Water → HCID 80021658, compound

Participants

Reaction Steps

To a cold (0° C.) solution of S-(2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)ethyl) ethanethioate (17 g, 74 mmol) prepared as described in International Patent Publication Number WO 2010/054009 A1 (Jain et al., Apr. 11, 2009), in 150 mL of methanol and 100 mL of water was added 22.5 mL of 5 N NaOH. The external ice bath was removed and the mixture was allowed to warm to room temperature, and stirred for 18 hours. Concentrated hydrochloric acid (8 mL) and 10 mL of water were added and the resultant solution was concentrated to about half of its original volume. White solid product precipitated out of solution and was collected on a glass fritted filter. The remaining aqueous solution was extracted with ethyl acetate, and the organic layer was then successively washed with water and sat. NaCl solutions. The organic fraction was dried over sodium sulfate and concentrated to a white solid, which was combined with the precipitated material to give the desired product (13.2 g, 70.2 mmol, 95%). 1H NMR (CDCl3, 400 MHz) δ 1.37-1.41 (t, J=8.5 Hz, 1H), 1.48 (s, 6H), 2.81-2.86 (m, 2H), 3.69-3.73 (t, J=7.0 Hz, 1H), 5.53 (br s, 1H); LRMS (ESI/APCI) m/z 189 [M+H]+.

Provenance & Evidence