Water → 1-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

HRID 889546

Reaktionsgleichung

Reaktionsgleichung von HRID 889546
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16].O>CCCCCCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[N:16]=[C:10]([C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=1)[CH3:11]

Komponenten

6

Edukt 3

HCID 962WaterHCID 707902,6-DiacetylpyridineHCID 1130332-Chloro-4,6-dimethylaniline

Produkt 1

HCID 594646241-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanoneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

20 g of 2,6-diacetylpyridine (0.123 mol), 19.08 g of 2-chloro-4,6-dimethylaniline (0.123 mol) and 0.5 g of p-toluenesulfonic acid were heated under reflux on a water separator in 500 ml of heptane for 75 min. The insoluble solid was filtered off. The solvent was distilled off from the filtrate down to 150 ml, and the remaining filtrate was cooled to room temperature, while stirring. 25.3 g of a yellow solid precipitated out. This was filtered off and recrystallized from 60 ml of hot isopropanol. A total of 12.9 g (0.043 mol) of 1-{6-[1-(2-chloro-4,6-dimethylphenylimino)ethyl]-pyridin-2-yl}ethanone were obtained in a yield of 35%.

Aufarbeitung

  1. filtrationThe insoluble solid was filtered off
  2. distillationThe solvent was distilled off from the filtrate down to 150 ml
  3. custom25.3 g of a yellow solid precipitated out
  4. filtrationThis was filtered off
  5. customrecrystallized from 60 ml of hot isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-7332f793a6874445b5f40ea32fa9a0de
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252875B2

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