Ethanol → 5-Isothiocyanato-2-(5-methylfuran-2-yl)-1,3-benzoxazole

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Reaction Steps

3.32 g (0.0013 mole) of 5-nitro-2-(5-methyl-2-furyl)-benzoxazole and 0.65 g of 10% Pd are suspended in 100 ml of abs. EtOH and hydrogenated at 65 psi over a period of 4 hr. The catalyst is removed and the EtOH evaporated under vacuum yielding a dark brown residue. The residue is dissolved in 150 ml of CHCl3 and added dropwise to the following cold suspension: 1.5 g (0.013 mole) of thiophosgene, 1.3 g (0.013 mole) of calcium carbonate, 150 ml of CHCl3 and 30 ml of water. After the addition is complete the mixture is warmed to room temperature and allowed to stir overnight. The CHCl3 layer is then separated and evaporated to dryness yielding 1.4 g of a light brown solid (43%) mp 110°-121°. This material is then extracted with petroleum ether and the extracts then evaporated yielding a tan solid. This material is recrystallized from petroleum ether yielding 0.540 g of white powder, mp 130°-132°(16%).

Provenance & Evidence