Ethyl Acetate → HCID 17838729, compound

HRID 1293128Notes

Reaction equation

HRID 1293128 reaction equation
CC1C=C(C)C=C(C)C=1S[C:11]1[N:15]=[CH:14][N:13]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[N:12]=1.ClC1[CH:27]=[CH:26][CH:25]=[C:24]([C:28](OO)=O)[CH:23]=1.[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+].[C:39](=O)([O-])[O-].[K+].[K+].C(O[CH2:49][CH3:50])(=O)C>>[CH3:39][C:26]1[CH:25]=[C:24]([CH3:28])[CH:23]=[C:49]([CH3:50])[C:27]=1[S:32]([C:11]1[N:15]=[CH:14][N:13]([C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[N:12]=1)(=[O:36])=[O:34]

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 17838728HCID 17838728, compound

Product 1

HCID 17838729HCID 17838729, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-(2,4,6-trimethylphenyl)thio-1-dimethylcarbamoyl-1H-1,2,4-triazole (Example 32) (226 mg) and ethyl acetate (1 ml) was added m-chloroperbenzoic acid (360 mg), and the reaction mixture was heated and stirred for 4 hours on an oil bath at 60° C. To the reaction solution were added 1 M aqueous sodium thiosulfate solution (0.1 ml) and 5 M aqueous potassium carbonate solution (0.25 ml), and the mixture was extracted with ethyl acetate-water. The organic layer was washed with saturated aqueous sodium chloride solution and concentrated. The residue was dissolved in ethyl acetate with heating. The solution was filtered through a small amount silica gel, which was washed with ethyl acetate, and concentrated under reduced pressure. The residue was crystallized in ethyl acetate-hexane to yield the title compound (178 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. extractionthe mixture was extracted with ethyl acetate-water
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. temperaturewith heating
  7. filtrationThe solution was filtered through a small amount silica gel, which
  8. washwas washed with ethyl acetate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was crystallized in ethyl acetate-hexane

Sources & evidence

ORD record
ord-6c0ce702aedc41dcbe17ad947367ceae
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Reaction notes

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