Hydrochloric Acid → HCID 18680830, compound

HRID 1699615Notes

Reaction equation

HRID 1699615 reaction equation
[CH2:1]([C:8]1[N:12]([CH3:13])[C:11]2[CH:14]=[C:15]([C:18]([O:20]CC)=[O:19])[CH:16]=[CH:17][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[ClH:25]>C(O)C>[ClH:25].[CH2:1]([C:8]1[N:12]([CH3:13])[C:11]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9926144HCID 9926144, compound

Product 1

HCID 18680830HCID 18680830, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (4 ml) solution of 2-benzyl-6-ethoxycarbonyl-1-methylbenzimidazole (0.340 g), 5% sodium hydroxide aqueous solution (2.8 g) is added, and the solution is refluxed by heating for 1.5 hours. The solution is made acidic using 1N hydrochloric acid and concentrated under reduced pressure. Ethanol is added to the residue and organic materials are extracted. The ethanol is removed under reduced pressure and thus, 2-benzyl-6-carboxy-1-methylbenzimidazole hydrochloride (0.300 g) is obtained. 1H-NMR (DMSO-d6, δ): 4.00 (3H, s), 4.62 (2H, s), 7.33 (1H, m), 7.35-7.45 (4H, m), 7.83 (1H, d, J=8.4 Hz), 8.06 (1H, d, J=8.4 Hz), 8.42 (1H, s), 13.3 (1H, br s).

Workup

  1. temperaturethe solution is refluxed
  2. temperatureby heating for 1.5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionEthanol is added to the residue and organic materials
  5. extractionare extracted
  6. customThe ethanol is removed under reduced pressure

Sources & evidence

ORD record
ord-9ee1bccf78114398b42d75fece0ce9a3
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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