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Synthesis of singly 2 H‐, 3 H‐, and 14 C‐ and doubly labeled acetaminophen, phenacetin, and p‐acetanisidine
Author(s) -
Chan Kenneth K.,
Pang K. Sandy
Publication year - 1982
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.2580190303
Subject(s) - chemistry , phenacetin , yield (engineering) , acetic anhydride , acylation , tritium , medicinal chemistry , hydrolysis , deuterium , alkylation , acetic acid , alkoxy group , alkyl , acetaminophen , radiochemistry , nuclear chemistry , organic chemistry , catalysis , chromatography , biochemistry , materials science , physics , nuclear physics , metallurgy , quantum mechanics
Several efficient procedures for the synthesis of deuterium, tritium, and 14 C–labeled acetaminophen, phenacetin, and p‐acetanisidine are described. p‐Aminophenol was acylated by the appropriate acetic anhydride under mild conditions yielding labeled acetaminophen. With 0‐alkylation using NaCH 2 SOCH 3 and appropriate labeled and unlabeled alkyl halides, labeled phenacetin and p‐acetanisidine were also obtained. Phenacetin labeled both with 14 C on the acyl group and deuterium on the ethoxy group was synthesized in high yield by acylation of p‐phenetidine‐d 5 . The last compound was obtained by acid hydrolysis of phenacetin‐d 5 synthesized previously.