Styrene → HCID 16719385, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl carbamate (1.0 g, 8.54 mmol) and 2-butenoyl chloride (2.4 mL, 25.0 mmol) was added styrene (30 mL), followed by CuCl (0.1 g). The reaction mixture was stirred at 114° C. for 16 h. It was then cooled to room temperature and evaporated to give a white residue, which was dissolved in DCM and washed with water, brine and dried over MgSO4. The solution was concentrated and the addition of pentane to the residue furnished the product as a white precipitate. Yield 76% (0.93 g). m.pt. 149–150° C. 1H NMR: δ 1.94 (dd, 1H, CH3CH, 2JHH=6.8 Hz, 3JHH=1.4 Hz); 3.78 (s, 3H, OCH3); 6.84 (dd, 1H, COCH, 2JHH=15.0 Hz, 3JHH=1.3 Hz); 7.10–7.20 (m, 1H, CH3CH); 7.89 (s, br, 1H, NH). 13C NMR: δ 18.4 (CH3CH), 53.0 (OCH3), 122.7 (COCH), 146.6 (CH3CH), 152.4 (CO2), 166.1 (COCH). m/z (HR-EIMS) Expected 143.0582 (M+), observed 143.0577. Anal. calcd for C9H9NO3: C, 50.35; H, 6.34; N, 9.79%. Found: C, 50.44; H, 6.59; N, 9.94%.

Provenance & Evidence