Nitrite → 5-Cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester

HRID 329776

Reaktionsgleichung

Reaktionsgleichung von HRID 329776
Cl.[NH2:2][CH2:3][C:4]#[N:5].[C:6]([O:15][CH2:16][CH3:17])(=[O:14])/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10].[N:18]([O-])=O.[Na+].N([O-])=O>C(OCC)(=O)C.O>[CH2:16]([O:15][C:6]([CH:7]1[CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]([C:3]#[N:2])[N:5]=[N:18]1)=[O:14])[CH3:17]

Komponenten

7

Edukt 4

HCID 946NitriteHCID 638144Diethyl fumarateHCID 11491918Aminoacetonitrile hydrochlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 147663655-Cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

To a one liter round bottom flask containing a cold (0° C.) slurry of 67.6 g (0.6756 mol) of aminoacetonitrile hydrochloride and 44.2 ml (0.2702 mol) of diethyl fumarate in 300 ml of ethyl acetate, were added dropwise, over one hour, an aqueous solution of 46.6 g (0.6756 mol) of sodium nitrite dissolved in 90 ml of water. The temperature of the reaction mixture was maintained at about 0° C. during the nitrite addition, then warmed to room temperature (24° C.) where the mixture was stirred for about 3 hours. The organic layer was separated from the aqueous layer and then stirred at room temperature overnight to provide a solution of 5-cyano-4,5-dihydro-3H-pyrazole-3,4-dicarboxylic acid diethyl ester dissolved in ethyl acetate.

Aufarbeitung

  1. additionwere added dropwise, over one hour
  2. customThe organic layer was separated from the aqueous layer
  3. stirringstirred at room temperature overnight

Quellen und Nachweise

ORD-Eintrag
ord-63a30eece6694620beea1f91faa4e8a3
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892956

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