Premium
Identification of an intact sydnonimine ring depending on the reaction substituents of mesocarb by gas chromatography/mass spectrometry
Author(s) -
Lee JeongAe,
Jeung Hyeonsook,
Kim Keon,
Lho Dongseok
Publication year - 1999
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199910)34:10<1079::aid-jms869>3.0.co;2-m
Subject(s) - chemistry , methyl iodide , ketene , ring (chemistry) , mass spectrometry , gas chromatography , medicinal chemistry , nucleophile , pyrolysis , organic chemistry , chromatography , catalysis
Trifluoroacylated, trimethylsilylated and methylated mesocarb (3‐(1‐methyl‐2‐phenylethyl)‐5‐[[(phenylamino) carbonyl]amino]‐1,2,3‐oxadiazolium) were analyzed by gas chromatography/mass spectrometry (GC/MS). In trifluoroacylation, N ‐trifluoroacylated sydnophen (SP‐NTFA), where the exocyclic nitrogen atom of the sydnonimine ring attacks N ‐methylbis(trifluoroacetamide), was identified by GC/MS. However, in trimethylsilylation, C ‐trimethylsilylated sydnophen (SP‐CTMS), where the C‐4 atom of the sydnonimine ring attacks N ‐methyl‐ N ‐trimethylsilyltrifluoroacetamide, was detected. SP‐NTFA and SP‐CTMS are intermediates of mesocarb in pyrolysis, and retain an intact sydnonimine ring. In methylation, a ketene form of mesocarb reacts as a nucleophile with methyl iodide to produce methylated N ‐nitroso‐ N ‐cyanomethylamphetamine. Thus, depending on the reaction substituents, the intermediate of mesocarb in pyrolysis was identified to be either an intact sydnonimine ring skeleton or an open‐ring compound using GC/MS. Copyright © 1999 John Wiley & Sons, Ltd.