Hydrochloric Acid → HCID 54561726, compound

HRID 276041Notes

Reaction equation

HRID 276041 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]([O:18]C)=[O:17])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:20].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54285950HCID 54285950, compound

Product 1

HCID 54561726HCID 54561726, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above-mentioned crude methyl 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acrylate (3.29 g) was dissolved in 20 ml of ethanol, and 10.1 g of a 5% sodium hydroxide aqueous solution were added thereto. The mixture was refluxed for 2 hours. The reaction solution was neutralized with a hydrochloric acid aqueous solution. The solvent was distilled off under reduced pressure, and the residue was purified through silica-gel chromatography (eluent: a mixture of chloroform and methanol at a ratio of from 9:1 to 6:1) to give 1.10 g of 1-(2-chlorobenzyl)-2-methylbenzimidazole-6-acrylic acid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified through silica-gel chromatography (eluent
  4. additiona mixture of chloroform and methanol at a ratio of from 9:1 to 6:1)

Sources & evidence

ORD record
ord-5c0aa9003f3b48908f89214d7f789399
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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