N-BENZYLOXY-N-METHOXYREA. SYNTHESIS AND STRUCTURE
DOI:
https://doi.org/10.15421/jchemtech.v32i1.292868Keywords:
N-acyloxy-N-alkoxyureas; N-alkoxy-N’-сhloroureas; N,N-dialkoxyureas; N-benzyloxy-N’-methoxyurea; synthesis; structure.Abstract
Aim. To synthesize of N-benzyloxy-N-methoxyurea from the methanolysis of N-acetoxy-N-benzyloxyurea and to investigate its structure using the XRD study. Methods. Mass spectrometry, 1H and 13C NMR spectroscopy, IR spectroscopy, XRD study. Results. N-Benzyloxy-N-chlorourea was synthesized with high yield of the N-benzyloxyurea by the chlorination by tert-butyl hypochlorite. We have proved that the interaction of with sodium acetate in acetonitrile medium at room temperature leads to the formation of N-acetoxy-N-benzyloxyurea with the moderate yield. It has been also found that the methanolysis of N-acetoxy-N-benzyloxyurea at room temperature is a convenient method of the N-benzyloxy-N-methoxyurea synthesis. The structure of the synthesized N-benzyloxy-N-chlorourea, N-acetoxy-N-benzyloxyurea and N-benzyloxy-N-methoxyurea was confirmed by the data of 1H and 13C NMR spectra, IR spectra and mass spectra. Also, the XRD study of N-benzyloxy-N-methoxyurea structure proved our assumptions: O–N–O nitrogen atom (N2) in N-benzyloxy-N-methoxyurea is sp3 hybridized and has pyramidal configuration. The carbamoyl nitrogen atom (N1) has planar configuration. After comparison of the amide bond of the received N-benzyloxy-N-metoxyurea with the similar bond in unsubstituted N-benzyloxyurea and H2N(1)–C(=O) bond of N-benzyloxy-N-methoxyurea we have found the significant elongation of the amide BnO(MeO)N(2)–C(=O) bond of N-benzyloxy-N-methoxyurea. The molecular packings in the crystal of N-benzyloxy-N-methoxyurea and N-benzyloxyurea is different. Conclusions. As the result of our study the anomeric N-benzyloxy-N-chlorourea, N-acetoxy-N-benzyloxyurea and N-benzyloxy-N-methoxyurea have been synthesized. The structure of N-benzyloxy-N-methoxyurea has been thoroughly analyzed.
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