Ammonia → HCID 13674880, compound

Participants

Reaction Steps

1-Ethylamino-2-propanol is diacetylated according to the method of W. J. Bailey and C. N. Bird [J. Org. Chem. 23, 996 (1958)], and then the ester group of the product is hydrolyzed to free hydroxy group in a 10% ethanolic potassium hydroxide solution at room temperature. The resulting 1-(N-ethyl-acetamido)-2-propanol, bp.: 100°-110° C./53.3 Pa, is chlorinated as described in Step b) of Example 31 under boiling the mixture for 3 hours, and the resulting 1-(N-ethylacetamido)-2-chloro-propane, b.p.: 102°-110° C./53.3 Pa (6.0 g, 36.7 mmoles), is reacted with 9.3 ml (9.1 g, 75 mmoles) of 2,6-dimethyl-aniline for 3 hours at 140°-145° C. under nitrogen atmosphere with stirring. The mixture is cooled, dissolved in 40 ml of a 10% aqueous hydrochloric acid solution, and the solution is rendered alkaline (pH=9) with concentrated aqueous ammonia. The alkaline mixture is extracted thrice with 30 ml of chloroform, each. The chloroform solutions are combined, washed thrice with 30 ml of water, each, dried over magnesium sulfate, and the solvent is evaporated. The oily residue is distilled under reduced pressure. First the excess of 2,6-dimethyl-aniline is recovered (4.6 g, 98% of the excess; b.p.: 52°-62° C./53.3 Pa), and then the crude 1-(N-ethyl-acetamido)-2-(2,6-dimethylphenyl-amino)-propane distils at 120°-140° C./53.3 Pa. The resulting crude product, weighing 1.9 g (21%), is purified by chromatography on 80 g of silica gel; a 1:2 mixture of benzene and ethyl acetate is applied as eluant. A pure product, melting at 58°-60° C., is obtained.

Provenance & Evidence