The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of some derivatives of 2-nitroimidazole with potential anti-Trichomonas activity》. Authors are Lancini, G. C.; Maggi, N.; Sensi, P..The article about the compound:5-Chloro-1-methyl-4-nitroimidazolecas:4897-25-0,SMILESS:C1=NC(=C(Cl)[N]1C)[N+]([O-])=O).HPLC of Formula: 4897-25-0. Through the article, more information about this compound (cas:4897-25-0) is conveyed.
2-Nitroimidazole (I) (azomycin), an antibiotic isolated from a Streptomyces strain, was submitted to various substitutions, and the reaction products tested for antiTrichomonas activity. In order to prepare I a Streptomyces was cultivated at 28° for 96 hrs., the pH of the culture adjusted to 8, the mycelium filtered off, and the filtrate acidified to pH. Extraction of a 10-l. portion with AcOEt, followed by evaporation of the solvent yielded 0.7 g. I, m. 284° (decomposition)(MeOH). (Nakamura, CA 50, 15897g). I (1.13 g.) was added at 0° to a mixture of 15 ml. 86% HNO3 and 5 ml. Ac2O, the solution heated 2 hrs. at 100° and 30 min. at 115° (bath temperature), and the product, which precipitated upon addition of 150 ml. ice-H2O, extracted with AcOEt, to yield 0.72 g. 2,4(5)-dinitroimidazole (II), 266-8° (MeOH). I (1.13 g.) in 200 ml. AcOH was mixed with 10 ml. 20% Br in AcOH, the mixture refluxed until the color disappeared, concentrated in vacuo, and the residue treated with H2O to give 0.9 g. 2,4,5-tribromoimidazole (III), m. 219-21° (MeOH or CHCl3). suspension of 1 g. II in 10 ml. ethylene chlorohydrin was refluxed 15 hrs., the solvent evaporated, and the residue treated with 5 ml. CHCl3 to yield 0.7 g. 4(5)-nitro-5(4)-chloroimidazole (IV), m. 214-16°. IV (0.2 g.) was suspended in 30 ml. 1% ethereal CH2N2 and the mixture kept at room temperature 12 hrs., and concentrated to yield 0.06 g. 1-methyl-4-nitro5-chloroimidazole (V), m. 146-8° (EtOH). From the mother liquor, 0.10 g. isomeric 1-methyl-4-chloro-5-nitroimidazole (VI), m. 76-8° (C6H6-petr. ether), was isolated. To 1.36 g. I in 100 ml. absolute EtOH were added 1.2 g. pyrrolidine-HCl and 1.25 ml. 38% aqueous HCHO, the mixture refluxed 12 hrs., cooled to 50°, filtered, and the filtrate concentrated to yield 1.12 g. 2-nitro-4(5)-pyrrolidinomethylimidazole (VII), m. 212-15° (EtOH). Similar treatment of 1.36 g. I with 1.4 g. morpholine-HCl gave 1.25 g. 2-nitro-4(5)-morpholinomethyliminazole (VIII), m. 156-8° (EtOH). The ultraviolet spectra of VII and VIII were given. Attempts to sulfonate or tosylate I only yielded starting material. All of the new compounds discussed were active against T. vaginalis.
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Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts