Sodium Azide → HCID 178426257, Verbindung

HRID 1112529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1112529
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]([C:11](=[CH:17][NH:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10]>O1CCCC1>[CH3:25][C:24]1[C:19]2=[N:18][CH:17]=[C:11]([C:9]3[NH:10][N:7]=[N:6][N:5]=3)[C:12](=[O:13])[N:20]2[CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 3673519HCID 3673519, VerbindungHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 178426257HCID 178426257, VerbindungAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Aluminum chloride (3.51 g., 0.0263 mole) was added to cold (-30°) tetrahydrofuran (180 ml.). Sodium azide (5.12 g., 0.0788 mole) was added and the mixture heated under reflux for 30 minutes. The mixture was cooled to 5°. Ethyl 2-cyano-3-(3-methyl-2-pyridylamino)acrylate (5.0 g., 0.0216 mole) was added and the mixture heated under reflux for 18 hours. The tetrahydrofuran was removed under reduced pressure. The residue was treated with ice water (100 ml.) and acidified to pH 3 with 6N hydrochloric acid. The mixture was filtered and the collected solid recrystallized from N,N-dimethylformamide to give the title compound (2.5 g., 50.7%), m.p. 310°-311° (decomp).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe mixture was cooled to 5°
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 18 hours
  6. customThe tetrahydrofuran was removed under reduced pressure
  7. additionThe residue was treated with ice water (100 ml.)
  8. filtrationThe mixture was filtered
  9. customthe collected solid recrystallized from N,N-dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-dafe21e0e1504e22a940172d35ad4154
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04122274

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