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Water → methyl 4-[(1H-benzoimidazol-1-yl)methyl]benzoate

HRID 1988790
Notes
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Reaction equation

HRID 1988790 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N:13]1([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 2823606methyl 4-[(1H-benzoimidazol-1-yl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
23 °C

Procedure

Referring to Scheme 1, a solution of methyl 4-bromomethylbenzoate (0.5 mmol) in DMF (2.5 mL) was treated with benzimidazole (0.5 mmol) and solid K2CO3 (0.6 mmol). After stirring at 23° C. for 4 h, the reaction was poured into water (10 mL) and the resulting solid was isolated by filtration. The filter cake was rinsed with water and allowed to dry in vacuo to yield methyl 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoate.

Workup

  1. customthe resulting solid was isolated by filtration
  2. washThe filter cake was rinsed with water
  3. customto dry in vacuo

Sources & evidence

ORD record
ord-69e36956b216400eb2b77bfcd760174a
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07642275B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes