5-Methylfurfural → 2-(5-Methylfuran-2-yl)-5-nitro-1,3-benzoxazole

Participants

Reaction Steps

7.70 g (0.05 mole) of 4-nitro-2-aminophenol and 5.50 g (0.05 mole) of 5-methylfurfural are dissolved in 400 ml of 95% EtOH and refluxed overnight. The ethanol is removed and the resulting dark red oil is recrystallized from CH3CN yielding golden plates of the Schiff Base, mp 190°-193°. This material is then dissolved in CH3CN (200 ml) by heating and 22.2 g (0.05 mole) of lead tetraacetate added. Heating is continued for 5 min and then solution is diluted with an equal volume of water. The dark brown precipitate is collected, washed with water and recrystallized from CH2Cl2 and Darco G-60 yielding 6.1 g of product (50%), mp 182°-184°.

Provenance & Evidence