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

HRID 1276900Notes

Reaction equation

HRID 1276900 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:19].[OH-].[Na+].Cl>C(O)C>[C:14]([C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([CH3:19])[N:5]([CH2:4][C:3]3[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=3[Cl:1])[C:9]=2[CH:10]=1)([OH:16])=[O:15]

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 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 60.0 g of 1-(2-chlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole were added 240 g of a 10% sodium hydroxide aqueous solution and 200 ml of ethanol, and the mixture was heat-refluxed for 2 hours. The reaction solution was cooled, and was then adjusted to a pH of 6 with 10% hydrochloric acid. The crystals precipitated were separated through filtration, and were dried to give 54.7 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (121).

Workup

  1. temperaturethe mixture was heat-refluxed for 2 hours
  2. temperatureThe reaction solution was cooled
  3. customThe crystals precipitated
  4. customwere separated through filtration
  5. customwere dried

Sources & evidence

ORD record
ord-fd357f85883b41a982632eb13edd1596
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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