o-Phenetidine → N-(2-Ethoxyphenyl)-2-methylbenzamide

HRID 1287692

Reaktionsgleichung

[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Br)=[O:5].[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16])[CH3:12].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A 19.9 g (0.1 mol) portion of o-methylbenzoyl bromide was added dropwise with cooling to a mixture of 13.7 g (0.1 mol) of o-ethoxyaniline and 8.4 g (0.1 mol) of sodium bicarbonate in 200 ml of acetone with stirring. After addition of the o-methylbenzoyl bromide, the reaction mixture was warmed to 40° C and the mixture was refluxed and stirred for another 40 hours. After filtering, the ether was distilled from the reaction mixture and the residual material was re-dissolved in ether and washed with water. The ether layer was dried over anhydrous sodium sulfate, the ether was removed and the product was distilled to obtain 24.1 g (94.5%) of a clear pink liquid having a boiling point of 148° C/0.04 mm Hg and nD20 of 1.5929.

Aufarbeitung

temperaturethe mixture was refluxed
stirringstirred for another 40 hours
filtrationAfter filtering
distillationthe ether was distilled from the reaction mixture
dissolutionthe residual material was re-dissolved in ether
washwashed with water
dry with materialThe ether layer was dried over anhydrous sodium sulfate
customthe ether was removed
distillationthe product was distilled

Quellen und Nachweise

ORD-Eintrag: ord-f753bb8743d34f2faa04ac641cf2bb14
Quelldatensatz: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US03985804

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