Toluene → HCID 21432645, compound

Participants

Reaction Steps

A 3000 ml 3-neck round bottom flask, equipped with a Dean-Stark water trap and a mechanical stirrer, was charged with 203.5 g (10% molar excess) of chlorendic anhydride and 1600 ml of toluene. Sixty-two grams of 2-mercaptoaniline was added to the resultant solution, whereupon a pale yellow suspension was formed. The reaction mixture was heated gradually until the solvent began to reflux and the evolution of water commenced and it was collected in the Dean-Stark water trap. The heating and refluxing were continued until the calculated amount of water, 9 ml. was collected, this requiring a total of 6 hours. At this point, there was no solid left in the reaction mixture. Solvent was then distilled to reduce the volume to about one-half. The residue, a clear solution, was then poured into 1000 ml of Skellysolve B (a mixture of hexanes, b. pt. = 146°-156° F., from Skelly Oil Co.) and the resultant solid was separated by filtration on a Buchner funnel and dried in air overnight. One crystallization from toluene gave white crystals of the dicarboximide with a melting point of 195°-8° C.

Provenance & Evidence