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

HRID 1169708

Reaktionsgleichung

Reaktionsgleichung von HRID 1169708
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.I(O)(=O)(=O)=[O:13].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.[Fe](Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)=[O:13]

Komponenten

6

Edukt 3

HCID 24477Sodium ThiosulfateHCID 65185Metaperiodic acidHCID 961094-Nitrophenyl methyl sulfide

Produkt 1

HCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 25.00 g (147.8 mmol) 1-methylsulphanyl-4-nitro-benzene and 0.69 g (4.2 mmol) iron(III) chloride (anhydrous) in 120 ml acetonitrile is treated with 36.0 g (158.1 mmol) periodic acid and stirred at room temperature. At the start of heat evolution, the mixture is transiently cooled with an ice-bath, so that the temperature does not rise above 30° C. After the heat evolution has subsided, the mixture is stirred at room temperature for a further 10 mins. The mixture is poured into a solution of 150 g sodium thiosulphate in 1000 ml ice-water and then extracted with DCM. The combined organic phases are washed with saturated NaCl solution, dried (Na2SO4), filtered and concentrated. The remaining residue is recrystallised from toluene. 23.6 g (128.0 mmol, corresponding to 86% of theor.) of the product is obtained.

Aufarbeitung

  1. temperatureAt the start of heat evolution, the mixture is transiently cooled with an ice-bath, so that the temperature
  2. customdoes not rise above 30° C
  3. stirringthe mixture is stirred at room temperature for a further 10 mins
  4. extractionextracted with DCM
  5. washThe combined organic phases are washed with saturated NaCl solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe remaining residue is recrystallised from toluene
  10. custom23.6 g (128.0 mmol, corresponding to 86% of theor.) of the product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-28910b1747254515a0eb5f5d7c5bf943
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825128B2

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