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

HRID 1400665Notes

Reaction equation

HRID 1400665 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 ˜5 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-d23a1d84fe3c42c5aabd795af4b5367b
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

Loading…