Synthesis of new ethyl 2-({2-[phenyl(pyridin-2-Yl)methylidene]hydrazinecarbothioyl}amino)-benzoate
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2024-03-17 16:21
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544.142.3:547-304.6 (14)
Chemical structure of matter (98)
Organic chemistry (484)
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RUSNAC, Anna, SHOVA, Sergiu, GULYA, Aurelian. Synthesis of new ethyl 2-({2-[phenyl(pyridin-2-Yl)methylidene]hydrazinecarbothioyl}amino)-benzoate. In: Natural sciences in the dialogue of generations, 14-15 septembrie 2023, Chişinău. Chişinău: Centrul Editorial-Poligrafic al USM, 2023, p. 220. ISBN 978-9975-3430-9-1.
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Natural sciences in the dialogue of generations 2023
Conferința "Natural sciences in the dialogue of generations"
Chişinău, Moldova, 14-15 septembrie 2023

Synthesis of new ethyl 2-({2-[phenyl(pyridin-2-Yl)methylidene]hydrazinecarbothioyl}amino)-benzoate

CZU: 544.142.3:547-304.6

Pag. 220-220

Rusnac Anna1, Shova Sergiu12, Gulya Aurelian1
 
1 Moldova State University,
2 “Petru Poni” Institute of Macromolecular Chemistry
 
Proiecte:
 
Disponibil în IBN: 19 octombrie 2023


Rezumat

Microorganisms have the possibility to develop resistance to different drugs and therefore the synthesis of new drugs with antimicrobial properties is necessary. In this paper, the synthesis of a new organic compound from the class of thiosemicarbazones is presented. Synthesis of new ethyl 2-({2-[phenyl(pyridin-2-yl)methylidene]hydrazinecarbothioyl}amino)benzoate (3), and determination of structure. Compound (3) was obtained through the two step (fig. 1): ethyl 2-aminobenzoate (1) was reacted with thiophosgene in the presence of sodium hydrogencarbonate, obtaining the ethyl 2isothiocyanatobenzoate (2) with 80% yield, which was then subjected to an addition reaction with 2-[hydrazinylidene(phenyl)methyl]pyridine with the formation of compound (3) with 90% yield. The reactions were monitoring by using thin layer chromatography.Figure 1. Synthesis of compound (3). The structure of compound (3) was confirmed by elemental analysis, 1H-NMR, 13C-NMR, FT-IR spectroscopy. Upon recrystallization from alcoholic solution of compound 3, single crystals were obtained, which were investigated by single-crystal X-ray diffraction (fig. 2).Figure 2. Crystalline structure and packing of compound (3) In the 1H, 13C NMR spectra, two tautomeric forms are present: 95% thione, 5% thiol. In the solid state, it crystallizes in the monoclinic system (common from the pharmaceutical point of view) with the C=S bond length of 1.667 Å, according to the study of the specialized literature, the interatomic distance corresponding to the double bond.

Cuvinte-cheie
synthesis, thiosemicarbazone, molecular structure