Potassium Carbonate → HCID 86688393, Verbindung

HRID 1488323

Reaktionsgleichung

Reaktionsgleichung von HRID 1488323
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4](=O)[CH2:3][CH2:2]1.[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-:27].[K+].[K+].CN1C(=O)CCC1>[Cl-].[Na+].O.C(OC(=O)C)C>[C:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:12]1[C:13]2[C:1](=[O:27])[CH2:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)([CH3:18])([CH3:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 9291301,2,3,9-Tetrahydro-4H-carbazol-4-one2×HCID 119590501-Bromo-2-tert-butylbenzene

Produkt 1

HCID 86688393HCID 86688393, VerbindungAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

In a 500 ml two-neck flask, 1,2,3,4-tetrahydro-9H-carbazole-4-one (Compound E, 20 g), t-butyl bromobenzene (60 g), potassium carbonate (43 g), Cu powder (2.1 g), and NMP (70 ml) were mixed and stirred. The reaction mixture was refluxed and stirred for 24 to 30 hours in a state in which the temperature was raised. When the reaction was completed, the reactant was cooled at room temperature, and then the reactant was mixed with ethylacetate (500 ml) and brine (500 ml) and strongly stirred. Floating materials was filtered and removed using celite, and the organic layer was separated. The water layer was extracted using ethylacetate, and the organic layer was collected and dried over magnesium sulfate. The organic layer was concentrated, and the residual was purified using a column chromatography, thereby obtaining 13 g of N-(t-butylphenyl) carbazolone (Compound F).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed
  2. stirringstirred for 24 to 30 hours in a state in which the temperature
  3. temperaturewas raised
  4. stirringstrongly stirred
  5. filtrationFloating materials was filtered
  6. customremoved
  7. customthe organic layer was separated
  8. extractionThe water layer was extracted
  9. customthe organic layer was collected
  10. dry with materialdried over magnesium sulfate
  11. concentrationThe organic layer was concentrated
  12. customthe residual was purified

Quellen und Nachweise

ORD-Eintrag
ord-cc0dbb89b67c4b899eba41d833ca6efc
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09431616B2

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