Dichloromethane → HCID 178432169, compound

HRID 991591Notes

Reaction equation

HRID 991591 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:27]=[C:26]([F:28])[CH:25]=[C:24]([CH3:29])[C:14]=1[CH2:15]C(Br)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>C(#N)C.O>[CH3:12][C:13]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([CH3:29])[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 6344DichloromethaneHCID 11430Potassium CarbonateHCID 543193582,6-Dimethyl-4-fluoro-benzylbenzylbromideHCID 178432166HCID 178432166, compound

Product 1

HCID 178432169HCID 178432169, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

4-amino-2-methylbenzimidazole (0.6 g, 4,1 mmol) was dissolved in acetonitrile (10 ml). To the solution were added 2,6-dimethyl-4-fluoro-benzylbenzylbromide (0.89 g, 4,1 mol) and potassium carbonate (0.68 g, 4.9 mmol) and the mixture was warmed at 70-80° C. for 3 h. The reaction mixture was cooled to room temperature and methylene chloride (25 ml) and water (25 ml) was added. The organic layer was separated, dried over sodium sulfate and was evaporated under reduced pressure. The residue was crystallized twice from ethyl acetate and was purified by column chromatography on silica gel, using methylene chloride containing 10% methanol as eluent. There was obtained 0.26 g (22%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customwas evaporated under reduced pressure
  5. customThe residue was crystallized twice from ethyl acetate
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3aeb52728d2142839e0b91a3772c470f
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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