Hydrochloric Acid → ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

Participants

Reaction Steps

4.1 g (31.9 mmol) of ethyl azidoacetate and 2.8 g (31.9 mmol) of 2-chloroacrylonitrile are stirred in 32 ml of water at a bath temperature of 80° C. for 16 h. After cooling to RT, the solution is acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated under reduced pressure. 50 ml of ethanol and 10 drops of concentrated sulphuric acid are added to the residue, and the mixture is stirred under reflux for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure, ethyl acetate is added to the residue, the suspension is washed with semiconcentrated sodium bicarbonate solution and the organic phase is dried over sodium sulphate. The solvent is removed completely on a rotary evaporator and the solid is dried under reduced pressure. Yield: 1.5 g (25% of theory)

Provenance & Evidence