Sodium Azide → 4-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

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Reaction Steps

20.0 g (0.47 mol) of lithium chloride and 20.5 g (0.315 mol) of sodium azide are added to 41.2 g (0.315 mol) of 4-cyano-benzaldehyde (Fluka, Buchs, Switzerland) in 310 ml of methoxyethanol (Fluka, Buchs, Switzerland) and the mixture is heated at boiling for 6 hours (argon atmosphere). The cooled reaction mixture is poured into 1 liter of ice/37% HCl 10:1 and stirred thoroughly to complete the reaction. Filtration and washing with water yield the title compound: m.p.: 180-182° C.; 1H-NMR (DMSO-d6) δ 10.11 (s, HCO), 8.29 and 8.14 (2d, J=8, each 2H).

Provenance & Evidence