Trifluoroacetic acid → HCID 14500626, compound

Participants

Reaction Steps

A stirred solution of 3.1 g (12 mmol) of 1-butyl-2-(3'-aminobenzyl)-5-ethylpyrrole in 250 ml of dry methylene chloride and 50 ml of anhydrous methanol was treated, at room temperature and under nitrogen atmosphere, with 1.7 g (26 mmol) of sodium cyanate, followed by the dropwise addition, over a 2 hour period, of 2.3 ml (29 mmol) of trifluoroacetic acid in 100 ml of methylene chloride. The reaction mixture was stirred at room temperature for 18 additional hours, 2 g (18 mmol) of sodium carbonate were then added and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using methylene chloride-methanol (97:3) as eluant, thus obtaining 3.4 g (93%) of the title compound, 1-butyl-2-(3'-ureidobenzyl)-5-ethylpyrrole, which was recrystallized from ether-hexane.

Provenance & Evidence