tert-Butylhydrazine monohydrochloride → 2-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

HRID 381922

Reaktionsgleichung

Reaktionsgleichung von HRID 381922
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Cl:5])/[Cl:3].Cl.[C:11]([NH:15][NH2:16])([CH3:14])([CH3:13])[CH3:12]>CO>[C:11]([N:15]1[C:6](=[O:7])[C:4]([Cl:5])=[C:2]([Cl:3])[CH:1]=[N:16]1)([CH3:14])([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 2771871Mucochloric Acid

Produkt 1

HCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of mucochloric acid (33.8 g, 200 mmol) and tert.-butylhydrazine hydrochloride (24.9 g, 200 mmol) in methanol (400 mL) was stirred at reflux overnight. Methanol was removed in vacuo and the residue was partitioned between ether and water. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, 100% hexanes). Product-containing fractions were combined and the title compound was crystallized from ether/hexanes (yield: 10.0 g, 22.6%). mp 63-64° C. 1H NMR (300 MHz, CDCl3) δ 1.65 (s, 9H), 7.73 (s, 1H). MS (DCI/NH3) m/z 221 (M+H)+, 238 (M+NH4)+.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customMethanol was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography (silica gel, 100% hexanes)
  8. customthe title compound was crystallized from ether/hexanes (yield: 10.0 g, 22.6%)

Quellen und Nachweise

ORD-Eintrag
ord-897d36f9f0804f8eb20208ec60bbddc0
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307047B1

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