Sulfuric Acid → S-Methyl-S-(4-nitrophenyl)sulfoximine

HRID 238130

Reaktionsgleichung

Reaktionsgleichung von HRID 238130
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[N-:13]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([S:2]([CH3:1])(=[NH:13])=[O:3])=[CH:9][CH:8]=1)([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 3058821-(Methylsulfinyl)-4-nitrobenzene

Produkt 1

HCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

23.65 g (127.7 mmol) (RS)-1-(methylsulfinyl)-4-nitrobenzene in 130 ml chloroform are treated with 9.32 g (143.4 mmol) sodium azide. The mixture is slowly treated with 32.4 ml of concentrated sulfuric acid at 0° C. and then slowly heated to 45° C. After 16 hrs, the mixture is cooled to room temperature, treated with ice-water and extracted with chloroform. This organic phase is discarded. The aqueous phase is basified with 2N NaOH solution and extracted with DCM. The combined organic phases are washed with saturated NaCl solution, dried (Na2SO4), filtered and concentrated. 17.17 g (88.4 mmol, corresponding to 63% of theor.) of the product is obtained.

Aufarbeitung

  1. temperaturethe mixture is cooled to room temperature
  2. extractionextracted with chloroform
  3. extractionextracted with DCM
  4. washThe combined organic phases are washed with saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom17.17 g (88.4 mmol, corresponding to 63% of theor.) of the product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-e5184443c95e4597aee42f9b62f25dad
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642611B2

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