Category: imidazoles-derivatives

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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Formula: C7H5ClN2

Step3: Under nitrogen protection,2-Chlorobenzimidazole (1.41 g, 9.2 mmol) was added to the reaction vessel.Phenylboronic acid (1.02 g, 8.4 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL, ethanol 20mL and distilled water 20mL,Stir at 120 ° C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, ethyl acetate was extracted, and the organic layer was dried over MgSO..The solvent was removed by distillation under reduced pressure.After purification by silica gel column chromatography, Intermediate 75-3 (1.22 g, 75percent) was obtained.

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (34 pag.)CN108409667; (2018); A;,
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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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methyl-1H-imidazole

General procedure: To a solution 5-bromo-1-methyl-(1H)-imidazole (180mg, 1.13 mmol) in THF (10 mL) HMPA (Hexamethylphosphoramide)was added (130 mg, 0.75 mmol) followed by t-BuLi (170 mg, 2.6 mmol) at -78oC, the resulted mixture wasallowed to stir at rt for 1 h. Then it was cooled back to -78oCand amidosulphone 4a-4j (0.75 mmol) was added in THF (5mL) slowly. The reaction mixture was slowly allowed to stirat rt for 2 h. Then, the reaction mixture was quenched withNH4Cl and extracted into EtOAc. The combined organiclayers were dried over Na2SO4 and distilled in vacuum to getcrude compounds 5a-5j and were purified by column chromatography using 5 % MeOH in DCM to get the final compounds5a-5j with 59-65 % yield.

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 1003-21-0.

Reference:
Article; Thripuram, Vijaya Durga; Bollikolla, Hari Babu; Mule, Siva Nagi Reddy; Battula, Sailaja Kumari; Ala, Vasu Babu; Letters in Organic Chemistry; vol. 15; 7; (2018); p. 569 – 574;,
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Reference of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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.

[0267] To a solution of 2-chloro-1H-benzo[d]imidazole (916 mg, 6 mmol) in 10 mL of dry DMF, which was cooled to 0 C., was careffilly added NaH (240 mg, 10.8 mmol) in small portions. The mixture was stirred for 15 minutes at this temperature. Then, methyl iodide (0.41 mL, 6.6 mmol) was added under continuous stirring for an additional 15 minutes. When thin layer chromatography (TLC) showed full conversion, the mixture was poured into 60 mL of water and a white solid precipitated. The precipitate was collected by filtration and dried in vacuo to obtain 2a 650 mg (65%) of pure product as a white solid. ?H NMR (400 MHz, DMSOd 5) oe 7.62-7.54 (m, 2H), 7.34-7.27 (m, 1H), 7.27-7.20 (m, 1H), 3.80 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; BAYLOR COLLEGE OF MEDICINE; O’Malley, Bert W.; Lonard, David Michael; Wang, Jin; Xu, Jianming; Chen, Jianwei; (47 pag.)US2017/290830; (2017); A1;,
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Synthetic Route of 57667-50-2, 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. 57667-50-2, name is 1-Propyl-1H-benzo[d]imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

1 ,3-bis(1 -Propyl-1 H-benzo[d]imidazol-2-yl)urea (1 9a) and 1 0-propyl-3-(1 -propyl-1 H-benzo[d]-imidazol2-yl)benzo[4,5]imidazo[1,2-a][1,3,5]triazine-2,4(3H,1OH)-dione (9b) were obtained in 8% (16.0 mg,0.045 mmol) and 12% (0.027 g, 0.067 mmol) yield respectively via a reaction of 1-propyl-1H- benzo[d]imidazol-2-amine (20a) (0.200 g, 1.141 mmol), 4-nitrophenylchloroformate (0.127 g, 0.628 mmol) and DIPEA (0.258 mL, 1.484 mmol) in CH2CI2 (4.0 mL) at room temperature. Reaction time 16h. 1,3-bis(1-Propyl-1H-benzo[d]imidazol-2-yl)urea (19a) White solid ; m.p. 178 o 1H-NMR (400 MHz, CDCI3): : 7.30-7.29(m, 2H), 7.13-7.09(m, 6H), 4.02(t, 4H, J= 7.20 Hz), 1.78(d, 4H, J= 7.60 Hz),0.88 (t, 6H, J = 7.60 Hz). 1 0-propyl-3-(1 -propyl-1 H-benzo[d]imidazol-2-yl)benzo[4,5]imidazo[1 2- a][1 ,3,5]triazine-2,4(3H,1OH)-dione (9b). Colorless solid; m.p. 222 C. 1H-NMR (400 MHz, DMSO-d6):: 8.01 (d, 1H, J = 7.60 Hz), 7.75 (d, 1H, J = 8.00 Hz), 7.71 -7.67 (m, 2H), 7.54-7.49 (t, 2H, J = 8.00 Hz), 7.41-7.28(m, 3H), 4.21-4.04(m, 4H), 1.91-1.81 (m, 2H), 1.79-1.69(m, 2H), 1.00(t, 3H, J= 7.20 Hz), 0.87 (t, 3H, J = 7.20 Hz).

