Dimethyl Sulfoxide → 4-(3-Methyl-4-nitrophenyl)morpholine

HRID 912329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912329
CS(C)=O.F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH3:15])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[CH3:15][C:8]1[CH:7]=[C:6]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Produkt 1

HCID 112645284-(3-Methyl-4-nitrophenyl)morpholineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a DMSO solution (8 ml) of 4-fluoro-2-methyl-1-nitro-benzene (500 mg), potassium carbonate (668 mg) and morpholine (0.42 ml) were added, followed by stirring at 80° C. for 18 hours. This was cooled to room temperature, and water (30 ml) was added, followed by extraction with ethyl acetate (50 ml×2). The organic layer was washed with saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate. After the magnesium sulfate was filtered off, the solvent was distilled off under reduced pressure, to obtain the desired compound as a yellow solid (680 mg, 95%).

Aufarbeitung

  1. temperatureThis was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate (50 ml×2)
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialby drying over magnesium sulfate
  5. filtrationAfter the magnesium sulfate was filtered off
  6. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c96970a1d30d412fbad3d297832e48a9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022205B2

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