Aniline → N-Phenyltetrachlorophthalimide

Participants

Reaction Conditions

Reaction Steps

Tetrachlorophthalic anhydride (300 g, 1.05 moles) was combined with aniline (100 g, 1.08 moles) and glacial acetic acid (3750 ml) in a 3-neck round bottom flask fitted with a cold-water condenser, overhead stirrer and a thermometer. The mixture was allowed to reflux (114° C.) with stirring for 6.5 hours. Crystallization occurred upon cooling. The crystals were filtered, washed with cold water and dried at 120° C., 0.5 mm Hg for 18 hours. 366 g tetrachloro-N-phenylphthalimide (96% yield) were recovered, mp 274°-275° C. The product was identified by gc/ms.

Provenance & Evidence