Category: imidazoles-derivatives

Reference of 641571-11-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine 110 g (0.45 moles) of formula (XI) was dissolved in 1 L of chloroform. 4-methyl-3-nitro benzoyl chloride of the formula (IIA) prepared above was added slowly to the reaction mass at 10-15 C. for 60 minutes. Reaction mass was raised to room temperature and maintained for 4 hours. Reaction mass was filtered, washed with chloroform and dried.Yield: 161 g (87%) Purity: 99% (by HPLC) [0059] IR and NMR were consistent with the proposed structure.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala; Bhujanga Rao, Adibhatla Kali Satya; Rachakonda, Sreenivas; Gampa, Venugopala Krishna; Nannapaneni, Venkaiah Chowdary; US2013/210847; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, 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 46006-36-4, Formula: C8H6N2O2

B. (lH-Benzo[d]imidazol-4-yI)methanol.; lH-Benzo[d]imidazole-4- carboxylic acid (1.04 g, 6.41 mmol) was suspended in anhydrous tetrahydrofuran (80 mL) and cooled to -78 0C. A solution of lithium aluminum hydride in tetrahydrofuran (2.0M, 6.4 mL) was added via syringe. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was quenched with methanol and adsorbed onto silica gel. Flash chromatography (20% MeOH in EtOAc) afforded a white solid (550 mg, 3.72 mmol, 58%). MS (ESI) m/z 149.0 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzimidazole-7-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 57090-88-7, 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. 57090-88-7 name is 1H-Imidazole-4-carbonitrile, 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.

To a round bottom flask was added 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol), 2- bromopropane (794 mg, 6.44 mmol), and K2CO3 (890 mg, 6.44 mmol) in DMF (9 ml). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was filtered. The solvent was concentrated in vacuo. The residue was purified by prepHPLC to afford 310 mg of 1-Isopropyl-lH-imidazole-4-carbonitrile TFA salt and 71 mg of 3- isopropyl-3H-imidazole-4-carbonitrile TFA salt region-isomer.1-Isopropyl-lH-irnidazole-4-carboriitrile TFA salt was dissolved in EtOAc, washed with sat. NaHCO3, brine, dried under anhy. Na2SO4, filtered and concentrated to afford 200 mg of 1-isopropyl-l/Mrnidazole-4-carbonitrile as a colorless oil, m/z 136.5 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1072-63-5, These common heterocyclic compound, 1072-63-5, name is 1-Vinyl-1H-imidazole, 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.

Typically, 1,4-butanediyl-3,3?-bis-L-vinylimidazolium dibromide(BVD) was synthesized based on a reported method[94]. 1-Vinylimidazole (2.82 g, 30 mmol) was dissolved in15 mL ethanol, and 1,4-dibromobutane (3.24 g, 15 mmol) in15 mL ethanol was added dropwise to the 1-vinylimidazolesolution. The mixture was stirred at 60 C for 10 h. After cooling of the reaction flask to ambient temperature, the reaction mixture was added dropwise into 500 mL of drydiethyl ether. The white powder was separated and dried at room temperature.1,4-Butanediyl-3,3?-bis-L-vinylimidazolium dibromide(Mp = 148 C). 1H NMR (DMSO-d6, delta, ppm): 9.55 (2H),8.28 (2H), 7.93 (2H), 7.47 (2H), 5.92 (2H), 5.42 (2H), 4.30(4H), 1.82 (4H). 13C NMR (DMSO-d6, delta, ppm): 134.9,129.4, 123.8, 120.1, 109.2, 49.3, 26.4.

Statistics shows that 1-Vinyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-63-5.

Reference:
Article; Maleki, Maryam; Baghbanian, Seyed Meysam; Tajbakhsh, Mahmood; Journal of the Iranian Chemical Society; vol. 15; 2; (2018); p. 359 – 368;,
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

Some common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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. Application In Synthesis of 5-Bromo-1,2-dimethyl-1H-imidazole

