4-(Cyanomethyl)benzoyl chloride → 2-(4-Cyanomethylphenyl)oxazolo[5,4-b]pyridine

HRID 259570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259570
[NH2:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=O)=[CH:14][CH:13]=1)#[N:10]>N1C=CC=CC=1>[C:9]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]2[O:8][C:3]3[C:2]([N:1]=2)=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:14][CH:13]=1)#[N:10]

Komponenten

4

Edukt 2

HCID 128039484-(Cyanomethyl)benzoyl chlorideHCID 178418824HCID 178418824, Verbindung

Produkt 1

HCID 227547692-(4-Cyanomethylphenyl)oxazolo[5,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Ten grams of 4-(cyanomethyl)benzoic acid is refluxed in 70 mls. of thionyl chloride for four hours. The solvents are removed leaving a residue of 4-cyanomethylbenzoyl chloride. To a solution of 5.5 g. of 3-amino-2-hydroxy pyridine in cold pyridine there is added slowly, with cooling, 8 g. of 4-cyanomethyl benzoyl chloride. The mixture is allowed to come to room temperature and stirred overnight. The mixture is added to 300 ml. of ice and the solid amide separated by filtration and recrystallized from methanol. A mixture of 3 g. of the above amide in 50 mls. of phosphorus oxychloride is heated under reflux for 5 hours. The solvents are removed in vacuo and the residue is crystallized from ethyl acetate to give 2-(4-cyanomethylphenyl)oxazolo[5,4-b]pyridine.

Aufarbeitung

  1. temperaturewith cooling
  2. customto come to room temperature
  3. additionThe mixture is added to 300 ml
  4. customof ice and the solid amide separated by filtration
  5. customrecrystallized from methanol
  6. additionA mixture of 3 g
  7. temperatureof phosphorus oxychloride is heated
  8. temperatureunder reflux for 5 hours
  9. customThe solvents are removed in vacuo
  10. customthe residue is crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4c0e6e978e7f41f98157cc6d2251df65
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04038396

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