Trifluoroacetic acid → HCID 14500631, compound

Participants

Reaction Steps

To a stirred solution of 4.4 g (23 mmol) of 1-methyl-2-(3'-aminobenzyl)pyrrole in 400 ml of benzene there were added 3.08 g (47 mmol) of sodium cyanate followed by the dropwise addition of a solution of 3.65 ml (47 mmol) of trifluoroacetic acid in 300 ml of benzene. When the addition was completed, the reaction mixture was stirred at room temperature for 1 hour further and then poured into 500 ml of saturated sodium carbonate solution. The organic phase was separated and the aqueous layer extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (1×500 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 500 g of silica gel, using methylene chloride-acetone (80:20) as eluant, thus obtaining 5.1 g (90%) of the title compound, 1-methyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Provenance & Evidence