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

HRID 640664

Reaction equation

HRID 640664 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

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. Extraction 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).

Workup

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

Sources & evidence

ORD record
ord-fb9ba4591b4a4305b522dcec802bb6fb
Source dataset
uspto-grants-2010_04
Patent number
US07692004B2

Linked notes

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