Ethanol → 5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

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Reaction Steps

NaBH4 (8.2 g, 0.22 mol) is added portionwise slowly to EtOH (700 mL) solution of crude 2-methyl-N-[3,5-bis(trifluoromethyl)phenylmethylene]-2H-tetrazole-5-amine at 0° C., and the mixture is stirred at room temperature for 1 hour. After addition of sat. NH4Cl aq. and water at 0° C., the mixture is concentrated to remove 300 mL of EtOH and extracted with CH2Cl2 (300 mL×4 times). The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated The residue is purified by silica gel column chromatography to give N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amine as a white crystalline solid.

Provenance & Evidence