Month: August 2021

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

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

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

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

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 37052-78-1,Some common heterocyclic compound, 37052-78-1, name is 5-Methoxy-1H-benzo[d]imidazole-2-thiol, molecular formula is C8H8N2OS, 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.

[Reference Example 7] Production of 4-(5-methoxybenzimidazole-2-ylthio)butanoate ester hydrogen bromide salt 6.48 g (33.2 mmol) of 4-bromobutanoate ethyl ester were added to 10 ml of an ethanol solution containing 5.0 g (27.7 mmol) of 5-methoxybenzimidazole-2-thiol followed by stirring for 1 hour at 80C and adding 90 ml of ethyl acetate. The reaction solution was returned to room temperature and the formed crystals were filtered out followed by drying to obtain 9.34 g of the target compound (yield: 90%). 1H-NMR (270 MHz, CDCl3) (ppm): 7.65 (d,1H,J=8.91 Hz), 7.24 (S,1H), 7.00 (dd,1H,J=2.43, 8.91 Hz), 4.21 (q,2H,J=7.29 Hz), 3.83 (s,3H), 3.74 (m,2H), 2.61 (m,2H), 2.10 (m,2H), 1.30 (t,3H,J=7.29 Hz)

The synthetic route of 37052-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEIJIN LIMITED; EP1249450; (2002); 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 2-(1-Trityl-4-imidazolyl)benzaldehyde

step 1.312 mg of compound 22 was dissolved in 10 ml of tetrahydrofuran.Add 414 mg of compound 26,Add 2 drops of acetic acid dropwise, react at room temperature until the starting reaction is complete.Squeeze off most of the THF under reduced pressure, add water and ethyl acetate.The organic phase was separated, the organic phase was washed with saturated NaCI solution and dried over anhydrous NaSO4, Obtaining compound 32,Directly invest in the next step;

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Huawei Pharmaceutical Development Co., Ltd.; Zhang Xiaoqing; Song Zhichun; Bao Jinyuan; (52 pag.)CN108689958; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, Product Details of 39021-62-0

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (3.0 g, 6.97 mmol, Intermediate 5: step d) was added THF (40 mL) and the solution was cooled to -70 C. n-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was then added dropwise. After 2 minutes, 1-methyl-1H-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C. bath. After 35 minutes the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc:THF (10:2, 5*50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. Chromatography on silica gel (30% acetone-DCM increasing to 5% MeOH) provided the title compound.

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-Methyl-1H-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1977-72-6, These common heterocyclic compound, 1977-72-6, name is 5-Fluoro-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.

CuBr 6 mg (0.04 mmol), TEMPO 5 mg (0.03 mmol), compounded in a 25 mL Schlenk reaction tube5-fluorobenzimidazole 55 mg (0.4 mmol),28 mg (0.2 mmol) of salicylic acid (0.2 mmol) and p-xylene (0.5 mL), followed by 33 muL of pyridine (0.4 mmol) were added and the reaction was stirred at 120°C for 36 hours under reflux.Cool to room temperature, transfer all to a 25 mL flask, spin off the solvent on a rotary evaporator, add an appropriate amount of silica gel to spin dry, and then use a 300-400 mesh silica gel column. The developing solvent used is petroleum ether:ethyl acetate=16: 1 to 6:1, that is, compound III-6 15 mg, yield 30percent, white solid

Statistics shows that 5-Fluoro-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 1977-72-6.

Reference:
Patent; Southwest University; Cai Guixin; Xie Dan; (14 pag.)CN107955020; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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: 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde

2-Methyl-2-butene (5.0 mL), sodium dihydrogenphosphate dihydrate (1.55 g) and sodium chlorite (3.14 g) were added to a solution containing 4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde (2 g) in water (10 mL) and tert-butanol (30 mL), and the reaction solution was stirred for two hours. The generated solid was collected by filtration to obtain the title compound (745 mg). The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 3.89 (s, 3H), 7.09 (s, 1H), 7.54 (m, 2H), 7.63 (dd, J = 8.0, 1.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 8.05 (s, 1H).

The synthetic route of 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2019093; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem