Synthesis, Spectral and Structural Study of N-[1-(N,N,N′,N′-Tetramethylphosphoramidoyl)- 1H-Benzimidazol-2-yl]-Propionimidic Ethyl Ether

Research paper by N. Raouafi, M. Freytag, P. G. Jones, K. Boujlel, M. L. BenKhoud

Indexed on: 01 Apr '05Published on: 01 Apr '05Published in: Structural Chemistry


The preparation of N-[1-(N,N,N′,N′-tetramethylphosphoramidoyl)-1H-benzimidazol-2-yl]-proponimidic ethyl ester 2 has been achieved by the reaction of N-(1H-benzimidazol-2-yl)-proponimidic acid ethyl ester 1 with N,N,N′,N′-tetramethylchlorophosphoramide. The structure of compound 2 has been determined by X-ray diffraction. The results of (1H, 13C, 31P) NMR, IR, EI-MS spectral data are consistent with those obtained from the X-ray diffraction. The compound crystallizes in the triclinic system, following the EsZ conformation. In the crystal, there are two weak C3–H3⋅s1 and C15–H15⋅sO1 intermolecular hydrogen bonds.