Water → HCID 13207875, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 11 g of 4-phenyl-6-nitro-2(1H)-quinazolinone in 100 ml of dimethylformamide, was added 2.2 g of 52.9% sodium hydride. After stirring at 50°C for 1 hour, 17 g of 2-bromomethyl norbornane was added and the reaction mixture was heated under reflux for 8 hours. After cooling, the mixture was poured into 1l of water and the resulting mixture was extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residual oil was chromatographed on silica gel using chloroform as eluting solvent to obtain 1-(2-norbornylmethyl)-4-phenyl-6-nitro-2(1H)-quinazolinone and 2-(2-norbornylmethoxy)-4-phenyl-6-nitroquinazoline. The former was recrystallized from a mixture of carbon tetrachloride and diethyl ether, to give yellow needles, m.p. 160°- 161°C, and the latter was recrystallized from methylchloroform, to give yellow needles, m.p. 153°- 155°C.

Provenance & Evidence