5,6-Dimethylbenzimidazole → HCID 929363, compound

HRID 226017Notes

Reaction equation

HRID 226017 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:15]>CN(C)C=O>[CH3:15][N:6]1[C:5]2[CH:9]=[C:10]([CH3:11])[C:2]([CH3:1])=[CH:3][C:4]=2[N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 6755,6-DimethylbenzimidazoleHCID 6328Methyl iodideHCID 24758Sodium hydride

Product 1

HCID 929363HCID 929363, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 5.00 g (34.20 mmol) of 5,6-dimethylbenzimidazole in 20 mL of dry dimethylformamide is reacted with 1.51 g (37.62 mmol) of sodium hydride at room temperature for 4 h. 2.34 mL (37.62 mmol) of iodomethane is added and reaction is allowed to stir at room temperature overnight. Reaction is quenched with water, layers are separated, extract aqueous 3×50 mL ethyl acetate, dry (MgSO4), and concentrate. The crude mixture is purified by chromatography using dichloromethane: methanol as a solvent system. Product containing fractions are combined to obtain 3.75 g of the title compound, 68% yield. MS, ES+=161.1. H1NMR (CDCl3) δ 7.98 (s, 1H); 7.37 (s, 1H); 7.29 (s, 1H); 3.74 (s, 3H); 2.31 (s, 3H); 2.28 (s, 3H) ppm

Workup

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

Sources & evidence

ORD record
ord-57ba3eb400254b45a5f62f55e93f381d
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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