1,4-Dibromobutane → Diethyl tetrahydropyridazine-1,2-dicarboxylate

HRID 363171

Reaktionsgleichung

Reaktionsgleichung von HRID 363171
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[C:7]([NH:12][NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:12]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][N:13]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

5

Edukt 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 777581,2-Hydrazinedicarboxylic acid, 1,2-diethyl ester

Produkt 1

HCID 281963Diethyl tetrahydropyridazine-1,2-dicarboxylateAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1,4-Dibromobutane (81.4 mL, 0.682 mol) is added over 1 hour to a mixture of 1,2-dicarbethoxyhydrazine (100 g, 0.568 mol) and potassium carbonate (158 g, 1.14 mol) in acetonitrile (600 mL). The resultant reaction mixture is refluxed for 6 hours, cooled to room temperature, and filtered. The filtrate is concentrated in vacuo to obtain a yellow liquid which is distilled under reduced pressure to give the title product as a colorless liquid (90.8 g, bp 115°-120° C. at 0.9 mm Hg).

Aufarbeitung

  1. customThe resultant reaction mixture
  2. temperatureis refluxed for 6 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto obtain a yellow liquid which
  6. distillationis distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b51149b8649147fdb79f888681899fc2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872253

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