Diphenyl sulfoxide → HCID 23054313, compound

HRID 1172033Notes

Reaction equation

HRID 1172033 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][C:16]1[CH:29]=[CH:28][C:27]2[S:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:30])[C:18]=2[CH:17]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[F:46][P-:47]([F:52])([F:51])([F:50])([F:49])[F:48].[K+]>O.ClCCl>[F:46][P-:47]([F:52])([F:51])([F:50])([F:49])[F:48].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:22]2[CH:23]=[CH:24][C:25]3[S:26][C:27]4[C:18](=[CH:17][C:16]([Cl:15])=[CH:29][CH:28]=4)[C:19](=[O:30])[C:20]=3[CH:21]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 13679Diphenyl sulfoxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 6188482-ChlorothioxanthoneHCID 23688904Potassium hexafluorophosphate2×

Product 1

HCID 23054313HCID 23054313, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent3×

Procedure

To 320 ml of dichloromethane were suspended 20.2 g (0.1 mol) of diphenylsulfoxide and 24.6 g (0.1 mol) of 2-chlorothioxanthene-9-one, and 28.2 g (0.1 mol) of trifluoromethanesulfonic anhydride was added dropwise thereto at −70 to −60° C., followed by gradually warming to room temperature and reacting with stirring for 3 hours. After completion of the reaction, the obtained reaction solution was washed with water (320 ml×5 times) and 18.4 g (0.1 mol) of potassium hexafluorophosphate and 200 ml of water were added to the obtained dichloromethane layer, followed by stirring at room temperature for 2 hours and fractionating the solution. Then, 9.2 g (0.05 mol) of potassium hexafluorophosphate and 100 ml of water were further added to the obtained dichloromethane layer, followed by stirring at room temperature for 2 hours and fractionating the solution. Then the obtained dichloromethane layer was washed with 200 ml of water and concentrated to dryness under reduced pressure. The obtained crude product was purified by column chromatography to obtain 4.0 g of objective substance as pale yellow glassy substance (yield: 7%).

Workup

  1. additionwas added dropwise
  2. customat −70 to −60° C.
  3. customAfter completion of the reaction
  4. customthe obtained reaction solution
  5. stirringby stirring at room temperature for 2 hours
  6. stirringby stirring at room temperature for 2 hours
  7. washThen the obtained dichloromethane layer was washed with 200 ml of water
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by column chromatography
  11. customto obtain 4.0 g of objective substance as pale yellow glassy substance (yield: 7%)

Sources & evidence

ORD record
ord-afac1c884c444ec491531d0796bb4ed1
Source dataset
uspto-grants-2010_11
Patent number
US07833691B2

Reaction notes

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