Phosphorus oxychloride → HCID 86649502, Verbindung

HRID 1037508

Reaktionsgleichung

Reaktionsgleichung von HRID 1037508
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)Cl.CN([CH:41]=[O:42])C.O=P(Cl)(Cl)Cl.[OH-].[K+].O>ClCCCl.CN(C=O)C>[CH:10]1[C:11]2[N:12]([C:14]3[N:15]=[C:16]([N:20]4[C:32]5[CH:31]=[CH:30][C:29]([CH:41]=[O:42])=[CH:28][C:27]=5[C:26]5[C:21]4=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:17]=[CH:18][CH:19]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 24813Phosphorus oxychlorideHCID 13765457DMF Phosphorus oxychloride3×HCID 23062165HCID 23062165, VerbindungHCID 23719240Potassium hydroxide monohydrate

Produkt 1

HCID 86649502HCID 86649502, VerbindungAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2,6-di(carbazol-9-yl)pyridine, prepared above in step 1, (10.0 g, 24.4 mmol) in 1,2-dichloroethane (80.0 ml) was slowly added POCl3/DMF (32.0 g/16.0 g). POCl3/DMF was made by the addition of POCl3 into DMF at 0° C. at room temperature under nitrogen atmosphere and stirring. After the addition of POCl3/DMF, the reaction mixture was heated to 110° C. and kept at this temperature for 72 hours. After cooling, the reaction mixture was slowly added into an ice-bath cooled KOH water solution (500.0 ml of water with 100 g of KOH). After addition, the reaction mixture was stirred for 60 minutes. The water solution was extracted with ethyl acetate (3×100 ml). The organic extracted solution was washed with water until a pH=7 was obtained. The removal of solvent, crude product was purified by silica gel column with dichloromethane:hexanes:ethyl acetate (5:4.5:0.5) as the solvent mixture. After removal of the solvent mixture, the product was recrystallized from THF/water to give 4.3 g (40.3%) of pure product.

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthe reaction mixture was slowly added into an ice-bath
  3. additionAfter addition
  4. stirringthe reaction mixture was stirred for 60 minutes
  5. extractionThe water solution was extracted with ethyl acetate (3×100 ml)
  6. washThe organic extracted solution was washed with water until a pH=7
  7. customwas obtained
  8. customThe removal of solvent, crude product
  9. customwas purified by silica gel column with dichloromethane:hexanes:ethyl acetate (5:4.5:0.5) as the solvent mixture
  10. customAfter removal of the solvent mixture
  11. customthe product was recrystallized from THF/water

Quellen und Nachweise

ORD-Eintrag
ord-96cb633c622a41e799f0fc19dd463b3a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546505B2

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