Hydrochloric Acid → 1H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-(2-hydroxyethyl)-4-(1-methylethyl)-

HRID 1416069Notes

Reaction equation

HRID 1416069 reaction equation
Cl.C([O:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]([CH2:30][CH2:31][OH:32])[C:15]([S:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[C:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:29][C:24]1[CH:23]=[C:22]([S:21][C:15]2[N:14]([CH2:30][CH2:31][OH:32])[C:13]([CH2:12][CH2:11][CH2:10][OH:9])=[N:17][C:16]=2[CH:18]([CH3:20])[CH3:19])[CH:27]=[C:26]([Cl:28])[CH:25]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4741011H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(3-(phenylmethoxy)propyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 4741021H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-(2-hydroxyethyl)-4-(1-methylethyl)-Yield 26.6%

Conditions

Temperature
110 °C

Procedure

To 14 ml of concentrated hydrochloric acid, 1.4 g (2.9 mmol)of the alcohol (136e)was added and the mixture was heated at 110° C. for 7 hours. After cooling, the mixture was neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol-ethyl acetate)to provide 300 mg (yield 26%)of 3-(5-(3,5-dichlorophenylthio)-1-(2-hydroxyethyl)-4-isopropyl-1H-imidazol-2-yl)-propan-1-ol (137d)as oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-afd275d128814ae8aa4e5aa1c5bfc309
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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