p-Toluenesulfonic acid → N-(3-Phenylsalicylidene)-4-iodoaniline

Participants

Reaction Steps

An amount of 20.6 mmol of 3-phenyl salicylaldehyde (2) (4.08 g) was dissolved in 150 ml of toluene. After addition of 4-iodoaniline (5.42 g/24.8 mmol) and a few crystals of para-toluenesulfonic acid, the reaction mixture was stirred under reflux for three hours applying a Dean-Stark-trap. After cooling down to room temperature, sodium hydrogencarbonate solution (150 ml) was added. The organic phase was separated and filtered over sodium sulfate and silica. Removing the solvent and recrystallization from ethanol at −20° C. gave the title compound as a red solid. Yield: 7.25 g (88%).

Provenance & Evidence