Triethyl orthoacetate → 2-Methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole

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Reaction Steps

A mixture of 3-nitro-5-(trifluoromethyl)benzohydrazide (20 g, 80 mmol) in 1,1,1-triethoxyethane (156 g, 963 mmol) was heated to reflux and stirred for 12 h. Then the solvent was concentrated to yield a black solid of 2-methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole (20 g, 65.9 mmol, 82% yield): 1H NMR (400 MHz, CD3OD) δ 9.04 (s, 1H), 8.71 (s, 1H), 8.66 (s, 1H), 2.67 (s, 1H); ES-LCMS m/z 274 (M+H).

Provenance & Evidence