Ethanol → Ethyl 2-isopropyl-5-oxo-1-imidazolidineacetate

Participants

Reaction Conditions

Reaction Steps

To 50 ml of anhydrous ethanol stirred at 0°-5° C., 2 ml thionyl chloride were added. At the same temperature 2.1 g (0.01 mol) of sodium 2-(1-methylethyl)-5-oxo-1-imidazolidineacetate were added. The obtained suspension was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the residue taken up with ethyl acetate. The solid residue was filtered off and the solvent evaporated. The residue was dissolved in a saturated solution of sodium hydrogen carbonate and extracted with 3×50 ml of dichloromethane. The organic layers were evaporated to give ethyl 2-(1-methylethyl)-5-oxo-1-imidazolidineacetate (0.9 g) as a pale-yellow oil (42%) (Rf 0.6, ethyl acetate/dichloromethane 6:4; silica gel plates). Hydrochloride salt, m.p. 148°-149° C. (methanol/ethyl acetate).

Provenance & Evidence