2,4,5-Trichloronitrobenzene → 2-Methyl-4[4,5-dichloro-2-nitroanilino]-1,2,3-triazole-5-carbonitrile

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Reaction Steps

To a solution of 4-amino-2-methyl-1,2,3-triazole-5-carbonitrile (1.7 g) in tetrahydrofuran (40 ml) under nitrogen was added sodium hydride (1.0 g, 50% oil dispersion) at room temperature. After 15 minutes, 2,4,5-trichloronitro-benzene (3.13 g) was added to the mixture, which was stirred for six hours under nitrogen. The deep-red solution was then quenched in ice/water/HCl and filtered to leave a yellow-orange solid. The solid was chromatographed on a magnesium silicate column using dichloromethane. The purified product was recrystallised from ethanol to give an orange crystalline solid, melting point 148°-150° C.

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