Hydrochloric Acid → HCID 178496783, compound

Participants

Reaction Steps

A suspension of 14.1 g (0.071 mole) of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzonitrile (prepared in example 1.1 above) in 420 ml of methanol is cooled to -40° C. and saturated with gaseous hydrochloric acid. The suspension is allowed to return to 10° C. and is saturated once again with gaseous hydrochloric acid. The reaction mixture is kept at that temperature for 20 hours. The solution is concentrated to 200 ml, 300 ml of ice-cold water and 300 ml of ethyl acetate are added to the concentrated solution and the solution is then neutralized using an aqueous sodium bicarbonate solution. The solution is filtered, and the aqueous phase is separated from the organic phase, then the aqueous phase is extracted twice with 300 ml of ethyl acetate and the organic phases are combined. The organic phase is washed with a saturated aqueous sodium chloride solution, is then dried over magnesium sulfate, filtered and evaporated under reduced pressure. 15.4 g of methyl 2-hydroxy-3-(1H-imidazol- 4-ylmethyl)-benzenecarboximidate are obtained as a beige solid product which is taken up in 210 ml of absolute ethanol.

Provenance & Evidence