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

HRID 329775

Reaktionsgleichung

Reaktionsgleichung von HRID 329775
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>[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

6

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 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

To a 500 ml, 3-neck, round bottom flask containing a cold (0° C.) slurry of 46.26 g (0.5 mol) of aminoacetonitrile hydrochloride and 32.74 ml (0.2 mol) of diethyl fumarate in 200 ml of ethyl acetate, were added dropwise, over one hour, an aqueous solution of sodium nitrite (34.5 g of sodium nitrite dissolved in 90 ml of water). The temperature of the reaction mixture was maintained between 0° C. and 5° C. during nitrite addition and 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 title compound 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-83a2a8f18d74417bba394f8dbc005b17
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892956

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