(3-(Trifluoromethyl)phenyl)hydrazine → 4,5-Dibromo-2-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one

HRID 1902832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1902832
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Br:5])/[Br:3].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([NH:18][NH2:19])[CH:15]=[CH:16][CH:17]=1>C(O)C>[F:10][C:11]([F:20])([F:21])[C:12]1[CH:13]=[C:14]([N:18]2[C:6](=[O:7])[C:4]([Br:5])=[C:2]([Br:3])[CH:1]=[N:19]2)[CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 3033972Mucobromic Acid

Produkt 1

HCID 167793014,5-Dibromo-2-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-oneAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 21.4 grams of mucobromic acid and 13.3 grams of 3-trifluoromethylphenyl hydrazine in 60 milliliters of ethanol was stirred for about 10 minutes. The ethanol was removed by evaporation under reduced pressure, and then 40 milliliters each of glacial acetic acid and acetic anhydride were added to the reaction vessel. The acidic reaction mixture was heated at reflux for 4 hours. The reaction solvent was removed by evaporation under reduced pressure whereupon a solid precipitate formed. The solid was purified by recrystallization from ethanol. A yield of 20.7 grams of 1-(3-trifluoromethylphenyl)-4,5-dibromo-1,6-dihydro-6-oxopyridazine was obtained.

Aufarbeitung

  1. customThe ethanol was removed by evaporation under reduced pressure
  2. addition40 milliliters each of glacial acetic acid and acetic anhydride were added to the reaction vessel
  3. temperatureThe acidic reaction mixture was heated
  4. temperatureat reflux for 4 hours
  5. customThe reaction solvent was removed by evaporation under reduced pressure whereupon a solid precipitate
  6. customformed
  7. customThe solid was purified by recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4912cb79dc0b4c9dbcf5dc2e40300929
Quelldatensatz
uspto-grants-1982_12
Patentnummer
US04366155

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