Sodium Hydroxide → 3-Benzyl-1,3-benzodiazole-5-carboxylic acid

HRID 1258937Notes

Reaction equation

HRID 1258937 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([C:17]([O:19]CC)=[O:18])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58213808ethyl 3-benzyl-3H-benzo[d]imidazole-5-carboxylate

Product 1

HCID 582138253-Benzyl-1,3-benzodiazole-5-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 3-benzyl-3H-benzo[d]imidazole-5-carboxylate (0.12 g, 0.43 mmol) in ethanol (10 mL) was added NaOH (0.12 g in 2 mL of H2O) and then the solution was stirred for 24 hr at room temperature. The reaction solution was then concentrated, diluted with water (10 mL) and then the pH was adjusted to using 1N HCl. The aqueous layer was then saturated with NaCl and extracted with ethyl acetate (2×50 mL). Then organic layer was dried (MgSO4), filtered and then concentrated to provide 0.1 g (93%) of 3-benzyl-3H-benzo[d]imidazole-5-carboxylic acid as an off-white solid.

Workup

  1. concentrationThe reaction solution was then concentrated
  2. additiondiluted with water (10 mL)
  3. extractionsaturated with NaCl and extracted with ethyl acetate (2×50 mL)
  4. dry with materialThen organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1ab8fcc735c40009d3cb635833ed114
Source dataset
uspto-grants-2013_06
Patent number
US08466193B2

Reaction notes

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