Ethyl Bromide → HCID 178510892, compound

Participants

Reaction Steps

2-cyanoethanethioamide (501 mg, 5.00 mmol) and bromoethane (448 μL, 6.00 mmol) were added an ethanolic solution of sodium ethoxide (6.00 mmol, 3 mL). The resulting mixture was stirred for 6 hours, 2-amino-5-chlorobenzoic acid (858 mg, 5.00 mmol) was added, and the reaction was refluxed overnight with stirring. A solid precipitate formed upon cooling of the reaction mixture, which was recovered by vacuum filtration and washed sequentially with ethanol, water, ethanol, and diethyl ether. The solid was then dried to yield 2-(6-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (314 mg, 29%). 1H NMR (500 MHz, DMSO-d6) δ ppm 4.18 (s, 2H), 7.70 (d, J=8.8 Hz, 1H), 7.85 (dd, J1=8.7 Hz, J2=2.0 Hz, 1H) 8.03 (d, J=2.4 Hz, 1H).

Provenance & Evidence