2,4,6-Trimethylaniline → 1-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

HRID 49750

Reaktionsgleichung

Reaktionsgleichung von HRID 49750
[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].[CH3:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:13][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[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[N:5]=1)[CH3:11]

Komponenten

5

Edukt 2

HCID 69132,4,6-TrimethylanilineHCID 707902,6-Diacetylpyridine

Produkt 1

HCID 221344681-{6-[(1E)-N-(2,4,6-Trimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-oneAusbeute 28,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2,6-Diacetylpyridine (7.3 g, 44.8 mmol) (ex. Aldrich) and 2,4,6-trimethylaniline (5.74 g, 42.55 mmol) (ex. Aldrich) were dissolved in 450 ml of toluene. To this solution, 4 Å molecular sieves and a small amount of p-toluenesulphonic acid (0.22 mmol) (ex. Aldrich) were added. The mixture was refluxed for 16h. After filtration the solvent was removed in vacuo. Several crystallisations from ethanol yielded 3.42 g (28.7%) of monoimine (1). 1H-NMR (CDCl3) δ 8.55 (d, 1H, Py-Hm), 8.11 (d, 1H, Py-Hm), 7.92 (t, 1H, Py-Hp), 6.89 (s, 2H, ArH), 2.77 (s, 3H, Me), 2.27 (s, 3H, Me), 2.22 (s, 3H, Me), 1.99 (s, 6H, Me).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 16h
  2. filtrationAfter filtration the solvent
  3. customwas removed in vacuo
  4. customSeveral crystallisations from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-27b39c33130e4d7f994f10cac286d30b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710006B2

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