Hydrochloric Acid → HCID 178515422, Verbindung

HRID 1112521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1112521
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]([C:11](=[CH:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:12](OCC)=[O:13])#[N:10].Cl>O.O1CCCC1>[NH:5]1[C:9]([C:11]2[C:12](=[O:13])[N:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]3=[N:18][CH:17]=2)=[N:10][N:7]=[N:6]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 728730Ethyl 2-cyano-3-(2-pyridylamino)acrylateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 178515422HCID 178515422, VerbindungAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Aluminum chloride (0.74 g., 5.56 mmoles) was carefully added to tetrahydrofuran (33 ml.) at -20°. Sodium azide (1.08 g., 16.6 mmoles) was then added and the mixture heated under reflux for 30 minutes. After the addition of ethyl 2-cyano-3-(2-pyridylamino)acrylate (1.0 g., 4.6 mmoles) the mixture was again heated under reflux for 18 hours. The mixture was cooled in an ice bath, treated with water (170 ml.) and acidified to pH 2 with 6N hydrochloric acid. The resulting suspension was stirred with cooling for 2 hours and then filtered. The collected solid was recrystallized from N,N-dimethylformamide to give the title compound (0.38 g., 38.5%), m.p. 308°-309° (decomp).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturewas again heated
  4. temperatureunder reflux for 18 hours
  5. temperatureThe mixture was cooled in an ice bath
  6. temperaturewith cooling for 2 hours
  7. filtrationfiltered
  8. customThe collected solid was recrystallized from N,N-dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-bc6aa2ef044b43d298d8ab06fb3b7b6c
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04122274

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