Phosphorus pentachloride → 4'-Chloro-2,2':6',2''-terpyridine

HRID 1373378

Reaktionsgleichung

Reaktionsgleichung von HRID 1373378
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][C:11](=O)[CH:12]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21]>P(Cl)(Cl)(Cl)=O>[Cl:21][C:11]1[CH:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:10]=1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 6193532,6-Bis(2-pyridyl)-4(1H)-pyridone

Produkt 1

HCID 6677484'-Chloro-2,2':6',2''-terpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A mixture of 3.99 g (16 mmol) of 1′H-[2,2′;6′,2″]terpyridin-4′-one (L1) and 8.0 g (38 mmol) of phosphorus pentachloride is boiled at reflux in 200 ml of phosphorus oxychloride for sixteen hours. The mixture is allowed to cool and concentrated to dryness. 200 ml of ice-water are then added cautiously to the residue, and the solution is then adjusted to pH 9 with aqueous potassium hydroxide solution. Extracton is carried out three times using chloroform and the organic extracts are dried over sodium sulfate, filtered and concentrated. After recrystallisation from ethanol, 4′-chloro-[2,2′;6′,2″]terpyridine is obtained in the form of white needles. 1H-NMR (CDCl3, 360 MHz): 7.20–7.29 (m, 2H); 7.70–7.79 (tm, 2H); 8.37 (s, 2H); 8.47 (d, 2H; 7.6 Hz); 8.56–8.63 (dm, 2H).

Aufarbeitung

  1. temperatureto cool
  2. concentrationconcentrated to dryness
  3. addition200 ml of ice-water are then added cautiously to the residue
  4. dry with materialthe organic extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter recrystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3653ddffd74140168f7cc0c3dd0b06fe
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07161005B2

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