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

HRID 238129

Reaction equation

HRID 238129 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 25.0 g (147.8 mmol) 1-methylsulfanyl-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.

Workup

  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

Sources & evidence

ORD record
ord-52488375d7e24f31be2d2617bf4cd6b3
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Linked notes

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