Sodium Azide → 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (9.9 g, 0.0416 mol) in dry DMSO (90 mL) was added with stirring NaN3 (5.4 g, 0.0832 mol) and the mixture was stirred for 15 h at 75° C. The reaction mixture was cooled to ambient temperature and diluted with ice water (500 mL) and the solid precipitated was filtered, washed with water and dried under vacuum affording 9.3 g (91%) of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester as a solid. MS-ESI m/z 246 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 3.8 (t, 2H), 3.9 (s, 3H), 4.5 (t, 2H), 7.8 (d, 1H), 7.9 (dd, 1H), 8.25 (s, 1H), 8.4 (s, 1H).

Provenance & Evidence