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

HRID 1169708ノート

反応式

HRID 1169708 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 3058821-(Methylsulfinyl)-4-nitrobenzene

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28910b1747254515a0eb5f5d7c5bf943
出典データセット
uspto-grants-2010_11
特許番号
US07825128B2

反応ノート

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