Trifluoroacetic acid → HCID 14500618, compound

Participants

Reaction Steps

A solution of 3.5 ml (39 mmol) of trifluoroacetic acid in 200 ml of methylene chloride was added dropwise, over a 2 hour period and under nitrogen atmosphere, to a stirred suspension of 4.8 g (19 mmol) of 1-propyl-2-(3'-aminobenzyl)-5-ethylpyrrole and 2.58 g (39 mmol) of sodium cyanate in 400 ml of anhydrous methylene chloride and 90 ml of methanol. The reaction mixture was stirred at room temperature for 18 additional hours, 2 g (18 mmol) of sodium carbonate were added and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using hexane-acetone (1:1) as eluant, obtaining 4.04 g (72%) of the title compound, 1-propyl-2-(3'-ureidobenzyl)-5-ethylpyrrole, which was recrystallized from ether-hexane. M.P. 116°-118° C.

Provenance & Evidence