Hydrochloric Acid → 4-(tert-Butyl)-3-chloro-6-hydrazinylpyridazine

HRID 2301334

Reaktionsgleichung

Reaktionsgleichung von HRID 2301334
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].O.[NH2:14][NH2:15].Cl>C(O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:14][NH2:15])=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 898464-tert-Butyl-3,6-dichloropyridazine

Produkt 1

HCID 229878864-(tert-Butyl)-3-chloro-6-hydrazinylpyridazineAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3,6-dichloro-4-(1,1-dimethylethyl)pyridazine (2.0 g, 9.76 mmol) in ethanol (30 ml) was added hydrazine hydrate (0.34 ml, 10.9 mmol) dropwise. The reaction mixture was heated at reflux for 18 h under an atmosphere of nitrogen. The solvent was removed under high vacuum to leave a residue to which was added 5N hydrochloric acid (50 ml). The solution obtained was washed with dichloromethane (20 ml) and the aqueous layer was poured on to a mixture of ice and aqueous ammonia. The resultant solid was collected by filtration and dried under vacuum to yield the title compound (1.2 g). Data for the title compound: 1H NMR (360 MHz, DMSO) δ1.39 (3H, t, J=7.3 Hz), 4.35 (2H), 7.07 (1H, s), 8.07 (1H, s); MS (ES+) m/e 201, 203 [MH]+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h under an atmosphere of nitrogen
  3. customThe solvent was removed under high vacuum
  4. customto leave a residue to which
  5. customThe solution obtained
  6. washwas washed with dichloromethane (20 ml)
  7. additionthe aqueous layer was poured on to a mixture of ice and aqueous ammonia
  8. filtrationThe resultant solid was collected by filtration
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2e2d0de0385d4b068fccc0379568d93a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500828B1

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