Potassium Carbonate → HCID 59739569, compound

HRID 1192967Notes

Reaction equation

HRID 1192967 reaction equation
N[C:2](N)=S.C[C:6]1([CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1)[CH2:7]Br.C[S:15]([C:18]1[CH2:22][C:21]([CH3:24])([CH3:23])[O:20][N:19]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:23][C:21]1([CH3:24])[O:20][N:19]=[C:18]([S:15][CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:2])[CH2:22]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 68534582HCID 68534582, compound

Product 1

HCID 59739569HCID 59739569, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Thiourea (180 mg, 2.4 mmol) was added to a solution of 1-methyl benzyl bromide (0.3 ml, 2.2 mmol) in ethanol (10 ml) at room temperature. The mixture was heated under reflux for 5 hours. 3-Methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (420 mg, 2.4 mmol) and potassium carbonate (330 mg, 2.4 mmol) were added and the mixture was heated under reflux for 3 hours. The mixture was allowed to cool to room temperature, poured into water and the mixture extracted with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as a white solid (210 mg, 43% yield) which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hours
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8f59b009a025427bb80152c19c73b365
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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