Dimethyl Sulfate → N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine

HRID 240557

Reaktionsgleichung

Reaktionsgleichung von HRID 240557
[OH-].[Na+].[CH3:3][C:4]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1.S(OC)(O[CH3:28])(=O)=O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>O.C1(C)C=CC=CC=1>[CH3:28][NH:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:4]=2[CH3:3])=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15]

Komponenten

7

Edukt 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphateHCID 866508954-(2-Methyl-4-nitrophenoxy)-2-nitrobenzenamine

Produkt 1

HCID 86650896N-methyl-4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of sodium hydroxide (10.2 g in 10.5 mL water) was added toluene (15 mL), 4-(2-methyl-4-nitrophenoxy)-2-nitrobenzenamine (2.00 g, 6.92 mmol), dimethyl sulfate (750 μL, 7.88 mmol) and tetrabutylammonium sulfate (0.277 g, 0.816 mmol). After stirring at room temperature, the cooled (0° C.) reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (100 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was chromatographed (dichloromethane) to provide the product (1.90 g, 91%).

Aufarbeitung

  1. temperaturethe cooled
  2. custom(0° C.) reaction mixture
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-84b6540a481e4829af7f3db48c89bdc2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648087B2

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