On April 20, 1966, Fitzmaurice, Colin published a patent.Reference of 2-Nitro-1H-benzo[d]imidazole The title of the patent was Nitroimidazoles. And the patent contained the following:
Nitroimidazole derivatives (I) in which R = H or an alkyl group with 1-3 C atoms and X = an alkoxy or acyloxy group with 1-4 C atoms are prepared to be used in pharmaceutical preparations for the treatment of protozoal infections. Thus, 10 g. 4-nitroimidazole (II) and 12 ml. ClCH2OMe was heated 3 hrs. in a sealed tube at 100°, the cooled solution was taken up in H2O, made alk. with Na2CO3, and extracted with CHCl3 to give 6.3 g.I (R= H, X = OMe),m. 66.5-67° (C6H6). In the same way, 2.5 g. 2-methyl-4-nitroimidazole, and 5 ml. ClCH2OMe gave 1.4 g. I (R = Me, X = OMe), m. 71.5-2.5° (Et2O). II (1.7 g.) and 4 ml. ClCH2OAc was heated 1 hr. at 140°, the mixture was cooled overnight, treated with H2O and Na2CO3, and extracted with CHCl3. The residual oil of the evaporated (in vacuo) CHCl3 extract was triturated with Et2O and the precipitate recrystallized from EtOAc, giving 1.5 g. I (R = H, X = CH2OAc) (III), m. 83.5-4.5°. III, m. 88-8.5°, was also prepared in 6.2-g. yield by refluxing 5 g. II, 5 ml. AcOCH2Cl, and 3.5 g. K2CO3 4 hrs. in 50 ml. Me2CO, evaporating the filtered solution in vacuo, and extracting the residue with EtOAc, boiling the extract with C, and precipitating it with petroleum ether. II (6 g.) and 7.5 ml. EtCO2CH2Cl (IV) was refluxed 3 hrs. and cooled overnight, the excess IV was distilled in vacuo, and the residue treated in H2O with Na2CO3, extracted with CHCl3, giving I (R = H, X = EtCO2CH2), m. 61-2° (Et2O-petroleum ether). The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Reference of 2-Nitro-1H-benzo[d]imidazole
2-Nitro-1H-benzo[d]imidazole(cas:5709-67-1) belongs to imidazoles. It is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Reference of 2-Nitro-1H-benzo[d]imidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem