Hydrochloric Acid → (5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol

HRID 1415996Notes

Reaction equation

HRID 1415996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17]CC3C=CC(OC)=CC=3)=[N:12][C:11]=2[CH:27]([CH3:29])[CH3:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>C(O)C>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:27]([CH3:29])[CH3:28])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 221305485-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole

Product 1

HCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(6)In 45 ml of ethanol was dissolved 9.10 g (20.1 mmol)of 5-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (17b), followed by addition of 90 ml of 6N-hydrochloric acid, and the mixture was refluxed for 1 hour. This reaction mixture was concentrated under reduced pressure to remove ethanol and the residue forming a couple of layers was extracted twice with n-hexane to remove p-methoxybenzyl chloride. The aqueous layer was extracted with methylene chloride and the extract was neutralized with an aqueous sodium bicarbonate solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was rinsed with isopropyl ether to provide 6.3 g (yield 95%)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (12=Compound I-8). mp 157-158° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationThis reaction mixture was concentrated under reduced pressure
  3. customto remove ethanol
  4. customthe residue forming a couple of layers
  5. extractionwas extracted twice with n-hexane
  6. customto remove p-methoxybenzyl chloride
  7. extractionThe aqueous layer was extracted with methylene chloride
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure
  10. washthe residue was rinsed with isopropyl ether

Sources & evidence

ORD record
ord-3e204c1df2324d729b1f6e41b0f59f45
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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