Ethyl 3-cyano-3-phenylpyruvate → 2-(p-Methylthiophenyl)-5-phenyl-3,4-dioxoadiponitrile

HRID 267762

Reaktionsgleichung

Reaktionsgleichung von HRID 267762
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4](=[O:10])[C:5]([O:7]CC)=O)#[N:2].[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=1.[O-]CC.[Na+]>>[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:5](=[O:7])[C:4](=[O:10])[CH:3]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:1]#[N:2])[C:26]#[N:27])=[CH:21][CH:20]=1

Komponenten

4

Edukt 3

HCID 22845Ethyl 3-cyano-3-phenylpyruvateHCID 2723922Sodium ethoxideHCID 27600872-(4-(Methylthio)phenyl)acetonitrile

Produkt 1

HCID 215540552-(p-Methylthiophenyl)-5-phenyl-3,4-dioxoadiponitrile

Versuchsvorschrift

As described in Example 1, ethyl 3-cyano-3-phenylpyruvate is reacted with p-methylthiophenylacetonitrile in an alcoholic solution of sodium ethoxide to give 2-(p-methylthiophenyl)-5-phenyl-3,4-dioxoadiponitrile. The latter is refluxed in a mixture of water, glacial acetic acid and concentrated sulfuric acid to give a mixture of 4- and 4'-methylthiopulvinic acid which is then refluxed in acetic anhydride to result in the formation of 4-methylthiopulvinic acid lactone.

Quellen und Nachweise

ORD-Eintrag
ord-e6bc40fc25c746fba9810d2915f777aa
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03944571

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