On May 18, 1966, there was a patent named 2-Nitroimidazoles.Computed Properties of 5709-67-1. And the patent contained the following:
Substituted 2-nitroimidazoles were prepared for use against protozoa, bacteria, and pathogenic fungi. 2-(p-Bromobenzeneazo)imidazole (50 g.) in EtOH hydrogenated over Raney Ni, and the red-brown oily product treated in 75 cc. H2O with 10 cc. concentrated H2SO4 and then 12 hrs. with 400 cc. absolute MeOH yielded crude 2-aminoimidazole sulfate (I), m. 255°, beginning to decompose at 278°, which recrystallized from boiling 3:1 H2O-EtOH gave I, m. 280° (decomposition). H2NCH2CH(OEt)2 (100 g.) and 162 cc. H2O treated 48 hrs. at room temperature with methylisourea sulfate and evaporated, and the viscous oily residue crystallized from 1100 cc. Me2CO yielded N-(2,2-diethoxyethyl)guanidine sulfate, m. 150-3° (MeOH-Me2CO); a 76.6-g. portion added during 15 min. with stirring into 750 cc. boiling H2O and 4.8 cc. concentrated H2SO4 and refluxed 15 min. gave I, m. 280° (decomposition) (H2O). I (15.7 g.), 41 g. NaNO2, and 297 g. CuSO4.5H2O in 18,000 cc. H2O kept 16 hrs. at room temperature, adjusted with dilute HNO3 to about pH 2.0, and extracted with AcOEt yielded the yellow 2-nitroimidazole (II) which was sublimed at 175°/0.5-1.0 mm. I (660 mg.), 1.6 g. NaNO2, and 40 cc. H2O kept 1 hr. at room temperature gave similarly II. 2-(p-Bromobenzeneazo)-4-methylimidazole (8.58 g.) in 200 cc. EtOH hydrogenated 4 hrs. at 14-21 atm./50° over 2 g. Raney Ni, and the crude product in H2O neutralized with 2.7 cc. 12N H2SO4 gave the 4-Me derivative (III) of I, m. 229-31° (1:10 H2O-EtOH); a 0.146-g. portion in I cc. H2O treated 21 hrs. at room temperature with 2.5 g. CuSO4.5H2O and 0.35 g. NaNO2 in 360 cc. H2O and adjusted with 1.5 cc. dilute HCl to pH 2.0 gave III. I (6.7 g.), 12.7 g. CuSO4.5H2O, and 460 cc. 12N H2SO4 treated at -20° with 69 g. NaNO2 in 80 cc. H2O (introduced under the surface of the mixture), kept 24 hrs. at room temperature, and adjusted with concentrated NH4OH to pH 0.5 gave II. CuSO4.5H2O (150 g.) in 2000 cc. H2O and then 79.2 g. I in 1000 cc. H2O added at 0° to 1600 cc. 12N H2SO4, cooled to -20°, treated (under the surface) with 828 g. NaNO2 in 3000 cc. H2O during 1 hr., kept 40 hrs. at room temperature, adjusted at -10° to pH 1.0 with about 5000 cc. concentrated NH4OH, and stirred 1-2 hrs. at 0° yielded II, m. 289° (decomposition). 1-Methyl-2-aminoimidazole-HCl (6.7 g.), 12.5 g. CuSO4.5H2O, and 800 cc. 12N H2SO4 treated at -20° with 69 g. NaNO2 in 160 cc. H2O and kept 40 hrs. at room temperature yielded 1-Me derivative of II, m. 102-3° (isoPrOH). 4,5-Dimethyl derivative of I gave similarly during 12 hrs. the 4,5-dimethyl derivative of II, which was sublimed at 100-10°/ 0.05 mm. 2-Aminobenzimidazole (13.3 g.) in 110 cc. 1.0N H2SO4 and 25 g. CuSO4.5H2O treated dropwise with stirring during 55 min. with 34.5 g. NANO2 in 100 cc. H2O at 0°, stirred 18 hrs. at room temperature, treated dropwise with cooling and stirring with 33 cc. 18N H2SO4, stirred 1.5 hrs. at room temperature, and extracted with 1000 cc. Et2O yielded 2-nitrobenzimidazole (IV), m. 261-2° (decomposition). IV (3.22 g.) in 10 cc. 2.5N NaOH and 20 cc. H2O treated dropwise with stirring at 55° with 3.0 cc. Me2SO4, stirred 1.5 hrs. at room temperature, and kept 12 hrs. gave the 1-Me derivative of IV, m. 166-8° (aqueous EtOH). 2-Amino-5,6-dimethylbenzimidazole (16.1 g.) in 100 cc. 1.0N H2SO4 and 25 g. CuSO4.5H2O treated dropwise with stirring at 0° with 34.5 g. NaNO2 in 100 cc. H2O gave similarly the 5,6-dimethyl derivative of IV, m. 244-5° (aqueous EtOH). Examples for the formulation of IV and some of its derivatives in tablets, capsules, suppositories, and injection solutions are given. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Computed Properties of 5709-67-1
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. Computed Properties of 5709-67-1
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem