2-Bromo-4'-methylacetophenone → HCID 86696592, compound

Participants

Reaction Steps

A suspension of N-(pyrrolidin-2-ylidene)cyanamide (1.09 g; 10 mmol) in acetonitrile (20 mL) was heated gently until dissolution and then potassium hydrogenocarbonate (1.66 g; 12 mmol) and 2-bromo-1-p-tolylethanone (2.98 g; 14 mmol) were added. The well stirred mixture was heated at reflux for 21 h and an extra amount of 2-bromo-1-p-tolylethanone (0.426 g; 2 mmol) was added. The reaction mixture was heated for 6 additional hours. After cooling, the precipitate was filtered, washed with dichloromethane and the filtrate was concentrated under reduced pressure. The crude residue was purified by flash-chromatography on silica gel using a gradient of ethyl acetate (1-20%) in dichloromethane to furnish 2.02 g (84%) of N-(1-(2-oxo-2-p-tolylethyl)pyrrolidin-2-ylidene)cyanamide as an orange solid. ESI/APCI(+): 242 (M+H). 1H NMR (CDI3) δ 7.83 (d, J=8.22 Hz, 2H, Harom.); 7.29 (d, J=8.04 Hz, 2H, Harom.); 4.81 (s, 2H, COCH2); 3.69 (m, 2H, CH2); 3.03 (m, 2H, CH2); 2.43 (s, 3H, CH3); 2.24 (m, 2H, CH2).

Provenance & Evidence