2,5-Dimethylaniline → n-(2,5-Dimethylphenyl)-n-{4-[2-(4-fluorophenyl)-2-oxoethyl]phenyl}urea

Participants

Reaction Steps

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (0.100 g, 0.387 mmol) in acetonitrile was added proton sponge ((0.083 g) and diphenylphosphoryl azide (0.106 g). The reaction mixture was refluxed for 30 minutes. 2,5-dimethyl aniline (0.047 g, 0.388 mmol) was added and the mixture was refluxed another 30 minutes. The reaction was quenched with HCl 1 M and extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified using flash chromatography eluting with hexane/ethyl acetate 40% to give (0.052 g) of the title compound.

Provenance & Evidence