Methyl iodide → 4-(2,6-Dimethylbenzylamino)-1,2-dimethylbenzimidazole

HRID 991593Notes

Reaction equation

HRID 991593 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][NH:5][C:6]1[C:14]2[NH:13][C:12]([CH3:15])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.CI.[C:23](=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>C(#N)C>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][NH:5][C:6]1[C:14]2[N:13]=[C:12]([CH3:15])[N:11]([CH3:23])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 1784321684-(2,6-Dimethylbenzylamino)-2-methylbenzimidazole

Product 1

HCID 184146854-(2,6-Dimethylbenzylamino)-1,2-dimethylbenzimidazoleYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2,6-dimethylbenzylamino)-2-methylbenzimidazole (0.2 g 0.75 mmol) was dissolved in acetonitrile (15 ml). To the solution were added methyl iodide (0.05 ml 0.82 mmol) and potassium carbonate (0.2 g 1.4 mmol) and the reaction mixture was stirred at ambient temperature for 20 h. The solids were 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). Crystallization from acetonitrile gave 0.018 g (9%) of the title compound.

Workup

  1. customThe solids were removed by filtration
  2. washwas washed with methylene chloride
  3. customVacuum evaporation of the solvent
  4. customgave an oily residue which
  5. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-7d573782c0e34a369955631258043760
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

Loading…