Water → HCID 21327522, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3.2 g of 4-phenyl-6-nitro-2(1H)-quinazolinone in 50 ml of dimethylformamide was added 0.7 g of 50% sodium hydride, and the mixture was stirred at 50° C. for 1 hour. Then, 3.96 g of tetrahydrofurfuryl bromide was added thereto and the resultant mixture was stirred at 100° C. for 7 hours. After cooling, the reaction mixture was poured into 300 ml of water and the resultant mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give red oily residue. The residue was chromatographed on silica gel using chloroform as eluting solvent to obtain 1.9 g of 1-tetrahydrofurfuryl-4-phenyl-6-nitro-2(1H)-quinazolinone and 0.6 g of 2-tetrahydrofurfuryloxy-4-phenyl-6-nitroquinazoline. Each of them was recrystallized from ethanol, and the former gave pale yellow prisms, m.p. 151°-153° C. and the latter gave pale yellow scales, m.p. 135°-137° C.

Provenance & Evidence