Identification of an intact sydnonimine ring depending on the reaction substituents of mesocarb by gas chromatography/mass spectrometry

✍ Scribed by Lee, JeongAe; Jeung, Hyeonsook; Kim, Keon; Lho, Dong-seok

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 125 KB
• Volume: 34
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(199910)34:10<1079::aid-jms869>3.0.co;2-m

✦ Synopsis

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.