Sodium Bicarbonate → 1H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-alpha,alpha-dimethyl-4-(1-methylethyl)-

HRID 1857786Notes

Reaction equation

HRID 1857786 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>Cl>[Cl:26][C:21]1[CH:20]=[C:19]([S:18][C:12]2[N:11]([CH2:27][C:28]([OH:31])([CH3:29])[CH3:30])[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:17])[CH3:16])[CH:24]=[C:23]([Cl:25])[CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22130053HCID 22130053, compound

Product 1

HCID 4741061H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-2-(hydroxymethyl)-alpha,alpha-dimethyl-4-(1-methylethyl)-Yield 53%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

In 2 ml of concentrated hydrochloric acid was dissolved 350 mg (0.73 mmol) of the benzyl compound (140b) and the solution was stirred under heating at 110° C. for 3 hours. To this reaction mixture was added a saturated aqueous solution of NaHCO3 and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate and the extract was washed with water and dried. The solvent was then distilled off and the residue was purified by silica gel column chromatography (ethyl acetate) to provide 150 mg (yield 53%) of Compound I-153 as crystals. mp 181-182° C.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. distillationThe solvent was then distilled off
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-45b87e7d25ae4bb39871ff072d6160cd
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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