Methyl iodide → 4-(2-Methyl-2H-tetrazol-5-yl)-benzaldehyde

Participants

Reaction Steps

With ice-cooling, a solution of 75.5 g (0.434 mol) of 4-(tetrazol-5-yl)-benzaldehyde (Example 25a) in 550 ml of DMF/dioxane 1:1 is added dropwise to 179.7 g (1.30 mol) of K2CO3 in 200 ml of DMF/dioxane 1:1; the mixture is stirred for 30 min and then 40 ml (0.64 mol) of methyl iodide are added. The mixture is stirred in an ice bath for 3 hours and, finally, at room temperature for 15 hours; the reaction mixture is poured into 2.8 liters of ice-water and stirred for 10 min; the title compound is filtered off and washed with water: m.p.: 137-139° C.; 1H-NMR (CD3OD/CDCl3) d 10.05 (s, HCO), 8.29 and 8.03 (2d, J=8, each 2H), 4.43 (s, 3H).

Provenance & Evidence