Sodium Azide → 2-(Azidomethyl)-5-methyl-1,3,4-oxadiazole

Participants

Reaction Steps

A solution of 2-(chloromethyl)-5-methyl-1,3,4-oxadiazole (R. Rufenacht, Helv. Chim. Acta, 55, 1979, 1972) (2.00 g, 15.09 mmol) in N,N-dimethylformamide (75 ml) was treated at 22° C. with sodium azide (3.0 g, 46.1 mmol) and the resulting mixture was stirred for 18 h. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by chromatography of the residue on silica gel (elution toluene-ethyl acetate 0-10%) gave 1.78 g (84% yield) of the title azide as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.60 (3H, s, CH3), 4.55 (2H, s, CH2). MS (ESI+) m/e 140 [M+H+].

Provenance & Evidence