Potassium Carbonate → N-(2',6'-dichloro-4'-methylphenyl)-4-methylaniline

HRID 603349

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[C:3]=1O.C(=O)([O-])[O-].[K+].[K+].ClCC([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=O.ClC1C=C(C)C=C(Cl)C=1OCC(NC1C=CC(C)=CC=1)=O.C[O-].[Na+]>CC(O)C.CO.CCCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

12 g (67 mmol) of 2,6-dichloro-4-methylphenol are dissolved in 25 ml of 2-propanol followed by the addition of 10.5 g (76 mmol) of potassium carbonate and 12.8 g (70 mmol) of 2-chloro-N-(4-methylphenyl)acetamide. The mixture is refluxed for 4 h. At this time, the formation of A: 2-(2′,6′-dichloro-4′-methylphenoxy)-N-(4-methylphenyl)acetamide is completed. 13.6 ml of sodium methylate solution 30% in methanol are slowly added and the temperature is increased to about 85° C. by distilling 25 ml of solvent. The mixture is stirred 2 h more to complete the formation of B. 25 ml of water are added at 70° C. to obtain a 2 phases solution. The lower layer is discarded. The upper layer is diluted with 20 ml of heptane-fraction and washed with 2×20 ml of water. The organic phase is separated and concentrated in vacuo to obtain N-(2′,6′-dichloro-4′-methylphenyl)-4-methylaniline as a crude oil. GC/MS: 265 (100, M+), 195 (130).

Aufarbeitung

temperatureThe mixture is refluxed for 4 h
distillationby distilling 25 ml of solvent
addition25 ml of water are added at 70° C.
customto obtain a 2 phases solution
washwashed with 2×20 ml of water
customThe organic phase is separated
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-0161b63b7b774b7187cb7b9c172fc709
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07906677B2

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