Methyl iodide → 2-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

HRID 382355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382355
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[OH-].[K+].[CH3:23]I>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:23])[C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([NH2:20])=[O:19])[C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178488846HCID 178488846, Verbindung

Produkt 1

HCID 105407722-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-(4′-Methoxyphenyl)benzimidazole-4-carboxamide (NU1076 from Example 5) (105.3 mg, 0.394 mmol) and powdered potassium hydroxide (22 mg, 0.394 mmol) were suspended in acetone (4 ml) and stirred until all the solids had dissolved. Methyl iodide (24.6 μll, 0.394 mmol) was added and the reaction stirred at room temperature overnight. The solvent was removed under reduced pressure and the white solid residue purified by column chromatography with dichloromethane/methanol 95:5 to give fine white crystals of the title compound. (33.2 mg, 30%) mp 289-292° C.; Found C 68.62 H 5.36 N 14.67 C16Hl5N3O2 Requires C 68.33 H 5.34 N 14.95; vmax(cm−1) 3309.23, 3141.44, 1671.29, 1605.30, 1255.08, δH 3.95 (3H, s), 4.02 (3H, s), 7.22-7.27 (2H, d), 7.44-7.52 (1H, t), 7.86-8.00 (5H, m), 9.4 (1H, br s, NH); m/z (EI) 281 (M+), 264, 250.

Aufarbeitung

  1. dissolutionhad dissolved
  2. stirringthe reaction stirred at room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe white solid residue purified by column chromatography with dichloromethane/methanol 95:5

Quellen und Nachweise

ORD-Eintrag
ord-056a59c1f9a940fd87e11548b35443a8
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310082B1

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