Hydrochloric Acid → 1-[(4-Chlorophenyl)methyl]-1H-imidazole-2-carboxylic acid

HRID 83659Notes

Reaction equation

HRID 83659 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[C:12]([OH:14])=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68379775ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate

Product 1

HCID 683797411-[(4-Chlorophenyl)methyl]-1H-imidazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(4-chlorobenzyl)-1H-imidazole-2-carboxylate (7.28 g, 27.5 mmol), was dissolved in EtOH (10 mL) and 10% aq. NaOH (20 mL) and stirred at rt for 15 h. The solvent was then stripped off, water was added, and the solution acidified with HCl. The resulting precipitate was collected over a filter and washed with 1M HCl and dried to afford the title compound as a white powder without further characterization. (Yield: 6.506 g, 27.5 mmol, 100%)

Workup

  1. customThe resulting precipitate was collected over
  2. filtrationa filter
  3. washwashed with 1M HCl
  4. customdried

Sources & evidence

ORD record
ord-a420a9d85db14e7db51511543c07ec47
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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