Example 67: (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin-6-yl)bis(1,2-dimethyl-1H-imidazol-5-yl)methanol A solution of n-BuLi (2.5 M in hexanes, 0.24 mL, 0.6 mmol) was added dropwise by syringe to a solution of 5-bromo-l ,2-dimethyl-lH-imidazole (107.8 mg, 0.616 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, (4-chloro-3-(4-fluorobenzyl)-2-methoxyquinolin~6- yl)( 1 ,2-dimethyl- lH-imidazol-5-yl)methanone (0.217 g, 0.512 mmol, Intermediate 46: step b) in dry THF (2 mL) was added to the mixture via syringe. After 5 minutes, the reaction was removed from the cold bath and was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride. Water was added and the aqueous mixture was extracted with dichloromethane. The combined organic layers were dried (Na^SC ), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel 0-10% MeOH-DCM) to provide the title compound, NMR (400 MHz, CDC13) delta 8.23 (d, J = 2.2 Hz, 1H), 7.63 (d, J = 8.7 Hz, 1H), 7.37 (dd, J = 8.8, 2.1 Hz, i l l). 7.30 – 7.25 (m, 2H), 6.97 – 6.92 (m, 21 1). 6.19 (s, 1H), 6.12 (s, 21 1). 4.22 (s, 2H), 4.07 (s, 3H), 3.37 (s, 6H), 2.24 (s, 6H); MS m/e 520.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24134-09-6, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2302-25-2, name is 4-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromo-1H-imidazole

[00328] To a flask was added 4-bromo-5H-imidazole (approximately 455 mg, 3.1 mmol) in N-methylpyrrolidine (6 mL) and 3,5-difluoropyridine (366 mg, 3.1 mmol) and potassium carbonate (429 mg, 3.1 mmol). The reaction was heated at 100 C for 12 hours. LCMS showed the formation of the product. The reaction was filtered and the crude product was purified by reverse phase chromatography (CI 8 100 g column (ISCO);10-90% water/acetonitrile with a trifluoroacetic acid modifier) to afford purified product. The fraction were combined and neutralized with an SPE-CO3H cartridge to afford the desired product.

The synthetic route of 2302-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; COLLIER, Philip, N.; DAVIES, Robert, J.; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GOLDMAN, Brian, Anthony; GRILLOT, Anne-Laure; KOLPAK, Adrienne, Lynne; KRAUSS, Raul, Eduardo; LEDFORD, Brian; LIAO, Yusheng; MAGAVI, Sanjay, Shivayogi; MALTAIS, Francois; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; TANG, Qing; WANG, Tiansheng; (221 pag.)WO2018/106643; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, 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. Recommanded Product: 15965-54-5

Reference Example 52 5-Methoxy-2-chlorobenzimidazole (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g). NMR (CDCl3)delta: 1.60-2.00 (2H, m), 2.70 (2H, t, J=7Hz), 2.73 (3H, s), 2.83-3.23 (2H, m), 3.73 (3H, s), 4.30 (2H, s), 6.67-7.40 (6H, m), 12.50 (1H, br.) In a manner analogous to Reference Example 52, the same compounds as those obtained in Examples numbered between 35 and 156 were produced using appropriate starting materials.

The synthetic route of 2-Chloro-5-methoxy-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP239129; (1991); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 939-70-8, The chemical industry reduces the impact on the environment during synthesis 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, I believe this compound will play a more active role in future production and life.

General procedure: A 10%solution of NaOH (5 ml) in EtOH was added to a solutionof 2-acetylbenzimidazole (4) (1.6 g, 0.01 mol) in absoluteEtOH (20 ml) at 0C with stirring. Then the solution of anaromatic aldehyde (0.01 mol) in absolute EtOH (10 ml)was added dropwise. The reaction mixture was stirred for12 h at room temperature. After completion of reaction(monitored by TLC), the reaction mixture was poured ontocrushed ice. The separated solid was filtered off, washedwith water, and dried. The residue was purified by columnchromatography (silica gel, eluent 10% ethyl acetate inpetroleum ether) to afford pure benzimidazole-derived chalcone 5a-m.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(1H-Benzo[d]imidazol-2-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meshram, Gangadhar A.; Vala, Vipul A.; Chemistry of Heterocyclic Compounds; vol. 51; 1; (2015); p. 44 – 50; Khim. Geterotsikl. Soedin.; vol. 51; 1; (2015); p. 44 – 50,7;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1072-84-0, A common heterocyclic compound, 1072-84-0, name is 1H-Imidazole-4-carboxylic acid, molecular formula is C4H4N2O2, 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.

The nitroimidazole carboxylic acid was readily obtained by nitration of imidazole carboxylic acid (Scheme 2) as previously described [11,23].

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; Jean-Claude, Bertrand; US2012/283280; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem