Ammonia → HCID 13674880, Verbindung

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.

1. customfor 3 hours
2. temperatureThe mixture is cooled
3. extractionThe alkaline mixture is extracted thrice with 30 ml of chloroform
4. washwashed thrice with 30 ml of water
5. dry with materialeach, dried over magnesium sulfate
6. customthe solvent is evaporated
7. distillationThe oily residue is distilled under reduced pressure
8. customFirst the excess of 2,6-dimethyl-aniline is recovered (4.6 g, 98% of the excess
9. customb.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
10. customis purified by chromatography on 80 g of silica gel
11. additiona 1:2 mixture of benzene and ethyl acetate
12. customA pure product, melting at 58°-60° C., is obtained

ORD-Eintrag

ord-d31b6a2027a54e449fd54b8f9784b6d2

Quelldatensatz

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04922021