Dimethylhydantoin → HCID 68563813, compound

Participants

Reaction Steps

To a stirring solution of NaH (60% in mineral oil, 1.75 g) in DMF (25 mL) at 5° C. was added 5,5-dimethyl hydantoin (5 g, 39.0 mmol, 1 eq) and the reaction was stirred for 30 min. Added (2-bromoethyl)trimethylammonium (9.6 g, 39.0 mmol, 1 eq) at that temperature and the reaction was heated to 50° C., while stirring overnight. Reaction was cooled to room temperature and the product crashed out of solution as a white solid, which was cooled to 5° C., filtered and washed with cold DMF (30 mL). Purified by prep-HPLC (gradient from 5% to 95% MeOH in H2O; 20 mL/min flow rate; C18 Restek column) to yield the desired product. Yield: 778 mg (7%). 1H-NMR (400 MHz, D2O) δ 4.005 (t, J=7.6 Hz, 2H), 3.643 (t, J=7.6 Hz, 6H), 3.238 (s, 9H), 1.441 (s, 6H) LCMS—[M] m/z 214.05

Provenance & Evidence