Sodium Hydroxide → HCID 178432176, compound

HRID 991590Notes

Reaction equation

HRID 991590 reaction equation
[OH: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.[OH-].[Na+]>C(#N)C>[CH3:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:14]=1[CH2:15][O: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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2211542,6-Dimethylbenzyl ChlorideHCID 178432174HCID 178432174, compound

Product 1

HCID 178432176HCID 178432176, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-hydroxy-2-methylbenzimidazole (0.59 g, 4 mmol) was dissolved in acetonitrile (15 ml). To the solution were added 2,6-dimethylbenzylchloride (0.52 g, 4 mmol) and sodium hydroxide (0.16 g, 4 mmol) (dissolved in 1 ml water) and the reaction mixture was refluxed for 2 h. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride and was washed with 2 M NaOH. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The oily residue was purified by column chromatography on silica gel. The product was eluted with methylene chloride containing 5% methanol. Crystallization from acetonitrile gave 0.18 g (18%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwas washed with 2 M NaOH
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe oily residue was purified by column chromatography on silica gel
  9. washThe product was eluted with methylene chloride containing 5% methanol
  10. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-c35c2aaf6f664a3daf6d5038386c808b
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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