4-Cyanopyridine → HCID 178419986, Verbindung

HRID 263122

Reaktionsgleichung

Reaktionsgleichung von HRID 263122
[Na].[N:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]([NH:18][NH2:19])=O>CO>[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)[NH:19][N:18]=1

Komponenten

5

Edukt 3

HCID 75064-CyanopyridineHCID 258796Pyrazine-2-Carboxylic Acid HydrazideHCID 5360545Sodium

Produkt 1

HCID 178419986HCID 178419986, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
260 °C

Versuchsvorschrift

Sodium (0.4 grams) is added to pyridine-4-carbonitrile (8.3 grams, 0.08 mole) in methanol, and the solution is allowed to stand 30 minutes at room temperature. A suspension of pyrazine carboxylic acid hydrazide (9.6 grams, 0.07 mole) in methanol (160 ml.) is added, and the resulting solution is heated at reflux for 30 minutes. After cooling, the intermediate acylamidrazone is collected by filtration. The acyclic intermediate is then heated at 260° C. for 15 minutes, after which the reaction is cooled to room temperature. Upon recrystallization from acetonitrile-water, 3-pyrazinyl-5-(4-pyridyl)-1,2,4-triazole is obtained, m.p. 251°-252.5° C.

Aufarbeitung

  1. additionis added
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling
  5. filtrationthe intermediate acylamidrazone is collected by filtration
  6. temperatureafter which the reaction is cooled to room temperature
  7. customUpon recrystallization from acetonitrile-water

Quellen und Nachweise

ORD-Eintrag
ord-2dd9c049b902440eb6c979fbf9c98166
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156085

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