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

HRID 238129

반응식

HRID 238129 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 3058821-(Methylsulfinyl)-4-nitrobenzene

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52488375d7e24f31be2d2617bf4cd6b3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642611B2

연결된 노트

불러오는 중…