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Synthese d'un diuretique marque au carbone 14: Acide dichloro‐2,3 [thenoyl‐2 ( 14 C = 0)]‐4 phenoxy acetique (D.C.I. acide tiénilique)
Author(s) -
Herbert M.,
Pichat L.
Publication year - 1976
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.2580120313
Subject(s) - chemistry , medicinal chemistry , yield (engineering) , sodium , methanol , decomposition , nuclear chemistry , oxalyl chloride , benzene , derivative (finance) , phenol , organic chemistry , materials science , metallurgy , economics , financial economics
2‐Thenoic acid ( 14 C = 0) 1 is prepared in 75 % radioactive yield by carbonation with 14 CO 2 of 2‐thienyL‐magnesium bromide. Boiling of 1 with oxalyl chloride gives rise to 2‐thenoylchloride ( 14 CO) which is not isolated and is condensed with 2,3 dichLoroanisoLe under FrieLdeL‐Grafts conditions. Ketone 3 is demeth Lated with AlCl 3 in benzene to give rise to 4‐ 2‐thenoyl ( 14 C = O)‐2,3‐dichloro phenol 4. The sodium derivative of 4 is condensed in D.M.F. with sodium chloracetate to Lead to the title compound with an overall yield of 16 % based on 14 CO 2 – TieniLic acid‐ 14 c, specific activity: 50 mCi/mMole, has been found to be sensitive to self‐irra‐diation decomposition in the dry state at ‐ 25%° C. Radiation decomposition is minimized at 24 mCi/mMole in methanol solution.