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

HRID 1857755Notes

Reaction equation

HRID 1857755 reaction equation
Cl.C([O:9][CH2:10][C:11]1[N:12]([CH2:28][CH2:29][OH:30])[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>>[Cl:27][C:22]1[CH:21]=[C:20]([S:19][C:13]2[N:12]([CH2:28][CH2:29][OH:30])[C:11]([CH2:10][OH:9])=[N:15][C:14]=2[CH:16]([CH3:18])[CH3:17])[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4740901H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-((phenylmethoxy)methyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 4740911H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-4-(1-methylethyl)-Yield 67%

Conditions

Temperature
110 °C

Procedure

Added was 18 ml of cocentrated hydrochloric acid to 1.8 g (4.0 mmol) of the alcohol compound (118c), and the mixture was stirred with heating 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 anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 960 mg of 2-(5-(3,5-dichlorophenyl-thio)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)ethanol (119b) as oil (yield 67%).

Workup

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

Sources & evidence

ORD record
ord-f56d041f5b474689aac9aed1bf232bbf
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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