Triethylamine → HCID 178511150, compound

Participants

Reaction Steps

To solution of 2-(4-oxo-1.4-dihydroquinazolin-2-yl)acetonitrile (202 mg, 1.09 mmol) and triethylamine (167 μL, 1.20 mmol) in dioxane (8 mL) was added 2.4-dichlorobenzoyl chloride (152 μL, 1.09 mmol), and the resulting mixture 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 methanol, water, methanol, and dichloromethane. The solid was then dried to yield ciliobrevin A (1) (213 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.46-7.50 (m, 1H), 7.52 (d. 1=8.2 Hz, 1H), 7.56 (dd, J1=8.2, J2=1.9 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.83-7.88 (m, 2H), 8.07 (d, J=8.1 Hz, 1H). 13C NMR (500 MHz, DMSO-d6) δ ppm 71.74, 117.43, 117.54, 118.71, 125.92, 126.68, 127.66, 129.21, 129.66, 130.49, 134.85, 135.85, 138.15, 139.25, 155.01, 158.3, 188.75. HRMS (m/z): [M+ calc. for C17H9N3O2Cl2Na, 379.9970; observed, 379.9967.

Provenance & Evidence