Hydrochloric Acid → 1-(2,4-Dichlorobenzyl)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

HRID 1276893Notes

Reaction equation

HRID 1276893 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:25]=[C:24]([Cl:26])[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][C:24]([Cl:26])=[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 225087251-(2,4-Dichlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole

Product 1

HCID 225088211-(2,4-Dichlorobenzyl)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acidYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10% sodium hydroxide aqueous solution (3.10 g) and 10 ml of ethanol were added to 0.94 g of 1-(2,4-dichlorobenzyl)-6-ethoxycarbonyl-2-methylbenzimidazole, and the mixture was heat-refluxed for 1 hour. The reaction solution was adjusted to a pH of 6 with 10% hydrochloric acid. The crystals precipitated were separated through filtration, and were dried to give 0.68 g of 6-carboxy-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole (129).

Workup

  1. temperaturethe mixture was heat-refluxed for 1 hour
  2. customThe crystals precipitated
  3. customwere separated through filtration
  4. customwere dried

Sources & evidence

ORD record
ord-e9a290eaa5174d29a6209eb32d724901
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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