Hydrochloric Acid → 2-Benzimidazolecarboxylic acid

HRID 1850250Notes

Reaction equation

HRID 1850250 reaction equation
C[O:2][C:3]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)=[O:4].Cl>[OH-].[Na+].CO>[NH:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=[C:5]1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 576526methyl 1H-1,3-benzodiazole-2-carboxylate

Product 1

HCID 2332402-Benzimidazolecarboxylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1H-benzoimidazole-2-carboxylic acid methyl ester (18) (0.89 g, 5.1 mmol) in 2 N aq. NaOH (10 mL) and MeOH (10 mL) was stirred at RT for 18 h. The mixture was acidified to pH=4 with 1 N aqueous HCl. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and evaporated to obtain compound (19) as a brown solid (0.67 g, yield 80%). ESI-MS (M+1): 163 calc. for C8H6N2O2 162.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-6e8549f2c8f74af2b7ad9b2ae567afdd
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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