Hydrochloric Acid → HCID 18681093, compound

HRID 1699608Notes

Reaction equation

HRID 1699608 reaction equation
[OH-].[Na+].C(O)C.[CH2:6]([N:13]1[C:17]2[CH:18]=[C:19]([C:22]([O:24]CC)=[O:23])[CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:27][CH2:28][CH3:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>O>[CH2:6]([N:13]1[C:17]2[CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[CH2:27][CH2:28][CH3:29])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 18681060HCID 18681060, compound

Product 1

HCID 18681093HCID 18681093, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10% sodium hydroxide aqueous solution (3.61 g), ethanol (5 ml), and water (3 ml) are added to 1-benzyl-6-ethoxycarbonyl-2-n-propylbenzimidazole (0.97 g) (example 51), and the solution is refluxed by heating for one hour. The acidity of the reaction solution is adjusted to pH 6 with 10% hydrochloric acid. The solution is concentrated under reduced pressure, ethanol is added to the obtained residue, and the inorganic salt is separated through filtration. The filtrate is concentrated under reduced pressure, and 1-benzyl-6-carboxy-2-n-propylbenzimidazole (0.85 g) (example 80) is obtained. 1H-NMR (DMSO-d6, δ): 0.94 (3H, t, J=7.4 Hz), 1.73-1.81 (2H, m), 2.85 (2H, t, J=7.3 Hz), 5.59 (2H, s), 7.07 (2H, dd, J=1.1 and 8.3 Hz), 7.27 (1H, t, J=7.3 Hz), 7.33 (2H, t, J=7.4 Hz), 7.65 (1H, d, J=8.4 Hz), 7.79 (1H, dd, J=1.5 and 8.4 Hz), 8.04 (1H, s).

Workup

  1. temperaturethe solution is refluxed
  2. temperatureby heating for one hour
  3. concentrationThe solution is concentrated under reduced pressure, ethanol
  4. additionis added to the obtained residue
  5. customthe inorganic salt is separated through filtration
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d5f33725e7f142c1ba149e8c8534c551
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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