Hydrochloric Acid → HCID 18930641, compound

Participants

Reaction Steps

To a solution of allyl 3-(methoxycarbonylmethylureido)benzoate (5.27 g, 18.7 mmol) in THF (27 ml) is added 2N hydrochloric acid (37.4 ml), and the mixture is refluxed with stirring for 2.5 hours. After allowing to cool, water and an aqueous saturated sodium bicarbonate solution are added to the reaction solution to adjust the pH of the aqueous layer to 8, which is then extracted with ethyl acetate. Concentrated hydrochloric acid is added to the aqueous layer to adjust the pH to 1, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue is crystallized from toluene to obtain the objective compound (3.66 g). Yield 70%.

Provenance & Evidence