1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)-1,3-thiazole

Participants

Reaction Steps

Diphenylphosphoryl azide (3.25 mL, 0.015 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.25 mL, 0.025 mol) were added to a solution of thiazol-2-yl-methanol (1.44 g, 0.013 mol) in toluene (20 mL) at 0° C. After 1 h the reaction was warmed to room temperature and stirred overnight. The mixture was diluted with toluene (20 mL) and washed with H2O (3×) brine (1×), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (30% ethyl acetate/hexanes) to afford the azide as a tan oil (1.1 g, 63%). IR 2098 cm. 1H NMR (250 MHz, CDCl3) δ 7.8 (d, 1H, J=2.0 Hz); 7.4 (d, 1H, J=2.0 Hz); 4.7 (s, 2H).

Provenance & Evidence