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

HRID 1857772Notes

Reaction equation

HRID 1857772 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]([CH3:29])[C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)C1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>>[Cl:27][C:25]1[CH:26]=[C:21]([S:20][C:14]2[N:13]([CH3:29])[C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[N:16][C:15]=2[CH:17]([CH3:19])[CH3:18])[CH:22]=[C:23]([Cl:28])[CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22130857HCID 22130857, compound

Product 1

HCID 4740831H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-Yield 64.5%

Conditions

Temperature
110 °C

Procedure

To 3.1 g (6.9 mmol) of the above oil (136a) was added 13 ml of concentrated hydrochloric acid and the mixture was heated at 110° C. for 2 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 (3% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 1.6 g (yield 39%) of 3-(5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)-propan-1-ol (137a) as crystals. mp 124-125° C.

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 (3% methanol-ethyl acetate)
  8. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-43377d2252f24caab0ea7c6515afd79a
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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