Methanol → 7-[{5-(2-Hydroxy-ethyl)-1,2,4-oxadiazol-3-yl}-methyl]-theophylline

HRID 1285169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285169
[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].[CH3:19][CH2:20][O-:21].[Na+].[CH3:23]O>>[OH:21][CH2:20][CH2:19][C:23]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

Komponenten

4

Edukt 3

HCID 887MethanolHCID 2723922Sodium ethoxideHCID 30574902-(Theophyllin-7-yl)-acetamidoxime

Produkt 1

HCID 202499747-[{5-(2-Hydroxy-ethyl)-1,2,4-oxadiazol-3-yl}-methyl]-theophyllineAusbeute 87 %

Versuchsvorschrift

5.04 g. of 2-(theophyllin-7-yl)-acetamidoxime, 4.8 g. hydracrylyc acid ethyl ester, 2.16 g. of sodium ethylate and 100 cm3 of methanol are heated under pressure at 100° C. for 12 hours. The solvent is distilled off and the residue is crystallized from water. 5.3 g. (87% yield) of 7-[{5-(2-hydroxy-ethyl)-1,2,4-oxadiazol-3-yl}-methyl]-theophylline are obtained, m.p.: 145° C. The raw hydroxy ethyl compound is heated with 20 cm3 thionyl chloride and 20 cm3 benzene for 2 hours. The solvent is distilled off and the obtained 7-[{5-(2-chloroethyl)-1,2,4-oxadiazol-3-yl}-methyl]-theophylline is stirred in 50 cm3 of dimethylformamide with 6 cm3 diethylamine and 5 g. of potassium carbonate vigorously for 10 hours at 100° C. 4.4 g. (61% yield) of 7-[{ 5-(2-diethylaminoethyl)-1,2,4-oxadiazol-3-yl}-methyl]-theophylline are obtained. M.p.: 65°-68° C. (cyclohexane).

Aufarbeitung

  1. distillationThe solvent is distilled off
  2. customthe residue is crystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-89bd60adf7d345b7a9c217e7076640aa
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04565817

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