Methyl iodide → 4-(4-Methoxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

HRID 2425826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425826
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[CH:12][C:11]=2[CH3:17])=[C:5]([CH3:18])[CH:4]=1.[I:19][CH3:20]>C(Cl)Cl>[I-:19].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([C:10]2[C:15]([CH3:16])=[CH:14][N+:13]([CH3:20])=[CH:12][C:11]=2[CH3:17])=[C:7]([CH3:9])[CH:8]=1

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 595503344-(4-Methoxy-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

Produkt 1

HCID 669938664-(4-Methoxy-2,6-dimethyl-phenyl)-1,3,5-trimethyl-pyridinium iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4 (0.241 g, 1.00 mmol) in dry CH2Cl2 (5 mL) was added dropwise iodomethane (0.32 mL, 0.729 g, 5.10 mmol) at room temperature under N2. The reaction mixture was then refluxed at 60° C. under N2 for 1 h. After cooling to room temperature, the mixture was concentrated in vacuo to give the corresponding methylpyridinium iodide salt as an analytically pure yellow solid (0.382 g, 99.8%). mp 220-221° C.; 1H NMR (400 MHz, CD2Cl2): δ 9.079 (s, 2H), 6.751 (s, 2H), 4.579 (s, 3H), 3.881 (s, 3H), 2.135 (s, 6H), 1.854 (s, 6H); 13C NMR (100 MHz, CD2Cl2): δ 160.512, 159.866, 143.124, 138.802, 135.527, 125.927, 114.217, 55.692, 48.686, 20.188, 17.331; Anal. Calcd. For C17H22INO: C, 53.27; H, 5.79; N, 3.65. Found: C, 53.15; H, 5.79; N, 3.57.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b68d36ce859c434f9ac3dd04f45d6e37
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968016B2

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