Study of Reactions of 2,2-Dichloro-N-(Substituted Phenyl) Acetamide With 1H-Benzo[d]1,2,3-Triazole
Keywords:
Substituted aniline, Dichloroacetyl chloride, 1H – benzo [d] 1,2,3 - triazole, SynthesisAbstract
Synthesis of 2,2-dichloro-N-(substituted phenyl) acetamid (a1-4) via treated substituted aniline with dichloroacetyl chloride in the present of anhydrous K2CO3 in CH2Cl2. The later 1H-benzo[d]1,2,3-triazole (2) were reacted with 2,2-dichloro-N-(4-chloro phenyl) acetamid (a1), 2,2-dichloro-N-(3-nitro phenyl) acetamid (a2), 2,2-dichloro-N-(4-methoxy-3-nitrophenyl) acetamid (a3), 2,2-dichloro-N-(p-tolyl) acetamid (a4) in the present of anhydrous K2CO3 in acetone under reflux to give 2-(1H-benzo[d]1,2,3-triazol-1-yl)-2-chloro-N-(4-chloro phenyl) acetamide (3), 2-(1H-benzo[d]1,2,3-triazol-1-yl)-2-chloro-N-(3-nitro phenyl) acetamide (4), 2-(1H-benzo[d]1,2,3-triazol-1-yl)-2-chloro-N-(4-methoxy-3-nitro phenyl) acetamide (5) and 2-(1H-benzo[d]1,2,3-triazol-1-yl)-2-chloro-N-(p-tolyl) acetamide (6) respectively.
All the synthesized compounds were characterized on the basis of melting point, TLC, IR, 1HNMR, 13CNMR and mass spectrometry.
References
Al-Omran, F., Mohareb, R. M., Abou El-Khair, A., (2002), synthesis and biological effects of new derivatives of benzotriazole as antimicrobial and antifungal agents, J. heterocyclic chem, 39, 877 – 883.
Alpana, A., Shrikant, M., Pratyush, K., Abhibnav, B., Ruchita, T., (2020), Review on synthetic study of benzotriazole, GSC biological and pharmaceutical sciences, 11 (02), 215 - 225. https://doi.org/10.30574/gscbps.2020.11.2.0137
Bashir, H., Hashim, G. and Abdalfarg, N., (2021), Synthesis of Benzotriazole Derivatives, international Invention of Scientific Journal, 05 (3), 17 - 26. https://doi: 10.1016/j.ejmech.2012.05.028
Jain, N. P., Upassani, C. D., Kalkotwar, R. S., Jain, U. P., (2013), Synthesis and anti – inflammatory activity of N – (alkyl or aryl) – 2 – (1H – benzotriazole -1 – yl) acetamide derivatives, Research journal of pharmaceutical, biological and chemical sciences, 4(3) 1470 -1480.
Jamkhandi, C. M., Disouza, J. I., (2013), Synthesis and antimicrobial evaluation of 1H – Benzotriazol -1 -yl {2- hydroxy -5-[(E) phenyldiazenyl] phenyl} methanone derivative, international journal of pharmacy and pharmaceutical sciences, 5(3)225 -228.
Noolvi, M. N., Patel, H. M., Kaur, M., (2012), Benzotriazoles: search for anticancer aggents, European journal of medicinal chemistry, 54, 447-462.
Ram, V. J., Sethi, A., Nath, M., Pratap, R., (2019), Five-membered heterocycles. In The Chemistry of Heterocycles, 149 - 478. Elsevier. https://doi.org/10.1016/B978-0-08-1010334.00005-X.
Suma, B.V., Natesh, N. N., Madhavan, V., (2011), Benzotriazole in medicinal chemistry: An overview, Journal of chemical and pharmaceutical research, 3(6):375-381.
Ueno, L. T., Ribeiro, R. O., Rocha, M.S., Suárez-Iha, M. E.V., Iha, K., Machado, F. B. C., (2003), About the benzotriazole tautomerism: An ab initio study, Journal of Molecular Structure (theochem),207-215. https://doi.org/10.1016/j.theochem.2003.09.004
Uesaka, T., Ishitani, T., Sawada, R., Maeda, T., Yagi, S., (2020), Fluorescent 2 – phenyl - 2H - benzotriazole dyes with intramolecular N–H⋅⋅⋅N hydrogen bonding: Synthesis and modulation of fluorescence properties by proton - donating substituents, Dyes and pigments, https://doi.org/10.1016/j.dyepig.2020.108672
