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Synthesis of singly 2H-, 3H-, and 14C- and doubly labeled acetaminophen, phenacetin, and p-acetanisidine

✍ Scribed by Kenneth K. Chan; K. Sandy Pang

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
396 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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