Category: 10597-52-1

Application of 10597-52-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 10597-52-1 name is 7-Nitro-1H-benzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step B: Preparation of tert-butyl 4-nitro-1H-benzo[d]imidazole-1-carboxylate: Triethylamine (1.03 mL, 7.36 mmol) was added to a suspension of 4-nitro-1H-benzo[d]imidazole (1.0 g, 6.13 mmol) in dichloromethane (50 mL), followed by addition of Boc2O (1.61 g, 7.36 mmol). The reaction was stirred at room temperature for 16 hours and then quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (50 mL*3), and the combined organics were dried, filtered and concentrated. The crude product was purified by flash column chromatography, eluding with hexanes/ethyl acetate (4:1) to give the desired product (1.50 g, 93%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Nitro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Nitro-1-(3-nitrophenyl)benzimidazole was prepared analogueously to 3 g from 4-nitrobenzimidazole and 1-fluoro-3-nitrobenzene. Mp 260-262 C. 1-(3-Aminophenyl)-4-nitrobenzimidazole was prepared from 4-nitro-1-(3-nitrophenyl)benzimidazole as described in Example 3a. Mp 159-161 C.

The synthetic route of 10597-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NeuroSearch A/S; Meiji Seika Kaisha, Ltd.; US5554630; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10597-52-1, A common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a suspension of sodium hydride (0.014 g, 0.607 mmol) in dry DMF (5 mL) under Ar in an ice bath was added solid Intermediate 15 (0.090 g, 0.552 mmol) in one portion, and then the ice bath was removed. After 30 minutes at room temperature, the reaction was returned to an ice bath, then ethyl iodide (0.049 ml, 0.607 mmol) added dropwise, and the reaction stirred cold. The bath was removed, and the reaction stirred at room temperature for 12 hours, then heated to 65 C. The reaction was concentrated, taken up in EtOAc and washed five times with brine, filtered through cotton, dried (Na2SO4), filtered, and concentrated. The resulting brown oil was purified by flash column chromatography (Silica gel, 0-60% EtOAc/Heptane). The product fractions were concentrated to yield the title compound.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, molecular formula is C7H5N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 10597-52-1

To a stirred suspension of sodium hydride (665 mg, 16.64 mmol) in DMF (90 mL) at rt was added 4-nitro-1H-benzimidazole (2714 mg, 16.64 mmol) in several portions. After stirring for 1 h, 4-fluorobenzonitrile (1350 mg, 11.146 mmol) was added and the mixture was stirred for 15 h at 130C. After cooling, water was added, the precipitate was filtered off, washed with water and dried to yield 4-(4-nitro-benzoimidazol-1 -yl)-benzonitrile (2.47 g, 47.76 %).1H-NMR (300 MHz, d6-DMSO): delta =8.92 (1H), 8.16 8.11 (3H), 8.08 (1H), 7.97 (1H), 7.95 (1H), 7.53 (1H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10597-52-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KLAR, Ulrich; KOPPITZ, Marcus; NGUYEN, Duy; KOSEMUND, Dirk; NEUHAUS, Roland; SIEMEISTER, Gerhard; WO2012/130905; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 10597-52-1, Product Details of 10597-52-1

4-Nitrobenzimidazole (41.7 mmoles, 6.8 g) was dissolved in 200 ml DMF. Sodium hydride (47.5 mmoles, 1.9 g of 60% in mineral oil) was added portionwise. The reaction was stirred for 30 minutes. Ethyl 2-bromooctanoate was added. The reaction stirred at room temperature for 3 hours and concentrated. Ethyl acetate and water were added; and the layers separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The intermediate was purified by HPLC over silica gel eluted with a gradient of 0-50% ethyl acetate in hexane. The reaction yielded 10.3 g of ethyl 2-(4-nitro-1H-benzimidazol-1-yl) octanoate. (MS) M. Pt.: 86-89 C. Calculated for C17 H23 N3 O4: C, 61.25; H, 6.95; N, 12.60. Found: C, 61.52; H, 7.06; N, 12.21.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eli Lilly and Company; US5612360; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 10597-52-1, Product Details of 10597-52-1

