Methyl iodide → 5-Methoxy-1-methylbenzimidazole

HRID 226019Notes

Reaction equation

HRID 226019 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.[H-].[Na+].I[CH3:15]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]([CH3:15])[CH:8]=[N:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 785985-methoxy-1H-benzimidazole

Product 1

HCID 42927805-Methoxy-1-methylbenzimidazoleYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 5.00 g (37.75 mmol) of 5-methoxybenzimidazole in 20 mL of dry dimethylformamide is reacted with 1.66 g (41.53 mmol) of sodium hydride at room temperature for 4 h. 2.58 mL (41.53 mmol) of iodomethane is added and reaction is allowed to stir at room temperature overnight. Reaction is quenched with water, layers are separated, extracted aqueous 3×50 mL ethyl acetate, dried (MgSO4), and concentrated. The crude mixture is purified by chromatography using dichloromethane: methanol as a solvent system. Product containing fractions are combined to obtain 3.50 g of the title compound which is used as is, 57% yield.

Workup

  1. customreaction
  2. customReaction
  3. customis quenched with water, layers
  4. customare separated
  5. extractionextracted aqueous 3×50 mL ethyl acetate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude mixture is purified by chromatography
  9. additionProduct containing fractions

Sources & evidence

ORD record
ord-eea1eb9a50e44820b6fb4f2f606175bc
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

Loading…