Diethyl (ethoxymethylene)malonate → HCID 178507442, Verbindung

Reaktionsgleichung

[Na].Cl.Cl.[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[NH:10])=[CH:7][CH:6]=1.C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21]CC)=[O:20])C>C(O)C>[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[N:11]=[C:17]([OH:16])[C:18]([C:19]([OH:21])=[O:20])=[CH:24][N:10]=2)=[CH:7][CH:6]=1

Komponenten

Versuchsvorschrift

A solution of 14.8 g (0.642 mmol) of sodium in 750 ml of dry ethanol is stirred at 0° and 44.6 g (0.214 mmol) of 4-aminobenzamidine 2HCl [Shaw and Cooley, J. Am. Chem. Soc., 79, 3561 (1957)] is added. The mixture is stirred 5 minutes under nitrogen and 46.2 g (0.214 mmol) of diethyl ethoxymethylenemalonate is added. After stirring for 30 min, the mixture is refluxed for 4 hr and allowed to stand overnight at room temperature. The salt is filtered and washed with isopropanol. The salt is suspended in 214 ml of 2 N potassium hydroxide and stirred at 70° C. for 4 hr. After treating with a small amount of charcoal, the filtrate is added to 325 ml of 2 N HCl with stirring. The acid is filtered, washed with water, ethanol, and ether, and dried to give 50.8 g of the title compound, mp 312°-314° C. dec. The product is recrystallized from dimethylacetamide-water to give 44.5 g mp 313°-314° C. dec. ##EQU42##