Study of the Kinetics of the Nucleophilic Substitution Reaction of 7-amino-3-tert-butyl-4-oxo-8-cyano-6h-pyrazolo[5,1-c][1,2,4]-triazine with Benzyl Chloride

The purpose of the study.The aim of the work was to study the kinetics of the nucleophilic substitution reaction between 7-amino-3-tert-butyl-4-oxo-8-cyano-6H-pyrazolo[5,1-c][1,2,4]-triazine and benzyl chloride.

Research methods.7-amino-1-benzyl-3-tert-butyl-4-oxo-8-cyano-6H-pyrazolo[5,1-c][1,2,4]-triazine was synthesized by the nucleophilic substitution reaction by the interaction of 7-amino-3-tert-butyl-4-oxo-8-cyano-6h-pyrazolo[5,1c][1,2,4]-triazine with benzyl chloride.

The IR spectra of the initial and obtained compounds were obtained using the Agilent Cary 660 FTIR IR-Fourier spectrometer. UV spectra were taken on a Shimadzu UV-1800 spectrophotometer and a digital STUART Melting point SMP30 device with a resolution of 0.10С was used to determine the melting temperature.

Kinetic control of the process under study was carried out by TLC (planar chromatography). During the analysis, Sorbfil PTSH-AF-V-UV chromatographic plates with high efficiency were used. The chromatograms were developed at a wavelength of 254 nm using a SORBFIL video sensor based on a lighting camera. Chromatograms were processed in the computer program "Sorbflil TLC View 1.8".

Results.The interaction of 7-amino-3-tert-butyl-4-oxo-8-cyano-6H-pyrazolo[5,1-c][1,2,4]-triazine and benzyl chloride PhCH2Cl produced a white crystalline substance with T_pl =194,6-195,2⁰C. The yield of the product was 1,1g (79% of the theoretical). When analyzing the IR spectrum of the obtained compound, the presence in its structure was revealed: 1,2,4-triazine ring (at 943 and 1096 cm^-1 peaks characteristic of the "skeletal vibrations" of the triazine ring were detected); pyrazole ring (peaks at 1591 and 1350 cm^-1), NH₂ groups (at 3202 cm^-1, a peak corresponding to the valence vibrations of the amino group was manifested), C≡N groups (peak at 2220 cm^-1), C=O groups (peak at 1702 cm^-1), groups with (4)=O (peak at 1626 cm^-1). The existence of peaks of the benzyl group is analyzed using the NIST database. Transitions were observed in the UV spectrum at 255nm (π→σ* transition of the functional group C=O) and 318 nm (π→π* transition of the aromatic system).

To determine the kinetic parameters of the reaction, the data obtained using the TLC method were processed using differential and integral methods, as well as the Van't-Hoff method. 

Conclusion. During kinetic studies, it was found that the nucleophilic substitution between 7-amino-3-tert-butyl-4-oxo8-cyano-6H-pyrazolo[5,1-c][1,2,4]-triazine and benzyl chloride has that the reaction order is 0,9, the rate constant is 0.0064 min^-1.

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