4-Nitrobenzimidazole (41.7 mmoles, 6.8 g) was dissolved in 200 ml DMF. Sodium hydride (47.5 mmoles, 1.9 g of 60% in mineral oil) was added portionwise. The reaction was stirred for 30 minutes. Ethyl 2-bromooctanoate was added. The reaction stirred at room temperature for 3 hours and concentrated. Ethyl acetate and water were added; and the layers separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The intermediate was purified by HPLC over silica gel eluted with a gradient of 0-50% ethyl acetate in hexane. The reaction yielded 10.3 g of ethyl 2-(4-nitro-1H-benzimidazol-1-yl) octanoate. (MS) M. Pt.: 86-89 C. Calculated for C17 H23 N3 O4: C, 61.25; H, 6.95; N, 12.60. Found: C, 61.52; H, 7.06; N, 12.21.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eli Lilly and Company; US5612360; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 7-Nitro-1H-benzo[d]imidazole

(Step 1) tert-Butyl 4-nitro-1H-benzimidazole-1-carboxylate To a suspension of 4-nitro-1H-benzimidazole (2.65 g) in tetrahydrofuran (80.0 mL), triethylamine (3.38 mL) and di-tert-butyl dicarbonate (4.25 g) were added, and the mixture was stirred at room temperature for 1 hour. 4-Dimethylaminopyridine (0.0397 g) was then added to the mixture, and the resultant mixture was stirred at room temperature overnight. After the reaction solution was concentrated under reduced pressure, the residue obtained was purified by silica gel column chromatography (chloroform/ethyl acetate). After concentration under reduced pressure, diethyl ether was added to the solid obtained to obtain a suspension, and the suspension was filtered off and dried to obtain the title compound (3.94 g) as a solid. 1H-NMR (CDCl3) delta: 1.73 (9H, s), 7.53 (1H, t, J = 8.2 Hz), 8.20-8.22 (1H, m), 8.39-8.41 (1H, m), 8.62 (1H, s). MS (m/z) :164 (M-CO2tBu+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10597-52-1.

Reference:
Patent; Daiichi Sankyo Co., Ltd.; NAITO, Hiroyuki; KAGOSHIMA, Yoshiko; FUNAMI, Hideaki; NAKAMURA, Akifumi; ASANO, Masayoshi; HARUTA, Makoto; SUZUKI, Takashi; WATANABE, Jun; KANADA, Ryutaro; HIGUCHI, Saito; ITO, Kentaro; EGAMI, Akiko; KOBAYASHI, Katsuhiro; EP3643703; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 7-Nitro-1H-benzo[d]imidazole

To a stirred suspension of benzimidazole 34 (4.11 g, 30.6 mmol) in 230 mL of CH3CN was added BSA (8.22 mL,39.8 mmol), and the solution was stirred for 10 min during which time the reaction mixture became homogenous. TAR (9.65 g, 39.8 mmol) was added followed by TMSOTf (5.88 mL, 38.8 mmol) and the reaction was heated to reflux for 3 h before being cooled to rt and diluted with 200 mL of EtOAc. The organic layer was washed with 200mL of satd. NaHCO3 and 200 mL of brine. The organic layer was then dried (Na2SO4), filtered, and concentrated in vacuo to afford a yellow oil. The oil was purified by flash chromatography (0-20% MeOH/DCM) to afford the triacetate 35

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Brockway, Anthony J.; Volkov, Oleg A.; Cosner, Casey C.; MacMillan, Karen S.; Wring, Stephen A.; Richardson, Thomas E.; Peel, Michael; Phillips, Margaret A.; De Brabander, Jef K.; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5433 – 5440;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Nitro-1H-benzo[d]imidazole

A 500-mL round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet is charged with compound 3b (3.30 g, 30.6 mmol), potassium carbonate (8.95 g, 64.8 mmol), anhydrous DMF (200 mL) and 4-chloromethylpyridine hydrochloride (3.98 g, 24.3 mmol) and the mixture is then stirred under nitrogen for 24 h at ambient temperature. After such time the reaction is partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer is separated and extracted with ethyl acetate (6¡Á250 mL). The combined organic extracts are dried with sodium sulfate, and the drying agent is filtered off. The filtrate is then concentrated under vacuum to give a brown solid, which is purified by column chromatography to afford compound 3c as a yellow solid.

The synthetic route of 10597-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitchell, Scott A.; Danca, Mihaela Diana; Blomgren, Peter A.; Brittelli, David R.; Zhichkin, Pavel; Voss, Matthew E.; US2006/270702; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem