Benzene → 2-[1-(4-chlorophenyl)ethylideneamino]oxyacetic Acid

Participants

Reaction Steps

A solution of 1.2 g of (4-chloro-α-methylbenzylidene) amino-oxyacetyl chloride in 3 ml of benzene was added whilst stirring to a solution of 0.45 g of the hydrochloride of 2-aminoethanol in 10 ml of dimethylformamide. After the reaction mixture had been allowed to stand at room temperature for 24 hours it was mixed with 25 ml of diethylether and 25 ml of a 10% solution of potassium bicarbonate. On termination of the carbondioxide evolution the mixture was separated and the ethereal layer was washed another time with 10 ml of water. The ethereal solution was extracted with 6 ml of 2 N-hydrochloric acid and then twice with altogether 15 ml of water. The latter three extracts were combined and mixed with 2 g of potassium bicarbonate. On termination of the evolution of carbon dioxide the mixture was twice extracted with diethylether. The ethereal extracts were dried with anhydrous sodiumsulphate, concentrated by evaporation and then neutralized with 2 N alcoholic hydrochloric acid. The addition of ether to the neutralized solution resulted in the crystallisation of the hydrochloride of the (2-aminoethyl)ester of (4-chloro-α-methylbenzylidene) aminooxyacetic acid. Melting point 167°-169° C. with decomposition.

Provenance & Evidence