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Synthesis of 14 C‐labelled compounds. I. Synthesis of 2 ( 14 C)‐dinitrosohexahydropyrimidine
Author(s) -
Brann Horst,
Bertram Barbara,
Wiessler Manfred
Publication year - 1977
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.2580130312
Subject(s) - chemistry , yield (engineering) , ether , aqueous solution , formaldehyde , condensation , benzene , silica gel , sodium nitrite , sodium , condensation reaction , medicinal chemistry , organic chemistry , nuclear chemistry , catalysis , materials science , physics , metallurgy , thermodynamics
Abstract A convenient procedure to synthesize 2– 14 C‐dinitroso‐hexahydropyrimidine (DNHP) is described. The synthesis begines with the condensation of 14 C‐formaldehyde and propylenediamine‐1,3 in benzene with azeotropic removal of water. The resulting bases are isolated from the reaction mixture as hydrochlorides and are nitrosated with sodium nitrite in aqueous medium at a constant pH of 4 to 5. After column chromatography on Silica gel and recrystallisation from ether 2– 14 C‐dinitroso‐hexahydropyrimidine (DNHP) is isolated in 30.7% yield based on 14 C‐fomaldehyde.