Dimethylhydantoin → 3-(2-Chloroethyl)-5,5-dimethylimidazolidine-2,4-dione

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Reaction Steps

5,5-Dimethylhydantoin (5 g, 39 mmol, 1 eq.) was added to a solution of potassium hydroxide (2.18 g, 39 mmol, 1 eq.) in EtOH (100 mL). 1-bromo-2-chloroethane (11.2 g, 78 mmol, 2 eq.) was added in one portion. The resulting mixture was refluxed overnight. Reaction was cooled to room temperature and concentrated in vacuo. Crude residue was re-suspended in ethyl acetate (150 mL), and washed with H2O (100 mL), saturated aqueous sodium bicarbonate (100 mL) then brine (100 mL). Organic layer was dried (Na2SO4) and concentrated in vacuo to yield the crude product, which was directly used in the next step. Yield: 5.4 g (73%). LCMS—[M+H] m/z 191.

Provenance & Evidence