p-Toluenesulfonic acid → HCID 57814406, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 12.3 g (50 mmol) of 4-iodo-2,5-dimethylaniline and 83 ml (500 mmol) of triethoxymethane 0.48 g (2.50 mmol) of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 16 hrs and concentrated in vacuo. The crude product was dissolved in 100 ml of dichloromethane and 5.91 g (100 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at 40° C. The reaction mixture was concentrated in vacuo. Column chromatographie (cyclohexane/ethyl acetate 3:1) yielded 13.4 g (42.3 mmol) 85% of N′-(4-iodo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=1.21.

Provenance & Evidence