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

HRID 2199509Notes

Reaction equation

HRID 2199509 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

1-Cyclopropylsulphanyl-4-nitrobenzene in acetonitrile was admixed with iron(III) chloride and stirred at room temperature. Periodic acid was then added in portions. The mixture was stirred for 30 minutes and then added, with stirring, to a cooled, saturated sodium thiosulphate solution. Extraction was carried out with acetic ester (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified by means of chromatography (hexane/acetic ester 1:1) (yield: 76%).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. additionadded
  3. extractionExtraction
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue obtained
  8. customwas purified by means of chromatography (hexane/acetic ester 1:1) (yield: 76%)

Sources & evidence

ORD record
ord-e4c157c202d54a9394c65bbcea42921b
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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