Cyclohexanecarbonyl chloride → 2-Cyclohexyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole

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Reaction Steps

A mixture of 5-(4-nitro-phenyl)-1H-tetrazole (0.5 g, 2.62 mmol) and cyclohexane carbonyl chloride (0.35 ml, 2.62 mmol) in 3 ml anhydrous pyridine was stirred at room temperature under nitrogen for 20 min, then heated to 60° C. for 1 hr and finally heated to 100° C. for 2 h. The reaction mixture was cooled to room temperature then poured onto ice (30 g) and the aqueous mixture was extracted with 30 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 30 ml water, 30 ml 1N aqueous hydrochloric acid solution and 30 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The crude produce was purified by flash column chromatography (silica gel, 40 g), eluting with 4:1 hexane/ethyl acetate to yield the title compound as a yellowish solid (0.5 g, 100% yield). MS: 274.2 (M+1)

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