Dimethylformamide → 6-[(4-Chlorophenoxy)methyl]-4-phenylmorpholin-2-one

Participants

Reaction Steps

Two grams (0.0072 moles) of 1-anilino-3-(p-chlorophenoxy)-2-propanol [prepared in part (1)], 1.2 g (0.0087 moles) of K2CO3 and 2.9 g (0.0174 moles) of ethyl bromoacetate were added to 20 ml of N,N-dimethylformamide. The resulting mixture was refluxed for 5 hr with stirring. Concentration of the reaction mixture and addition of ethyl acetate and water to the residue gave a solid. The solid was collected by filtration and washed with ethyl acetate and water and dried (0.5 g). The filtrate was acidified with 10% aqueous hydrochloric acid and the organic layer was washed with water and dried over anhydrous magnesium sulfate. After the evaporation of ethyl acetate, 20 ml of acetic acid was added to the residue and refluxed for 3 hr. The reaction mixture was concentrated under reduced pressure, and 1.3 g of the solid was obtained by crystallizing the residue from ether. Recrystallization of the combined solids (1.8 g) from benzene gave 1.3 g (57%) of crystals, m.p.142°-144°.

Provenance & Evidence