Reassessment of the methyl derivatization reaction of carbamates with sodium hydride/dimethyl sulfoxide/methyl iodide for their determination by gas chromatography

A deep revision of the carbamate methyl derivatization reaction with sodium hydride/dimethyl sulfoxide/methyl iodide was carried out. Representative carbamates, R 1–NH–COO–R 2, mainly N-methyl and N-aryl ones, have been studied in order to clarify which carbamates undergo this reaction. Two possible...

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Bibliographic Details
Published in:Journal of Chromatography A 2006-11, Vol.1132 (1), p.241-247
Main Authors: Crespo-Corral, E., Santos-Delgado, M.J., Mª Polo-Díez, L., Sanz-Perucha, J.
Format: Article
Language:English
Subjects:
Alkyl derivatization reaction
Analytical chemistry
Carbamates
Carbamates - analysis
Carbamates - chemistry
Chemistry
Chromatographic methods and physical methods associated with chromatography
Chromatography, Gas - methods
Dimethyl Sulfoxide - chemistry
Exact sciences and technology
Gas chromatographic methods
Gas chromatography (GC)
Hydrocarbons, Iodinated - chemistry
Molecular Structure
Reproducibility of Results
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Summary:A deep revision of the carbamate methyl derivatization reaction with sodium hydride/dimethyl sulfoxide/methyl iodide was carried out. Representative carbamates, R 1–NH–COO–R 2, mainly N-methyl and N-aryl ones, have been studied in order to clarify which carbamates undergo this reaction. Two possible reaction routes are proposed; the route depends on the carbamate substituent (–OR 2 group) more than on the methyl or aryl groups joined to the NH moiety as literature indicates. The classification of carbamates in N-methyl and N-aryl is not suitable to predict the methylation pathway. A laboratory-made closed reactor allows handling the reagents involved, minimizing hazards and simplifying the procedure for rapid analysis.
ISSN:0021-9673
DOI:10.1016/j.chroma.2006.07.056