Triethylamine → HCID 53866493, compound

Participants

Reaction Steps

A mixture of methyl 2-amidino-2-ethoxyiminoacetate hydrochloride (syn isomer) (2.1 g), 2-chloroacrylonitrile (875 mg) and triethylamine (2.0 g) in ethanol (21 ml) was stirred for 8 hours at ambient temperature and allowed to stand at the same temperature overnight. The mixture was evaporated to dryness and the residue was dissolved in a mixture of ethyl acetate (20 ml) and water (10 ml). The organic layer was separated out, treated with activated charcoal and evaporated to dryness. The residue was purified by a column chromatography on silica gel (30 g) using ethyl acetate-benzene (1:1) as an eluant to give a mixture (1.0 g) of methyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) and ethyl 2-ethoxyimino-2-(4-aminopyrimidin-2-yl)acetate (syn isomer) (1:1). mp 105° to 110° C.

Provenance & Evidence