| Phosphorothioates are very important organic intermediates, and are well-knownas pesticides in agriculture. In this paper, we introduced a new method to synthesizephosphorothioates, and a series of phosphorothioates were prepared.Phosphorothioates were yielded from the reactions of phosphite andTCT-activated DMSO in refluxing acetonitrile. The optimized reaction condition isthat the molar ratio of phosphite, cyanuric chloride, and DMSO is1:0.8:5in refluxingacetonitrile,To further study the scope of this new reaction, we explored the reactions usingDMSO-d6, dibutylsulfoxide and cyclic sulfoxide. Dimethyl phosphite was used as abenchmark in this paper and we got71%yield using DMSO,69%yield usingDMSO-d6,56%yield using dibutylsulfoxide. But we did not get the target productusing cyclic sulfoxide.Through this method, we obtained14phosphorothioates, of which9phosphorothioates are new compounds. All of the products were analyzed by IRand1H-NMR, and all new compounds were further analyzed by13C-NMR,31P-NMRand HRMS.This method is operationally simple and the reaction conditions are mild. Indeed,it gave the phosphorothioates in moderate yields and the labelling purity of theproducts is excellent. |
