Thiophosphoramidates can be synthesized from the reaction of thiophosphoryl chlorides with primary amines. These products can later be used to create novel thiocarbonyl compounds. This reaction involves a nucleophilic attack by the amine on the phosphorus, thereby creating a new N—P bond and replacing the chloride leaving group. The mechanism of this reaction bears some similarity to esterification of acyl chlorides. The goal of this study was to evaluate the effect that changing the structure of the amine has on this substitution reaction. Thiophosphoramidates were synthesized by reacting dimethoxythiophosphoryl chloride with a variety of primary amines, including butylamine and benzylamine. Reactions were carried out in methylene chloride in basic conditions at 0°C under inert atmosphere, followed by extraction and work up. Products were identified and described using 1H-NMR, 31P-NMR, 13C -NMR and IR. Product yield and purity were assessed using these spectroscopies and compounds were characterized structurally. In future studies, these thiophosphoramidate products will be used as reactants to synthesize novel thiocarbonyl compounds, such as mixed imides and pseudotripeptides. By conducting this research, students gain invaluable experience using instrumentation at greater depth, providing preparation for future careers in chemistry and research, while contributing to the scientific knowledge base.

Synthesis and characterization of thiophosphoramidates

251st National Meeting (2016)

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