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

HRID 1857774Notes

Reaction equation

HRID 1857774 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]([CH2:29][CH3:30])[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]([CH2:29][CH3:30])[C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[N:16][C:15]=2[CH:17]([CH3:18])[CH3:19])[CH:22]=[C:23]([Cl:28])[CH:24]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22130218HCID 22130218, compound

Product 1

HCID 4740851H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-Yield 75.2%

Conditions

Temperature
110 °C

Procedure

To 5.3 g (11.4 mmol) of the above oil (136b) was added 24 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, arid concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol-ethyl acetate) and recrystallized from n-hexane to provide 3.2 g (yield 75%) of 3-(5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)-propan-1-ol (137b) as crystals. mp 73° 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. concentrationarid concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (3% methanol-ethyl acetate)
  7. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-fd10960f67d64e5286a29126e8111071
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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