Methyl iodide → Methyl 1-methyl-1H-benzimidazole-2-carboxylate

HRID 1850286Notes

Reaction equation

HRID 1850286 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)=[O:4].[H-].[Na+].I[CH3:17]>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576526methyl 1H-1,3-benzodiazole-2-carboxylate

Product 1

HCID 2802598Methyl 1-methyl-1H-benzimidazole-2-carboxylateYield 94.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1H-benzoimidazole-2-carboxylic acid methyl ester (18) (177 mg, 1.0 mmol) in dry DMF (5 mL) was added sodium hydride (applied as 60% dispersion in oil, 62 mg, 1.5 mmol)) at 0° C. under N2 atmosphere. After 0.5 h, iodomethane (284 mg, 2.0 mmol) was added slowly. The reaction mixture was stirred at RT for 4 h. The reaction was diluted with brine at 0° C. and extracted with EtOAc (3×20 mL). The combined organics were washed with water (2×15 mL), brine (20 mL), dried over sodium sulfate and filtered. The filtrate was concentrated and purified by flash column chromatography to provide the title compound (81) (180 mg, 90% yield) as a light yellow solid.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organics were washed with water (2×15 mL), brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-a02f0e1aa4e3487a86fe7e7839464264
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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