Sodium Thiosulfate → 1-(Cyclopropanesulfinyl)-4-nitrobenzene

HRID 1027843Notes

Reaction equation

HRID 1027843 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.I(O)(=O)(=O)=[O:15].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.[Fe](Cl)(Cl)Cl>[CH:1]1([S:4]([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 65185Metaperiodic acidHCID 59252683Cyclopropyl(4-nitrophenyl)sulfane

Product 1

HCID 595508341-(Cyclopropanesulfinyl)-4-nitrobenzeneYield 76%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6342AcetonitrileSolvent

Procedure

179 mg (1.11 mmol) of iron(III) chloride was added to a mixture of 7.2 g (36.88 mmol) of 1-cyclopropylsulfanyl-4-nitrobenzene in 140 ml acetonitrile and it was stirred for 15 minutes at room temperature. Then 9.25 g (40.57 mmol) of periodic acid was added in portions at 25° C. The mixture was stirred for 30 minutes and then added, while stirring, to a cooled saturated sodium thiosulfate solution. It was then extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 1:1). 5.93 g (28.07 mmol; yield: 76%) of the product was obtained.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. additionadded
  3. extractionIt was then extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue obtained
  8. customwas purified chromatographically (hexane/ethyl acetate 1:1)
  9. custom5.93 g (28.07 mmol; yield: 76%) of the product was obtained

Sources & evidence

ORD record
ord-c434d8edf55743e1acfdfb001b93311e
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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