Sodium Iodide → 4-(2,6-Dimethylbenzylamino)-2-methylbenzimidazole

HRID 991589Notes

Reaction equation

HRID 991589 reaction equation
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C.C(Cl)Cl.CO>[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 178432166HCID 178432166, compound

Product 1

HCID 1784321684-(2,6-Dimethylbenzylamino)-2-methylbenzimidazoleYield 30.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4-amino-2-methylbenzimidazole (6.0 g, 0.041 mol) was dissolved in acetonitrile (120 ml). To the solution were added 2,6-dimethylbenzylchloride (6.3 g, 0.041 mol), sodium carbonate (16 g, 0.15 mol) and a cat. amount of sodium iodide and the reaction mixture was refluxed for 3 h. The sodium carbonate was removed by filtration and was washed with methylene chloride. Vacuum evaporation of the solvent gave an oily residue which was subjected to flash chromatography on silica gel, methylene chloride: methanol (10:1). The residue was crystallized by treating with ethyl acetate to obtain 3.3 g ( 30%) of the title compound.

Workup

  1. customThe sodium carbonate was removed by filtration
  2. washwas washed with methylene chloride
  3. customVacuum evaporation of the solvent
  4. customgave an oily residue which
  5. customThe residue was crystallized
  6. additionby treating with ethyl acetate

Sources & evidence

ORD record
ord-3cfdfb5136d847588528cfbdbb9bc715
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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