Hydrochloric Acid → HCID 18680830, compound

HRID 321969Notes

Reaction equation

HRID 321969 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) (example 10), 5% sodium hydroxide aqueous solution (2.8 g) is added, and the solution is refluxed for 1.5 hours. The solution is made acidic using 1N hydrochloric acid, and is 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 (0.30 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 for 1.5 hours
  2. concentrationis concentrated under reduced pressure
  3. additionEthanol is added to the residue and organic materials
  4. extractionare extracted
  5. customThe ethanol is removed under reduced pressure

Sources & evidence

ORD record
ord-ae0395a30a80438ab5969ae78735bb67
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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