Dimethylformamide → 9-ethyl-9H-carbazole-3,6-dicarbaldehyde

HRID 1393887

Reaktionsgleichung

Reaktionsgleichung von HRID 1393887
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[CH2:11]([N:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12].[C:26]([O-])(=[O:28])C.[Na+]>O>[CH2:11]([N:13]1[C:25]2[CH:24]=[CH:23][C:22]([CH:26]=[O:28])=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[C:17]([CH:3]=[O:4])[CH:18]=2)[CH3:12]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6836N-ethyl carbazoleHCID 24813Phosphorus oxychloride3×HCID 517045Sodium Acetate

Produkt 1

HCID 37166759-ethyl-9H-carbazole-3,6-dicarbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Dimethylformamide (DMF) (271 ml, 3.5 mol, from Aldrich Chemicals, Milwaukee, Wis.) was added to a 1-liter, 3-neck round bottom flask equipped with a mechanical stirrer, a thermometer, and a dropping funnel. The flask and its content were cooled on a salt/ice bath. When the temperature of the solution inside the flask reached 0° C., phosphorus oxychloride (POCl3, 326 ml, 3.5 mol, from Aldrich Chemicals, Milwaukee, Wis.) was added slowly using a dropping funnel. During the addition of POCl3, the temperature inside the flask was kept at or below 5° C. After completing the addition of POCl3, the reaction mixture was allowed to warm to room temperature. 9-Ethylcarbazole (97 g, 0.5 mole, from Aldrich chemicals, Milwaukee, Wis.) was added and the flask was kept at 90° C. for 24 hours using a heating mantle. Then, the reaction mixture was cooled to room temperature. The cooled reaction mixture was added slowly to a 4.5 liter beaker containing a solution of 820 g sodium acetate dissolved in 2 liters of water. The beaker was stirred and cooled on an ice bath for 3 hours. The brownish solid obtained was filtered and washed repeatedly with water and, subsequently, with a small amount of ethanol (50 ml). The resulting product, 9-ethyl-3,6-carbazoledicarbaldehyde, was recrystallized once from a mixture of tetrahydrofuran and isopropanol and dried under vacuum in an oven heated at 50° C. for 6 hours. The yield was 65 g (52%).

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. temperatureThe flask and its content were cooled on a salt/ice bath
  3. customreached 0° C.
  4. custombelow 5° C
  5. temperatureThen, the reaction mixture was cooled to room temperature
  6. customThe cooled reaction mixture
  7. additionwas added slowly to a 4.5 liter beaker
  8. temperaturecooled on an ice bath for 3 hours
  9. customThe brownish solid obtained
  10. filtrationwas filtered
  11. washwashed repeatedly with water
  12. customThe resulting product, 9-ethyl-3,6-carbazoledicarbaldehyde, was recrystallized once from a mixture of tetrahydrofuran and isopropanol
  13. customdried under vacuum in an oven
  14. temperatureheated at 50° C. for 6 hours

Quellen und Nachweise

ORD-Eintrag
ord-53e9157056c64632aa5e95863e44f16f
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348112B2

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