Methane → Etanidazole

Participants

Reaction Steps

A mixture of 2.50 g (13.5 mmol) of methyl 2-nitroimidazole-1-acetate and 3.0 ml (50.0 mmol) of ethanolamine in 15.0 ml methanol was stirred 20 hr at room temperature. The mixture was diluted with 45 ml ethanol and heated on a stream bath to effect solution. The hot solution was decolorized with charcoal, filtered and evaporated to dryness. The residue was recrystallized from a solution of 150 ml ethyl acetate and 10 ml of methanol to afford 1.81 g (62.4%) of SR-2508 as a white powder, mp 164.5-165.0° C., that was homogeneous by thin layer chromatography on silica gel with 10% methanol in ethyl acetate (Rf 0.16). The solubility of SR-2508 in 0.9% saline solution was approximately 200 mg/ml.

Provenance & Evidence