Benzene → 4-(2,4-Dichlorobenzoyl)-1-methyl-5-(4-nitrobenzyloxy)-pyrazole

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Reaction Steps

To a mixture of 1.36 g (0.005 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, 0.51 g (0.005 mol) of triethylamine, 20 ml of benzene and 10 ml of N,N-dimethylformamide was added with stirring 0.86 g (0.005 mol) of 4-nitrobenzyl chloride at room temperature. The resulting mixture was then heated under reflux for 3 hours. After cooling the reaction mixture, the solvent was distilled off under reduced pressure and 30 ml of water and 30 ml of ethyl acetate were added thereto. After stirring the mixture for a while, an organic layer was separated, washed with water and 5% aqueous sodium bicarbonate and dried. Then the solvent was distilled off therefrom. The resulting oil (2.02 g) was subjected to column chromatography (silica gel, eluting with benzene/ethyl acetate 1:1) to give 1.76 g of the title compound (yield 87%), m.p. 116.5°-117.5° C.

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