Trifluoroacetic acid → HCID 14500636, compound

Participants

Reaction Steps

1-Ethyl-2-(3'-aminobenzyl)pyrrole 5.6 g (28 mmol) was dissolved in a mixture of 500 ml of methylene chloride and 100 ml methanol; 3.92 g (60 mmol) of sodium cyanate were added to the solution and thereafter, in a dropwise fashion and at room temperature, 4.6 ml (59 mmol) of trifluoroacetic acid in 100 ml of methylene chloride. When the addition was completed, the resulting mixture was stirred for 72 hours, 10 g (90 mmol) of sodium carbonate were added thereto, the mixture stirred for 15 minutes and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel, using methylene chloride-acetone (85:15) as eluant, to produce 4.44 g (65%) of the title compound, 1-ethyl-2-(3'-ureidobenzyl)pyrrole, which was recrystallized from acetone-hexane.

Provenance & Evidence