Methyl iodide → 7-Methoxy-3-methyl-2-trifluoromethylbenzimidazole

HRID 275792

Reaction equation

HRID 275792 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[NH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:18]I>O1CCCC1>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[C:9]([C:12]([F:15])([F:13])[F:14])[N:8]([CH3:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178488964HCID 178488964, compound

Product 1

HCID 183166367-Methoxy-3-methyl-2-trifluoromethylbenzimidazoleYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-2-trifluoromethylbenzimidazole (1.4 g) in tetrahydrofuran (40 ml) under nitrogen was added sodium hydride (0.32 g; 60% dispersion in oil). The mixture was stirred for 20 minutes at room temperature before methyl iodide (1.35 g) was added. Stirring was continued overnight. The reaction was quenched by the addition of water (10 ml) and the solvent removed in vacuo. Ethyl acetate (50 ml) was added and the organic layer washed with saturated sodium bicarbonate solution (20 ml), water (20 ml) and brine (20 ml). Drying over anhydrous magnesium sulfate followed by the removal of the solvent in vacuo gave the title compound (1.6 g) as an oil which solidified on standing.

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of water (10 ml)
  3. customthe solvent removed in vacuo
  4. additionEthyl acetate (50 ml) was added
  5. washthe organic layer washed with saturated sodium bicarbonate solution (20 ml), water (20 ml) and brine (20 ml)
  6. dry with materialDrying over anhydrous magnesium sulfate
  7. customfollowed by the removal of the solvent in vacuo

Sources & evidence

ORD record
ord-a444ee7d83814d28be7d6d046cd41d05
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Linked notes

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