Hydrazinecarboxylic acid, ethyl ester → 6-(p-Bromophenyl)-1,2,4-triazolo[4,3-b]pyridazin-3(2H)-one

HRID 462408

Reaktionsgleichung

Reaktionsgleichung von HRID 462408
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11](Cl)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15](OCC)(=[O:18])[NH:16][NH2:17]>C(O)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:15](=[O:18])[NH:16][N:17]=3)[N:13]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 64052553-(4-Bromophenyl)-6-chloropyridazine

Produkt 1

HCID 134245986-(p-Bromophenyl)-1,2,4-triazolo[4,3-b]pyridazin-3(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 2.69 g. of 6-(p-bromophenyl)-3-chloropyridazine (U.S. Pat. No. 4,092,311), 3.12 g. of ethyl carbazate and 50 ml. of n-butanol is heated at reflux for 16 hours, then cooled and filtered giving an orange solid which is saved. The filtrate is heated at reflux for 23 hours, then chilled in an ice bath and filtered giving more orange solid. The two crops are combined and recrystallized from dimethylformamide, giving 0.65 g. of the desired product as orange crystals, m.p. 348°-350° C. (dec.).

Aufarbeitung

  1. additionA mixture of 2.69 g
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customgiving an orange solid which
  6. temperatureThe filtrate is heated
  7. temperatureat reflux for 23 hours
  8. temperaturechilled in an ice bath
  9. filtrationfiltered
  10. customgiving more orange solid
  11. customrecrystallized from dimethylformamide
  12. customgiving 0.65 g

Quellen und Nachweise

ORD-Eintrag
ord-898f497980c34719baaee1bbc5ee6289
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04515791

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