Phosphorus oxychloride → 5,7-dichloro-4H-imidazo[4,5-b]pyridine

HRID 868501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868501
[Cl:1][C:2]1[CH:7]=[CH:6][N+:5]([O-])=[C:4]2[NH:9][CH:10]=[N:11][C:3]=12.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[N:5]=[C:4]2[NH:9][CH:10]=[N:11][C:3]2=[C:2]([Cl:1])[CH:7]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178526259HCID 178526259, Verbindung

Produkt 1

HCID 1784781755,7-dichloro-4H-imidazo[4,5-b]pyridine

Versuchsvorschrift

7-Chloro-3H-imidazo[4,5-b]pyridine-4-oxide (15 g, 88.5 mMol) and 300 mL phosphorus oxychloride were heated at 110° C. under a nitrogen atmosphere. After 4 hours the excess phosphorus oxychloride was removed in vacuo. The residue was dissolved in water and the solution was neutralized by the addition of aqueous ammonium hydroxide. The suspension was cooled and the solid isolated. After drying, the product, 5,7-dichloro-3H-imidazo[4,5-b]pyridine, weighed 10.5 g (54.5 mMol, 61.6%); m.p. 263° C.; NMR (DMSO-d6): 8.58 δ (s, 1H, H2); 7.58 (s, 1H, H5).

Aufarbeitung

  1. customAfter 4 hours the excess phosphorus oxychloride was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. additionthe solution was neutralized by the addition of aqueous ammonium hydroxide
  4. temperatureThe suspension was cooled
  5. customthe solid isolated
  6. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-3759ad3fffb543f6968f4c211669f3ac
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04780452

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