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

HRID 1285168Notes

Reaction equation

HRID 1285168 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-5dd7d897c6de412d8202acab2f9d3303
Source dataset
uspto-grants-1986_01
Patent number
US04565817

Reaction notes

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