The chemical industry reduces the impact on the environment during synthesis 1-Propyl-1H-benzo[d]imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; MAES, Bert; WYBON, Clarence; CHEN, Chen; BHEETER, Charles Beromeo; SERGUEEV, Serguei; (88 pag.)WO2017/46133; (2017); A1;,
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Synthetic Route of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 0.351 g of imidazole-2-carboxylic acid (3.13 mmol) in 15 ml DMF were added 0.508 g of CDI (3.13 mmol) and 0.43 ml triethylamine (3.13 mmol), and the mixture stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (2.4 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and trying 0.42 g 1H-Imidazole-2-carboxylic acid [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-amide (57%) were obtained as a yellow solid; M.p.: 227-228 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Imidazolecarboxylic acid, its application will become more common.

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
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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. 15965-31-8, name is 5-Chloro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

A stirred suspension of 4-chloro-lH-imidazole (9.75 mmol, 1.0 g) , 2-chloro-5-nitropyridine (9.75 mmol, 1.54 g) and potassium carbonate (11.70 mmol, 1.61 g) in DMF (10 mL) was heated at 80 C for 3 hours. The mixture was cooled to room temperature and water was added. The resulting precipitate was filtered, washed with water and dried to give crude 6- ( 4-chloroimidazol-l-yl ) -3- nitropyridine (1.94 g, 89%).

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
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These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-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. COA of Formula: C4H5BrN2

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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Imidazole | C3H4N2 – PubChem

Reference of 7152-24-1,Some common heterocyclic compound, 7152-24-1, name is 2-(Methylthio)benzimidazole, molecular formula is C8H8N2S, 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.

EXAMPLES Synthesis of Compound 1 A suspension of 164 g (1.0 mol) of 2-methylthiobenzimidazole (manufactured by Tokyo Kasei Co. or Aldrich Co.) in 1500 ml of water was prepared. To it were added 1.65 g (0.005 mol) of sodium tungstate dihydrate and 280 ml of 35% aqueous hydrogen peroxide. The mixture was placed in a water bath of 50 C. and stirred for 6 hours. During this period, 181 g of 2-methanesulfonylbenzimidazole precipitated and was collected by filtration.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Methylthio)benzimidazole, its application will become more common.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US5097042; (1992); A;,
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Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 496-46-8 as follows. Recommanded Product: 496-46-8

Preparation tetranitro glycoluril: equipped with a reflux condenser, a thermometer, a stirrer, pressure-equalizing dropping funnel, the reaction 3000ml four-necked round flask, 500ml of fuming nitric acid.When the temperature to about 10 , 20g glycoluril added rapidly, stirred to dissolution, to give glycoluril – fuming nitric acid solution; the glycoluril – nitric acid solution is sent down to the temperature of the smoke 0 ~ 5 , 250ml of acetic anhydride was added dropwise, drops added maintaining the temperature at 0 ~ 5 ; acetic anhydride addition was completed, the nitration temperature is maintained at 0 ~ 5 , nitration reaction after 4h, the temperature raised to nitration 5 ~ 10 , 3H continued nitration; nitrated using a temperature gradient to gradually warm ,, 5 gradient for 2 hours and then raised 5 , nitration began maintaining the temperature at 0 deg.] C, nitration reaction 2h, 5 increased, i.e., the temperature was raised 5 nitration, nitration continued 2h, then increased 5 , i.e. nitration temperature was raised to 10 , maintained for 3 hours.10min nitration reaction bottle with a precipitate beginning, gradually warming nitration temperature gradient, the amount of precipitation as the reaction temperature, the reaction time increased, the precipitation was complete, the reaction mixture was lowered vial -10 ~ 0 , the reaction was stopped, the bottle within fritted funnel mixture was filtered, the white solid was washed with tetranitromethane glycoluril dichloromethane to large neutral stand soaked in dichloromethane

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hubei Aerospace Institute of Chemical Technology, CASC; Ha, HengXin; (8 pag.)CN105777575; (2016); A;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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: 39021-62-0

To a cloudy mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (290.5 mg, 0.823 mmol, Intermediate 1: step c) and 1-methyl-1H-imidazole-5-carbaldehyde (90.6 mg, 0.823 mmol) in THF (8 mL) under nitrogen at -78 C. was added n-BuLi (1.6 M in hexane, 0.643 mL, 1.03 mmol) dropwise. The resulting solution was stirred at -78 C. for 3 hours, then was warmed to 0 C. for 15 minutes before addition of saturated aqueous NH4Cl to quench. The mixture was diluted with water and was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-6% MeOH-DCM) to afford the title compound as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-62-0, 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.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem