Methyl iodide → 4-(2,6-Dimethyl-4-fluorobenzylamino)-2,2-dimethylbenzimidazole

HRID 991596Notes

Reaction equation

HRID 991596 reaction equation
[CH3:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([CH3:21])[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.[OH-].[Na+].[CH3:24]I>COCCOC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:14]2[C:10](=[N:11][C:12]([CH3:24])([CH3:15])[N:13]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178432169HCID 178432169, compound

Product 1

HCID 867585704-(2,6-Dimethyl-4-fluorobenzylamino)-2,2-dimethylbenzimidazoleYield 76.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-(2,6-Dimethyl-4-fluorobenzylamino)-2-methylbenzimidazole (0.1 g, 0.35 mmol) was dissolved in 1,2-dimethoxyethane (3 ml). Solid sodium hydroxide (25 mg, 0.63 mmol) and tetrabutylammonium bromide (5 mg, 0.016 mmol) were added. The mixture was stirred 15 minutes at ambient temperature. Methyl iodide (60 mg 0.42 mmol) was added and the reaction mixture was stirred at ambient temperature for 2.5 h. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using methylene chloride: ethyl acetate (50: 50) as eluent. 80 mg (76%) of the title compound was obtained.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 2.5 h
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-31147a9adb5e4e65967c3cea1f444ef4
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

Loading…