Benzyl Bromide → Methyl 1-benzyl-1H-benzimidazole-5-carboxylate

HRID 1419123Notes

Reaction equation

HRID 1419123 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2779733methyl 1H-1,3-benzodiazole-5-carboxylate

Product 1

HCID 54450488Methyl 1-benzyl-1H-benzimidazole-5-carboxylateYield 22.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.8 g of methyl 5-benzimidazolecarboxylate (prepared as described in Preparation 26), 3.52 g of benzyl bromide, 3 g of potassium carbonate and 50 ml of acetone was stirred for 3 days at room temperature. At the end of this time, the solvent was removed by evaporation under reduced pressure and the residue was mixed with an aqueous solution of sodium chloride, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was then recrystallized from a mixture of ethyl acetate and hexane, to give 0.94 g of the title compound, melting at 156°-162° C.

Workup

  1. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  2. additionthe residue was mixed with an aqueous solution of sodium chloride
  3. extractionafter which it was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. customThe residue was then recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ba3e220a895f48f4abeccf9969b9d70b
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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