Hydrochloric Acid → 2-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylic acid

HRID 2165934Notes

Reaction equation

HRID 2165934 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][S:11][C:12]2[NH:13][C:14]3[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].Cl>[OH-].[Na+]>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][S:11][C:12]2[NH:13][C:14]3[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23042703Ethyl 2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylate

Product 1

HCID 146280452-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylic acidYield 77.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The above ester (2.20 g) was added to 1 N sodium hydroxide solution (20 ml), and the mixture was refluxed for 30 minutes, then poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-methanol (10:1), and recrystallized from n-hexane-ethyl acetate to give the title compound (1.60 g, 77.1 %) as colorless crystals, mp 108-110° C.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane-methanol (10:1)
  8. customrecrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-8552206e7a194e3795da9b6bec75b37e
Source dataset
uspto-grants-1990_07
Patent number
US04942245

Reaction notes

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