Triethylamine → 4-(Azidomethyl)-1-methyl-1H-1,2,3-triazole

Participants

Reaction Steps

A solution of (1-methyl-1H-1,2,3-triazol-4-yl)methanol (0.62 g, 5.48 mmol) (F. Sternfeld et al. J. Med. Chem. 47, 2004, 216-2179) in tetrahydrofuran (12 ml) was cooled to 0° C. and treated with methanesulfonyl chloride (0.42 ml, 5.50 mmol). Triethylamine (0.75 ml, 5.5 mmol) was then added dropwise and the mixture was stirred for 15 min. The reaction mixture was then diluted with N,N-dimethylformamide (10 ml), treated with sodium azide (0.80 g, 12.3 mmol) and stirred at 22° C. for 18 h. The mixture was then diluted with ethyl acetate washed with water and brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution ethyl acetate) gave 0.710 g (94% yield) of the title material as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 4.15 (3H, s, CH3), 4.51 (2H, s, NCH2), 7.57 (1H, s, CH). MS (ESI+) m/z 139 [M+H+].

Provenance & Evidence