Triethylamine → HCID 178511153, compound

Participants

Reaction Steps

To solution of 2-(5-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (26.4 mg, 120 μmol) and triethylamine (18.4 μL, 132 μmol) in dioxane (4 mL) was added 2,4-dichlorobenzoyl chloride (18.5 μL, 132 μmol), 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 B (3) (12.8 mg, 27%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.46 (dd, J1=7.5 Hz, J2=1.4 Hz, 1H), 7.50 (d, J=8.2 Hz, 1H), 7.55 (dd. J1=8.2 Hz, J2=1.9 Hz, 1H), 7.68-7.79 (m, 3H). 13C NMR (500 MHz, DMSO-d6) δ ppm 71.69, 114.6, 117.63, 118.45, 127.65, 128.1, 129.2, 129.65, 130.49, 133.35, 134.8, 135.47, 138.2, 154.81, 156.48, 188.71. HRMS (m/z): [M+Na]+ calc. for C17H8N3O2Cl3Na, 413.9580; observed, 413.9582.

Provenance & Evidence