Dimethyl Sulfoxide → HCID 59829809, compound

HRID 1947217Notes

Reaction equation

HRID 1947217 reaction equation
[OH-:1].[Na+].CS(C)=O.[CH:7]([N:10]1[C:14](S(C)(=O)=O)=[N:13][N:12]=[C:11]1[C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[C:22]([O:28][CH2:29][O:30][CH3:31])=[CH:21][C:20]=1[O:32][CH2:33][O:34][CH3:35])([CH3:9])[CH3:8]>O>[CH:7]([N:10]1[C:11]([C:19]2[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[C:22]([O:28][CH2:29][O:30][CH3:31])=[CH:21][C:20]=2[O:32][CH2:33][O:34][CH3:35])=[N:12][NH:13][C:14]1=[O:1])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 59829848HCID 59829848, compound

Product 1

HCID 59829809HCID 59829809, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

At room temperature, aqueous sodium hydroxide (1.0 M aqueous solution, 9 mL) was added to a dimethylsulfoxide (11 mL) solution of 4-isopropyl-3-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-5-methyl sulfonyl-4H-[1,2,4]triazole (F63-05, 1.63 g, 3.82 mmol). The mixture was heated at 90-100° C. for 12 hours while stirring. After returning to room temperature, water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed twice with water and then with saturated sodium chloride solution. After drying the extract over anhydrous sodium, sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain white solids. After suspension purification by diethyl ether, the solids obtained by filtration were dried under reduced pressure to obtain 4-isopropyl-5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-one (F63-06, white solids, 1.09 g, 78%).

Workup

  1. customAfter returning to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed twice with water
  4. customAfter drying the
  5. extractionextract over anhydrous sodium, sodium sulfate
  6. customwas removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain white solids
  9. customAfter suspension purification by diethyl ether
  10. customthe solids obtained by filtration
  11. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-441b717dd15d4898a74cd9cacde1379d
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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