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Synthesis of the 5‐nitrofuran 2,4‐diacetylamino‐6‐(5‐nitro‐2‐furyl)‐1,3,5‐triazine‐6‐ 14 C
Author(s) -
Doose Dennis R.,
Hoener BettyAnn
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200407
Subject(s) - chemistry , acetic anhydride , yield (engineering) , nitro , nitrofuran , triazine , acetic acid , ether , organic chemistry , medicinal chemistry , condensation , nuclear chemistry , catalysis , materials science , alkyl , thermodynamics , physics , biology , metallurgy , genetics
The synthesis of the 5‐nitrofuran 2,4‐diacetylamino‐6‐(5‐nitro‐2‐furyl)‐1,3,5‐triazine‐6‐ 14 C is described. Furyllithium in ether is carboxylated with radio‐carbon dioxide generated from Ba 14 CO 3 . The furoic‐carbonyl‐ 14 C acid is then esterified with diazoethane and nitrated with nitronium acetate. The resulting ethyl 5‐nitro‐2‐furoate‐carbonyl‐ 14 C is then condensed with biguanide to give 2,4‐diamino‐6‐(5‐nitro‐2‐furyl)‐1,3,5‐triazine‐6‐ 14 C. The final product is then obtained by refluxing the condensation product in acetic anhydride to give a yield of 18% based on the amount of Ba 14 CO 3 at a specific activity of 43.2mCi/mmole.