Hydrochloric Acid → 2-Benzyl-5-carboxy-1-(2-chlorobenzyl) benzimidazole

HRID 321970Notes

Reaction equation

HRID 321970 reaction equation
[OH-].[Na+].[CH2:3]([C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:13]2[CH:23]=[CH:24][C:25]([C:27]([O:29]CC)=[O:28])=[CH:26][C:12]=2[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(O)C>[CH2:3]([C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:13]2[CH:23]=[CH:24][C:25]([C:27]([OH:29])=[O:28])=[CH:26][C:12]=2[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 186811502-Benzyl-1-(2-chlorobenzyl)-5-ethoxycarbonylbenzimidazole

Product 1

HCID 186810562-Benzyl-5-carboxy-1-(2-chlorobenzyl) benzimidazoleYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (8 ml) and 10% sodium hydroxide aqueous solution (3.7 g) are added to 2-benzyl-1-(2-chlorobenzyl)-5-ethoxycarbonylbenzimidazole (0.635 g) (example 16), and the solution is refluxed for 4 hours. After the reaction solution is cooled, its acidity is adjusted to pH 6 with 10% hydrochloric acid. The sediment is gathered, washed with water, dried under reduced pressure, and thus, 2-benzyl-5-carboxy-1-(2-chlorobenzyl) benzimidazole (143) (0.488 g) is obtained.

Workup

  1. temperaturethe solution is refluxed for 4 hours
  2. temperatureAfter the reaction solution is cooled
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-6e571c163d974168ab2814b52233f2f1
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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