Hemijska industrija 2010 Volume 64, Issue 5, Pages: 401-409
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New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid
Milisavljević Smiljka S., Marinković Aleksandar D., Milosavljević Milutin M.
A synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates by oxidation of ammonium salt of ethyl and isopropylxanthogenic acid in a presence of sodium hypochlorite and hydrogen peroxide were performed. Ammonium salt of ethyl and isopropylxanthogenic acid was obtained by the reaction of alkylammonium sulfate and sodium ethyl and isopropyl xanthate. Studies on a dependence of N-ethyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters (reaction time, molar ratio of oxidant and ethylamonium salt of isopropylxanthogenic acid) were performed. Optimal reaction conditions for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates were established. Synthesized compounds have been fully characterized by FTIR, 1H NMR and MS data, while purity has been determined by GC method. A plausible pathway for the N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates synthesis, in the presence of the oxidative agents sodium hypochlorite and hydrogen peroxide, was proposed. The presented synthetic methods has been developed at laboratory and applied at semi-industrial level. The developed optimal method provides a powerful and versatile method for the preparation of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates. This new optimized method offer several benefits, namely, simple operation, mild reaction conditions, bypass of hazardous organic solvents, moderately toxic and inexpensive reagents, and also short reaction times and high product yields.
Keywords: N-alkyl-O-isopropyl thiocarbamate, N-alkyl-O-ethyl thiocarbamate, hydrogen peroxide, sodium hypochlorite, synthesis
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