Six 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one compounds and two 4-aryl-1- [2-(acetamido)-3-(4-chlorophenyl)acryloyl]thiosemicarbazide compounds were synthesized by reaction of aromatic aldehydes or reaction of aryl isothiocyanates, respectively with 2-(acetamido)-3-(4-chlorophenyl)acrylohydrazide which was prepared starting from 4-chlorobenzaldehyde and acetylglycine via 4-(4-chlorobenzylidene)-2-methyloxazol5(4H)-one. The structures of the synthesized compounds were determined by IR, NMR and mass spectral data. | Vietnam Journal of Chemistry, International Edition, 54(4): 496-500, 2016 DOI: Transformation of 2-(acetamido)-3-(4-chlorophenyl)acrylohydrazide into 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)ones and 4-aryl-1-[2-(acetamido)-3-(4-chlorophenyl) acryloyl]thiosemicarbazides Nguyen Tien Cong*, Truong Ngoc Anh Luan Department of Chemistry, Ho Chi Minh City University of Education Received 2 June 2016; Accepted for publication 12 August 2016 Abstract Six 1-arylideneamino-4-(4-chlorobenzylidene)-2-methyl-1H-imidazolin-5(4H)-one compounds and two 4-aryl-1[2-(acetamido)-3-(4-chlorophenyl)acryloyl]thiosemicarbazide compounds were synthesized by reaction of aromatic aldehydes or reaction of aryl isothiocyanates, respectively with 2-(acetamido)-3-(4-chlorophenyl)acrylohydrazide which was prepared starting from 4-chlorobenzaldehyde and acetylglycine via 4-(4-chlorobenzylidene)-2-methyloxazol5(4H)-one. The structures of the synthesized compounds were determined by IR, NMR and mass spectral data. Keywords. 2-(acetamido)-3-(4-chlorophenyl)acrylohydrazide, imidazolin-5(4H)-one, thiosemicarbazide. 1. INTRODUCTION 2-(Acetamido)-3-(4-chlorophenyl)acrylo hydrazide (1) was synthesized and then, transformed into some N-substituted hydrazide [1,2]. Some new compounds were synthesized and an unusual transformation was found out in the further research of transformations of the hydrazide (1). 2. EXPERIMENTAL General procedures: All chemicals and solvents were obtained from commercial sources and used without any further purification. Melting points were determined in open capillaries and the values are uncorrected. IR spectra were recorded in KBr discs on a Shimadzu FTIR 8400S spectrophotometer. NMR spectra were recorded on a Bruker Avance spectrometer (500 MHz for 1H-NMR and 125 MHz for 13C-NMR) using DMSO-d6 as solvent and tetramethylsilane ( ppm) as an internal standard. MS spectra were recorded on a Bruker micrOTOF-Q 10187 .
