Pyridazine → N-aminopyridazinium sulfate

HRID 392857

Reaktionsgleichung

Reaktionsgleichung von HRID 392857
[NH2:1][O:2][S:3]([OH:6])(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>O>[S:3]([O-:6])([O-:5])(=[O:4])=[O:2].[NH2:1][N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[NH2:1][N+:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Komponenten

5

Edukt 3

HCID 9259PyridazineHCID 11430Potassium CarbonateHCID 76284hydroxylamine-O-sulfonic acid

Produkt 1

HCID 69698706N-aminopyridazinium sulfate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of hydroxylamine-O-sulfonic acid (73.4 g) in water (80 mL) and a separate solution of potassium carbonate (65.5 g) in water (80 mL) were added concurrently dropwise to a solution of pyridazine (40.0 g) in water (120 mL) at 50° C., maintaining a reaction mixture pH of 3.5-4.0. The reaction mixture was then heated at 40° C. for 2 hours to give a solution of N-aminopyridazinium sulfate, which was subsequently cooled to 20° C. and filtered. The filtrate was added dropwise to a solution of potassium hexafluorophosphate (91.9 g) in water (460 mL) at 50° C. The resulting suspension was slowly cooled to 5° C. over a 2 hour period, stirred for 30 minutes and the product isolated by filtration. The filtercake was washed portionwise with water (320 mL) and the product dried in vacuo at 40° C. to give the title compound as a white crystalline solid (69.9 g, 58%).

Quellen und Nachweise

ORD-Eintrag
ord-7fc5ab3d86a64735ad38223e8198a70f
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06803463B2

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