Acetic Acid → HCID 178432154, compound

HRID 1870935Notes

Reaction equation

HRID 1870935 reaction equation
[C:1](O)(=O)[CH3:2].[NH2:5][C:6]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>Cl>[CH3:1][C:2]1[NH:5][C:6]2[C:7]([C:8]([OH:10])=[O:9])=[CH:11][CH:12]=[CH:13][C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 1980692,3-Diaminobenzoic acid

Product 1

HCID 178432154HCID 178432154, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Acetic acid (0.23 ml) was added to a solution of 2,3-diaminobenzoic acid (200 mg, 1.32 mmol) in hydrochloric acid (4M, 3.2 ml) and the mixture was refluxed for 1 hour. Solvents were evaporated and the residual solid was redissolved in boiling methanol (5 ml) and decolorised with activated charcoal. Removal of the solvent furnished 2-methylbenzimidazole-4-carboxylic acid as an amorphous white solid (167.5 mg, 72%); δH (d6 -DMSO) 2.9 (3H, s, imidazole-2-CH3), 7.6-7.8 (1H, t, Ar-5H) 8.1 (2H, d, Ar-4/6H); m/z (EI 176 (M+), 158, 130.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customSolvents were evaporated
  3. dissolutionthe residual solid was redissolved
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-9f262bb11ae244eaa3067683d2ec15e8
Source dataset
uspto-grants-2000_08
Patent number
US06100283

Reaction notes

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