ETANIDAZOLE synthesis

Yield: 1.81 g (62.4%)

Reaction Conditions:

in methanol;ethanol;ethyl acetate

Steps:

1 Preparation of N-(2-hydroxyethyl)-2-(2-nitro-1-imidazolyl)acetamide (SR-2508)
The product was very soluble in ethanol and was soluble in 0.9% saline to the extent of 13.6 mg/ml. 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 (R_f 0.16).

References:

The United States of America as represented by the Secretary of the Department of Health and Human Services US4371540, 1983, A