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

HRID 382355Notes

Reaction equation

HRID 382355 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-056a59c1f9a940fd87e11548b35443a8
Source dataset
uspto-grants-2001_10
Patent number
US06310082B1

Reaction notes

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