Guanidine Hydrochloride → HCID 9818000, compound

Participants

Reaction Steps

28% Methanolic sodium methoxide (6.2 ml) was added to a solution of guanidine hydrochloride (3.2 g) in dry methanol (40.0 ml) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate (1.9 g) and the mixture was stirred for 7 hours at the same temperature. The solvent was removed by concentration and the residue was added to a mixture of ethyl acetate, tetrahydrofuran and water. The separated organic layer was washed with brine and dried over magnesium sulfate. The residue was obtained by evaporating a solvent, and purified by column chromatography on alumina eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and diisopropyl ether to give 2-[3-methylsulfonyl-5-(pyrrol-1-yl)benzoyl]guanidine (0.44 g).

Provenance & Evidence