3-methyl-1,3-oxazolidin-2-one

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of aniline hydrochloride (13.0 g, 0.10 mole), 3-methyl-2-oxazolidinone (11.0 g, 0.109 mole) and 35 ml of 2-(2-methoxyethoxy)ethanol was heated to 170° C. in an oil bath. The reaction mixture became homogenous and carbon dioxide evolution occurred on heating. After 17 hours, the reaction was allowed to cool to room temperature. After a workup procedure similar to that described in Example 1 and distillation at 105° C. to 110° C. (0.4 mm), an 81 percent distilled yield of the product was obtained as a clear liquid. Product confirmation was made by the use of spectra evidence. on heating to cool to room temperature After a workup procedure similar to that described in Example 1 and distillation at 105° C. to 110° C. (0.4 mm) an 81 percent distilled yield of the product was obtained as a clear liquid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-methyloxazolidin-2-one, 2.02 g (0.02 mole), in dry methylene chloride under dry nitrogen is added 2.28 g (0.02 mole) of methyl fluorosulfonate in one portion. After stirring 3 hrs, 0.02 mole of N-phenyl-1-pyrrolidinecarboximidamide free base in dry methylene chloride is added. After stirring at room temperature overnight, the solution is shaken with excess cold 3 N NaOH. The organic layer is separated and dried over K2CO3, filtered, and the solvent removed in vacuo to afford the crude base. Addition of an equimolar amount of fumaric acid to a solution of the free base in isopropanol, followed by recrystallization from isopropanol/ether affords pure N-(3-methyl-2-oxazolidinylidene)-N'-phenyl-1-pyrrolidinecarboximidamide fumarate; m.p. 160°-162° C. After stirring at room temperature overnight The organic layer is separated dried over K2CO3 filtered the solvent removed in vacuo to afford the crude base followed by recrystallization from isopropanol/ether