Ethyl Acrylate → 7-[[5-(2-Ethoxy-ethyl)-1,2,4-oxadiazol-3-yl]-methyl]-theophylline

HRID 1285168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285168
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15](=[N:17][OH:18])[NH2:16])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[C:19]([O:23][CH2:24][CH3:25])(=O)[CH:20]=[CH2:21].CC[O-].[Na+]>C(O)C>[CH2:24]([O:23][CH2:19][CH2:20][C:21]1[O:18][N:17]=[C:15]([CH2:14][N:10]2[C:11]3[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=3[N:8]=[CH:9]2)[N:16]=1)[CH3:25]

Komponenten

5

Edukt 3

HCID 8821Ethyl AcrylateHCID 2723922Sodium ethoxideHCID 30574902-(Theophyllin-7-yl)-acetamidoxime

Produkt 1

HCID 202499377-[[5-(2-Ethoxy-ethyl)-1,2,4-oxadiazol-3-yl]-methyl]-theophyllineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

12.6 g. 2-(theophyllin-7-yl)-acetamidoxime, 10 g. of ethyl acrylate, 220 cm3 of ethanol and 3.4 g. of sodium ethylate are heated under stirring for 15 hours. 16 g. (95% yield) of raw 7-[[5-(2-ethoxy-ethyl)-1,2,4-oxadiazol-3-yl]-methyl]-theophylline are obtained. This product is heated with 20 cm3 diethylamine under stirring for 8 hours on a 110° C. oil bath. The mixture is then evaporated at reduced pressure, washed by trituration with water and salt is formed with 5.8 g. of maleic acid in hot ethanol. 16.2 g. (68% yield) of 7-[{5-(2-diethylamino-ethan-1-yl)-1,2,4-oxadiazol-3-yl}-methyl]-theophilline-maleinate are are obtained. M.p.: 125°-128° C.

Quellen und Nachweise

ORD-Eintrag
ord-5dd7d897c6de412d8202acab2f9d3303
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04565817

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