Sodium Bicarbonate → {4-[(3-Chlorophenyl)sulfanyl]-1-methyl-5-(propan-2-yl)-1H-imidazol-2-yl}methanol

HRID 1857714Notes

Reaction equation

HRID 1857714 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH3:26])[C:12]([CH:23]([CH3:25])[CH3:24])=[C:13]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[N:14]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>Cl>[Cl:22][C:18]1[CH:17]=[C:16]([S:15][C:13]2[N:14]=[C:10]([CH2:9][OH:8])[N:11]([CH3:26])[C:12]=2[CH:23]([CH3:25])[CH3:24])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22130223HCID 22130223, compound

Product 1

HCID 473947{4-[(3-Chlorophenyl)sulfanyl]-1-methyl-5-(propan-2-yl)-1H-imidazol-2-yl}methanolYield 65%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

In 5.8 ml of concented hydrochloric acid was dissolved 580 mg (1.5 mmol) of 2-benzyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole (17ab'), and the mixture was refluxed under heating at 110° C. for 6 hours. The reaction mixture was neutlized with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product was recrystallized from ethyl acetate-isopropyl ether to give 289 mg of the objective Compound I-38 (yield 65%). mp 105-106° C.

Workup

  1. temperaturewas refluxed
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude product was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-05f229b14abf4978ab008b7f87a3e0d1
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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