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N.C.A.[ 11 C]CO 2 as a safe substitute for phosgene in the carbonylation of primary amines
Author(s) -
Schirbel A.,
Holschbach M. H.,
Coenen H. H.
Publication year - 1999
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/(sici)1099-1344(199906)42:6<537::aid-jlcr215>3.0.co;2-3
Subject(s) - chemistry , phosgene , carbonylation , yield (engineering) , aniline , carbamate , triphosgene , organic chemistry , labelling , carbon monoxide , combinatorial chemistry , catalysis , materials science , metallurgy , biochemistry
An efficient one‐pot synthesis of [ 11 C]ureas and [ 11 C]isocyanates via dehydration of intermediately formed carbamate salts is described as a general alternative to their formation via [ 11 C]phosgene. After optimization of the reaction parameters, in‐target produced n.c.a. [ 11 C]CO 2 can be used for labelling in a one pot reaction within a very short reaction time of 10 minutes resulting in good radiochemical yields. The developed method has been applied to the 11 C‐carbonylation of aniline, benzyl‐ and phenethylamine and 1,2‐diaminobenzene yielding the appropriate n.c.a. [ 11 C]ureas in about 65, 85, 25 and 70% radiochemical yield (RCY), respectively. The presented reaction sequence can be handled easily and safely and lends itself to simple automation. Copyright © 1999 John Wiley & Sons, Ltd.