-156° C.

Provenance & Evidence