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Synthesis of disodium [ benzene ‐U‐ 14 C]‐(4‐chlorophenylthio)methylenediphosphonate, [ benzene ‐U‐ 14 C]‐tiludronate
Author(s) -
Burgos Alain,
Ellames George J.
Publication year - 1995
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.2580361107
Subject(s) - benzene , chemistry , yield (engineering) , medicinal chemistry , thiocyanate , acetanilide , benzene derivatives , salt (chemistry) , nuclear chemistry , organic chemistry , chemical synthesis , biochemistry , materials science , metallurgy , in vitro
Disodium [ benzene ‐U‐ 14 C]‐(4‐chlorophenylthio)methylenediphosphonate, [ benzene ‐ 14 C]‐Tiludronate, 2 , has been prepared in six steps from [ benzene ‐U‐ 14 C]‐acetanilide in an overall radiochemical yield of 41%. A key step in this transformation was the efficient conversion of [U‐ 14 C]‐4‐chloroaniline to [ benzene ‐U‐ 14 C]‐4‐chlorophenylthiocyanate, 5 , in 83% yield by treatment of the corresponding diazonium salt, 9 , with iron (III) thiocyanate. It should be noted that formation of the isomeric [ benzene ‐U‐ 14 C]‐4‐chlorophenylisothiocyanate, 11 , as a byproduct, was observed in only ∼ 1% yield.