Acryloyl chloride → 1-Acryloyl-3,4-dimethyl-5-phenylimidazolidin-2-one

Participants

Reaction Steps

To a solution of (4 S, 5 R)1,5-dimethyl-4-phenyl-2-imidazolidinone (45.0 g, 237 mmole) and (i-Pr)2NEt (62 mL, 355 mmole) in CH2Cl2 (1200 mL) was added CuCl (50 mg, 0.51 mmole) then acryloyl chloride (29 mL, 355 mmole), and the mixture was heated to reflux. After 2 hr the mixture was cooled to RT, washed with H2O (3×400 mL), dried over MgSO4, and concentrated. The resulting solid was triturated with Et2O (300 mL) and collected by filtration to give the title compound (45.15 g, 78%): 1H NMR (300 MHz, CDCl3) δ 7.72 (dd, J=17.0, 10.5 Hz, 1 H), 7.20-7.38 (m, 3 H), 7.10-7.20 (m, 2 H), 6.40 (dd, J=17.0, 2.1 Hz, 1 H), 5.77 (dd, J=10.4, 2.0 Hz, 1 H), 5.36 (d, J=8.5 Hz, 1 H), 3.85-4.00 (m, 1 H), 2.85 (s, 3 H), 0.82 (d, J=6.6 Hz, 3 H); MS (ES) m/e 245 (M+H)+.

Provenance & Evidence