СИНТЕЗ ХЛОРИДІВ N-АЛКОКСИ-N-(ТРИФЕНІЛФОСФОНІЙ)СЕЧОВИН ТА ХЛОРИДІВ N-АЛКОКСИ-N-(ДИМЕТИЛСУЛЬФОНІЙ)СЕЧОВИН. ЇХ ПЕРЕТВОРЕННЯ У 3-АЛКОКСИ-5-ФЕНІЛІМІДАЗОЛІДИН-2,4-ДІОНИ

Aim. The article reports the synthesis of previously unknown N-alkoxy-N-(triphenylphosphonium)urea chlorides and N-alkoxy-N-(dimethylsulfonium)urea chlorides from N-chloro-N-alkoxyureas, and investigates their interactions with anhydrous phenylglyoxal. Methods. 1H, 13C and 31P NMR spectroscopy, mass spectrometry, a single crystal X-ray diffraction study. Results. It has been shown that the interaction of N-chloro-N-alkoxyureas with triphenylphosphine in anhydrous ether at room temperature yields unstable unknown N-alkoxy-N-(triphenylphoshonium)urea chlorides. Their structures were determined based on analysis of 1H, 31P and 13C NMR spectra. This reaction is a new method of N–P bond formation. It was also found that N-alkoxy-N-(triphenylphosphomium)urea chlorides react with anhydrous phenylglyoxal yielding 3-alkoxy-5-phenylimidazolidine-2,4-diones and triphenylphosphine oxide. The structure of 3-methoxy-5-phenylhydantoin was studied by X-ray diffraction study. It was found that N-chloro-N-alkoxyureas react with dimethyl sulfide in anhydrous ether yielding unstable N-alkoxy-N-(dimethylsulfonium)urea chlorides. The N-methoxy-N-(dimethylsulfonium)urea chloride interaction with freshly distilled phenylglyoxal gives 3-methoxy-5-phenylimidazolidine-2,4-dione and dimethyl sulfoxide. Conclusions. N-Alkoxy-N-(triphenylphoshonium)urea chlorides and N-alkoxy-N-(dimethylsulfonium)urea chlorides were synthesized for the first time. It was shown that N-alkoxy-N-(triphenylphoshonium)urea chlorides and N-alkoxy-N-(dimethylsulfonium)urea chlorides can be used as starting materials to obtain the 3-alkoxy-5-phenylimidazolidine-2,4-diones.