Ethyl chloroformate → 2-Ethoxycarbonyloxyimino-2-cyanoacetic acid amide

HRID 1283750

Reaktionsgleichung

[Na].[OH:2][N:3]=[C:4]([C:8]#[N:9])[C:5]([NH2:7])=[O:6].Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH2:14]([O:13][C:11]([O:2][N:3]=[C:4]([C:8]#[N:9])[C:5]([NH2:7])=[O:6])=[O:12])[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of water (100 ml) and acetone (15 ml), sodium salt of 2-hydroxyimino-2-cyanoacetic acid amide (19.6 g) is added, and the obtained solution in which a part of the sodium salt is present in a suspended state is cooled at 0°C. Ethyl chloroformate (15 g) is dropwise added thereto, and the resulting mixture is, after adjusted to pH 7 to 8 with the addition of an aqueous solution of sodium hydrogencarbonate, stirred at room temperature for 1 hour and then filtered to collect the precipitated crystals. To the filtrate, a small amount of acetonitrile is added, and the mixture is extracted with ether. The ether layer is washed with water, dried and concentrated to give crystals, which are put together with the above obtained crystals to obtain 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (22.5 g). A part of the product is recrystallized from ethyl acetate to give crystals melting at 194° to 196°C.

Aufarbeitung

additionis added
filtrationfiltered
customto collect the precipitated crystals
additionTo the filtrate, a small amount of acetonitrile is added
extractionthe mixture is extracted with ether
washThe ether layer is washed with water
customdried
concentrationconcentrated
customto give crystals, which
customabove obtained crystals

Quellen und Nachweise

ORD-Eintrag: ord-4f713c75f9c94f4fabe9e975c9ba1d94
Quelldatensatz: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US03976635

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