Hydrochloric Acid → (5-(3,5-Difluorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanol

HRID 1857712Notes

Reaction equation

HRID 1857712 reaction equation
C([O:8][CH2:9][C:10]1[N:11]([CH2:27][CH3:28])[C:12]([S:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)C1C=CC=CC=1.Cl>C(O)C>[F:25][C:23]1[CH:24]=[C:19]([S:18][C:12]2[N:11]([CH2:27][CH3:28])[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:16])[CH3:17])[CH:20]=[C:21]([F:26])[CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22130057HCID 22130057, compound

Product 1

HCID 473945(5-(3,5-Difluorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanolYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 5 ml of ethanol was dissolved 300 mg (0.75 mmol) of 2-benzyloxymethyl-5-(3,5-difluorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole (17z), followed by addition of 5N--HCl (10 ml) at room temperature with stirring and the mixture was reacted on an oil bath at 130° C. for 3 hours during which time the mixture was concentrated. The reaction mixture was cooled, and a saturated aqeous sodium bicarbonate solution was added to be weakly alkali. The mixture was extracted with ethyl acetate, the ethyl acetate layer was washed with water and cried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residual oil was crystallized from n-hexane, and filtered to give 160 mg of Compound I-36 (yield 68%). mp 102-104° C.

Workup

  1. additionfollowed by addition of 5N
  2. customthe mixture was reacted on an oil bath at 130° C. for 3 hours during which time the mixture
  3. concentrationwas concentrated
  4. temperatureThe reaction mixture was cooled
  5. additiona saturated aqeous sodium bicarbonate solution was added
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe ethyl acetate layer was washed with water
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residual oil was crystallized from n-hexane
  10. filtrationfiltered

Sources & evidence

ORD record
ord-d0506ee3aea54e958c9b9523f57c8717
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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