Month: November 2022

On January 8, 1966, Lebedev, O. V.; Epishina, L. V.; Sevost’yanova, V. V.; Novikova, T. S.; Khmel’nitskii, L. I.; Novikov, S. S.; Prikhod’ko, A. S. published a patent.Application In Synthesis of 2-Nitro-1H-benzo[d]imidazole The title of the patent was 2-Nitroimidazoles. And the patent contained the following:

The title compounds are prepared by treating 2-amino derivatives of imidazole with an aqueous solution of Cu(NO2)2 and NaNO2 at a temperature of ∼60°. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Application In Synthesis 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. Application In Synthesis of 2-Nitro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

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

Beaman, Alden G.; Tautz, William; Gabriel, Thomas; Keller, Oscar; Loome, Voldemar; Duschinsky, Robert published an article in 1965, the title of the article was Studies in the Nitroimidazole series. I. Synthesis of azomycin and related compounds.Reference of 2-Nitro-1H-benzo[d]imidazole And the article contains the following content:

Azomycin (2-nitroimidazole) was synthesized in 50% yield by treatment of 2-aminoimidazole with HONO in the presence of CuSO4 (Jones and Robins, CA 55, 559c). Synthetic azomycin was identified with natural azomycin by mixed m.p., by Pka, by uv and ir and by its in vitro anti-bacterial spectrum against 19 microorganisms. The method was also applied to the preparation of alkyl-2-aminoimidazoles and to 2-aminobenzimidazoles. The resulting 2-nitro compounds were then alkylated in the 1-position. When treated with alkali, the 1-alkyl-2-nitroimidazoles were more stable than the 1-alkyl-2-nitrobenzimidazoles which were transformed into 2-benzimidazolinones. The compounds were tested microbiol. by agar diffusion-cup plate employing a complex nitrogenous medium. Growth inhibition characteristics for the various compounds against a number of bacteria were given. 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

Grunberg, E.; Titsworth, E. published an article in 1965, the title of the article was Toxicity and antitrichomonad activity of 2-nitroimidazole and 2-nitrobenzimidazole derivatives.Formula: C7H5N3O2 And the article contains the following content:

2-Nitroimidazole, 2-nitrobenzimidazole, and their alkyl, alkoxy, and chloro derivatives were generally moderately to highly toxic in mice. Only 1,4,5-trimethyl-2-nitroimidazole and 5,6-dimethyl-2-nitrobenzimidazole were relatively atoxic. 2-Nitroimidazole and certain of its Me derivatives were active orally against Trichomonas foetus infection in mice as well as subcutaneously against local T. vaginalis infection in mice. The 1-allyl derivative was inactive orally against T. foetus, but did show activity by both the subcutaneous and oral routes against T. vaginalis. 2-Nitrobenzimidazole and its alkyl, alkoxy, and chloro derivatives were without oral activity against either T. vaginalis or T. foetus. The majority of the 2-nitrobenzimidazole derivatives tested showed slight to moderate activity subcutaneously against local T. vaginalis infection of mice. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Formula: C7H5N3O2

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. Formula: C7H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

On March 13, 1967, Pozharskii, A F.; Zvezdina, E. A.; Simonov, A. M. published a patent.Quality Control of 2-Nitro-1H-benzo[d]imidazole The title of the patent was Simultaneous preparation of 2-nitrobenzimidazole and 2,2′-azobenzimidazole. And the patent contained the following:

1-Benzyl-2-aminobenzimidazole is treated with an excess of Na in liquid NH3 at -70° followed by separation of 2,2′-azobenzimidazole by acidifying with concentrated HCl, filtrating, acidifying the filtrate, and purifying the product. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Quality Control 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. Quality Control of 2-Nitro-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Pozharskii, A. F.; Zvezdina, E. A.; Simonov, A. M. published an article in 1966, the title of the article was Synthesis of 2-nitrobenzimidazole (benzazomycin).Recommanded Product: 5709-67-1 And the article contains the following content:

Reaction of 1-benzyl-2-aminobenzimidazole with 4 g. at. Na in liquid NH3 gave 43% 2-nitrobenzimidazole, decomposed at 258°, and 55% 2,2′-azobenzimidazole (I), red-orange, m. above 350°. With 2 g. atoms Na the reaction gave 32% azo compound and 60% 2-aminobenzimidazole, m. 226.5°. When air is totally excluded, the latter is formed in 78% yield as the sole product. The di-Na derivative of aminobenzimidazole is very easily attacked by air to form the above oxidation products, both of which gave the amino derivative after reduction with Sn-HCl. The nitro derivative was devoid of basic properties and was acidic as it readily formed a Na salt which was easily alkylated in the 1-position. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Recommanded Product: 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. Recommanded Product: 5709-67-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Pozharskii, A. F.; Zvezdina, E. A.; Simonov, A. M. published an article in 1967, the title of the article was Unexpected formation of 2-nitro- and 2,2′-azobenzimidazoles.Related Products of 5709-67-1 And the article contains the following content:

Readily accessible 1-benzy-2-aminobenzimidazole (I) (CA 55: 16520f) treated with 2 moles Na in liquid NH3 yielded 60% of the expected 2-aminobenzimidazole (II) and 32% orange-red 2,2′-azobenzimidazole (III), m. >350°. With 4 moles Na in liquid NH3, 43% 2-nitrobenzimidazole (IV), m. 258°, and 55% III were produced. The structures of III and IV were established by reduction with Sn and HCl to II. IV is strongly acidic and gives a stable Na salt, m. 350°, readily alkylated to 1-alkyl-2-nitrobenzimidazoles. III is less acidic than IV and this facilitates their separation I is debenzylated with Na in liquid NH3 to give disodio (V) and trisodio (VI) derivatives, which when oxidized by atm. O gave III and IV. Treatment of I with 4 moles Na in liquid NH3 in a stream of dry N yielded 78% II. Treatment of 1-methyl- and 1-ethyl-2-aminobenzimidazoles with 4 moles Na in liquid NH3 gave only 1.5 and 0.7% of the corresponding 2,2′-azo derivatives, m. 289-90° (alc.) and 197° (EtOAc), resp. Sodio derivatives from 1-alkyl-2-aminobenzimidazoles gave the corresponding azo products only on long contact with air. The experimental process involved the reaction of 2-Nitro-1H-benzo[d]imidazole(cas: 5709-67-1).Related Products of 5709-67-1

The Article related to azobenzimidazoles, benzimidazoles, anti-infective agents, azo compounds, benzimidazoles, chemical phenomena, chemistry, chemistry, organic, nitrobenzenes, organic chemistry phenomena and other aspects.Related Products of 5709-67-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem