Trifluoroacetic acid → HCID 14500646, compound

Participants

Reaction Steps

A solution of 3.5 ml (45 mmol) of trifluoroacetic acid in 25 ml of benzene was added dropwise to a suspension of 5 g (21 mmol) of 1-butyl-2-(3'-aminobenzyl)pyrrole and 2.85 g (43 mmol) of sodium cyanate in 250 ml of benzene. The reaction mixture was stirred at room temperature for 1 hour further and then poured into 600 ml of saturated sodium carbonate solution. The organic phase was separated and the aqueous phase extracted with ethyl acetate (3×300 ml). The combined extracts were washed with water (2×250 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using hexane-ethyl acetate (30:70) as eluant, thus obtaining 3.82 g (65%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Provenance & Evidence