Geminal systems. 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas,carbamates, and benzamides |
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| Authors: | Shtamburg V G Klots E A Pleshkova A P Avramenko V I Ivonin S P Tsygankov A V Kostyanovsky R G |
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| Institution: | (1) Dnepropetrovsk National University, 134 ul. Nauchnaya, 49050 Dnepropetrovsk, Ukraine;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(3) N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991 Moscow, Russian Federation |
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| Abstract: | Procedures were developed for the synthesis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides by the reactions of the corresponding N-alkoxy-N-chloro derivatives with sodium carboxylates in MeCN. N-Chloro-N-ethoxy-p-toluenesulfonamide was inert in this reaction. Alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and tert-alkylamines afforded the corresponding N,N-dialkoxy derivatives, whereas alcoholysis of N-acetoxy-N-ethoxybenzamide gave rise to alkyl benzoates. |
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| Keywords: | N-alkoxy-N-chloro derivatives of ureas carbamates benzamide and p-toluenesulfonamide sodium carboxylates N-acyloxy-N-alkoxy derivatives of ureas carbamates and tertiary alkylamines alcoholysis 1H NMR spectra mass spectra N N-dialkoxyamino derivatives of ureas and carbamates |
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