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

HRID 1416004Notes

Reaction equation

HRID 1416004 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 aqueous 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 dried 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. customthe mixture was reacted on an oil bath at 130° C. for 3 hours during which time the mixture
  2. concentrationwas concentrated
  3. temperatureThe reaction mixture was cooled
  4. additiona saturated aqueous sodium bicarbonate solution was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over magnesium sulfate
  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-55f5bdb93b0d43bbb09fb75f43d92228
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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