4-Aminobenzoic Acid → 4-(methylcarbamoylamino)benzoic acid

Participants

Reaction Steps

A mixture of 3.0 g (0.22 mol) of 4-aminobenzoic acid (Aldrich) in 100 mL of chloroform was treated with 10 g (0.175 mol) of methylisocyanate (Aldrich), and the mixture was stirred at ambient temperatures for three days. The mixture was concentrated and the residue was triturated with diethyl ether/petroleum ether. The solid was collected by filtration, air-dried, and then slurried with 100 mL of water. The solid was collected by vacuum filtration and the cake was sucked dry. The cake was then recrystallized from acetonitrile/water to yield 1.8 g (43%) of the title compound as a fluffy white solid, mp>400° C. (lit1 mp>300° C.).

Provenance & Evidence