Hydrochloric Acid → 3,4-diethyl 1H-pyrazole-3,4-dicarboxylate

HRID 908210

Reaktionsgleichung

Reaktionsgleichung von HRID 908210
Cl.O.[NH2:3]N.Cl.[CH2:6]([O:8][C:9](=[O:22])[C:10](=[CH:18][N:19](C)C)[C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:7]>C(O)C>[CH2:15]([O:14][C:12]([C:11]1[NH:3][N:19]=[CH:18][C:10]=1[C:9]([O:8][CH2:6][CH3:7])=[O:22])=[O:13])[CH3:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 22250811Hydrazine monohydrate hydrochlorideHCID 72733183Diethyl 2-((dimethylamino)methylene)-3-oxosuccinate

Produkt 1

HCID 145056993,4-diethyl 1H-pyrazole-3,4-dicarboxylateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Under an atmosphere of argon, hydrazine monohydrate hydrochloride (1.91 g, 28 mmol) and HCl (36.5% in water, 2.8 ml) were added to a solution of 2-dimethylaminomethylene-3-oxo-succinic acid diethyl ester (6.8 g, 28 mmol, obtained by the method of Hanzlowsky et al., J. Heterocyclic Chem. 2003, 40(3), 487-498) in ethanol (100 ml). The mixture was heated to 60° C. (3 h). The solvent was evaporated, and the residue was taken up in dichloromethane and washed (water). The organic layer was dried (Na2SO4), the solvent was evaporated and the title compound (1.81 mg, 31%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=383.3 [M+H+].

Aufarbeitung

  1. customobtained by the method of Hanzlowsky et al., J
  2. customThe solvent was evaporated
  3. washwashed (water)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c34a6319f2844cd1a5dc72ff0ff35cdc
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017604B2

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