p-Toluenesulfonic acid → N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide

Participants

Reaction Steps

To a mixture of 10.0 g (50 mmol) of 4-bromo-2,5-dimethylaniline and 126 ml (1.15 mol) of trimethoxymethane 0.86 g (5 mmol) of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 16 hrs and concentrated in vacuo. The crude product was solved in 50 ml of dichloro methane and 5.9 g (100 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at room temperature. The reaction mixture was concentrated in vacuo. Column chromatographic (gradient: petroleum ether->methyl-tert.butyl ether) yielded 5.2 g (19.5 mmol) 39% of N′-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=1.36.

Provenance & Evidence