Hydrochloric Acid → 6-Carboxy-1-(2-Chlorobenzyl)-2-Methylbenzimidazole

HRID 840778Notes

Reaction equation

HRID 840778 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([C:16]([O:18]CC)=[O:17])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH3:21].Cl>C(O)C>[C:16]([C:13]1[CH:14]=[CH:15][C:10]2[N:9]=[C:8]([CH3:21])[N:7]([CH2:6][C:5]3[CH:22]=[CH:23][CH:24]=[CH:25][C:4]=3[Cl:3])[C:11]=2[CH:12]=1)([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 186808391-(2-Chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

Product 1

HCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (80 li) and 10% sodium hydroxide aqueous solution (37 g) are added to 1-(2-chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole (10.0 g), 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, 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (8.30 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-2bb1808f4d1e466493856bff309d35ae
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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