Methyl iodide → 5-Methoxy-1-methylbenzimidazole

HRID 1777128Notes

Reaction equation

HRID 1777128 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]2[NH:9][CH:10]=[N:11][C:7]=2[CH:6]=1.[CH3:14]I>CN(C=O)C.O>[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]2[N:9]([CH3:14])[CH:10]=[N:11][C:7]=2[CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178488096HCID 178488096, compound

Product 1

HCID 42927805-Methoxy-1-methylbenzimidazoleYield 54.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (972 mg, 40.5 mmol) in DMF (20 mL) was added 5-methoxy-1H-benzo[d]imidazole (2.0 g, 13.5 mmol) at 27° C. After stirring for 5 minutes, MeI (2.3 g, 16.2 mmol) was added and the resulting mixture was stirred for 16 h. The mixture was then diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the crude product (1.2 g, 54.5%) as a grown solid. This crude was used in next step without further purification. LCMS (m/z): 163.1 (M+1).

Workup

  1. stirringthe resulting mixture was stirred for 16 h
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5d83ee51e4ce4078ab5ea1f5f97824b9
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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