Potassium Hydroxide → 2-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propylthio]benzimidazole

HRID 2118791Notes

Reaction equation

HRID 2118791 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].[C:13]([C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH2:22][CH2:23]Br)=[C:18]([CH2:27][CH2:28][CH3:29])[C:17]=1[OH:30])(=[O:15])[CH3:14]>C(O)C.ClCCl.O>[C:13]([C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH2:22][CH2:23][S:1][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[C:18]([CH2:27][CH2:28][CH3:29])[C:17]=1[OH:30])(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 178527775HCID 178527775, compound

Product 1

HCID 137714632-[3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propylthio]benzimidazoleYield 81.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a suspension of 1.2 g of 2-mercaptobenzimidazole in 30 ml of ethanol was added 580 mg of potassium hydroxide under stirring and stirred at room termperature for 10 minutes. To this solution was added 2.8 g of 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylbromide at one time, and stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and resulting residue was diluted with dichloromethane-water, then extracted with dichloromethane three times. The organic layer was combined, then washed with water saturated with sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the resulting residue was recrystallized from dichloromethane-n-hexane to give 2.5 g (yield 81%) of the aimed compound as colorless powder. mp 149°-150° C.

Workup

  1. stirringstirred at room termperature for 10 minutes
  2. stirringstirred at room temperature for 4 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. customresulting residue
  5. extractionextracted with dichloromethane three times
  6. washwashed with water saturated with sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resulting residue was recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-9f018023b8264c6d8d4c2228b2e7daaa
Source dataset
uspto-grants-1987_07
Patent number
US04680398

Reaction notes

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