Isopropenyl chloroformate → Prop-1-en-2-yl 2-phenyl-4-methylphenylcarbamate

Participants

Reaction Steps

To a biphasic solution of 2-phenyl-4-methylbenzenamine (0.29 g, 1.583 mmol) in EtOAc (10 mL) and NaHCO3 (10 ml) was added prop-1-en-2-yl carbonochloridate (0.259 ml, 2.374 mmol) and mixture was stirred for 16 h at RT. The layers were separated and the aqueous layer was extracted with EtOAc (1×30 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to provide prop-1-en-2-yl 2-phenyl-4-methylphenylcarbamate as an off-white solid (0.33 g, 78% yield). 1H NMR (400 MHz, CDCl3): δ 8.00 (brs, 1H), 7.50-7.46 (m, 2H), 7.42-7.35 (m, 3H), 7.18 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.05 (s, 1H), 6.67 (brs, 1H), 4.72 (s, 1H), 4.68 (s, 1H), 2.34 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 290.0 (M+Na+).

Provenance & Evidence