Dimethylhydantoin → 3-(2-(2-(2-Methoxyethoxy)ethoxy)ethyl)-5,5-dimethylimidazolidine-2,4-dione

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Reaction Steps

5,5-Dimethylhydantoin (1.32 g, 10.3 mmol) was dissolved in N,N-dimethylformamide (100 ml). To the stirring room temperature solution was added sodium hydride (60%, 412 mg, 10.2 mmol). After an additional one hour of stirring at room temperature, [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]p-toluenesulfonate (3.28 g, 10.3 mmol) was slowly added to the basic solution over a 20 minute period. The reaction mixture was stirred for an additional 18 hours at room temperature. The reaction mixture was concentrated under high vacuum. The solid material was dissolved in dichloromethane and the solution was filtered to remove any solid material. The organic layer was concentrated in vacuo, and crude material was purified by preparative-high pressure liquid chromatography to give 900 mg (31%) of the title compound. 1H NMR (D2O, 400 MHz) δ 3.56-3.51 (m, 12H), 3.37 (s, 3H), 1.42 (s, 6H); LRMS (ESI/APCI) m/z 275 [M+H]+.

Provenance & Evidence