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. 1072-62-4, name is 2-Ethyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Ethyl-1H-imidazole

General procedure: To a solution of (benzofuran-2-yl)(phenyl)methanol 4 (224 mg, 1 mmol) in dichloromethane (50 mL) was added methanesulfonyl chloride (1.2 mmol) and triethylamine (2 mmol) at 0 oC. The resulting mixture was stirred at room temperature for 12 h. After quenching the reaction with water (50 mL), the layers were separated. The organic phase was dried over anhydrous Na2SO4 and concentrated, and used for the next synthetic step. A mixture of the previous methanesulfonate and imidazole or substituted imidazole (3 mmol) was stirred in acetonitrile (20 ml) at reflux for 24-48 h (monitored by TLC). After cooling to room temperature, the solvent was concentrated, and the residue was diluted with EtOAc (20 mL). The organic layer was washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether 60-90 oC : ethyl acetate = 3:1?1:1) to afford 6-9 in 60-75% yield (two steps) as yellow oil or powder.

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; Wang, Xue-Quan; Liu, Lan-Xiang; Li, Yan; Sun, Cheng-Jun; Chen, Wen; Li, Liang; Zhang, Hong-Bin; Yang, Xiao-Dong; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 111 – 121;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 312-73-2, 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. 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Compound II (60.00g, 0.322mol, 1.0eq.) And potassium carbonate (89.01g, 0.644mol, 2.0eq.) Were added to 600mL DMF, and iodomethane (91.4g, 0.644mol, 2.0eq) was added dropwise at 0 C. .), After the addition was completed, the reaction was performed at 25 C for 1h. TLC showed that the raw materials had reacted. The system was poured into 1L of ice water, washed with water (100mL * 2), filtered to obtain a white solid, washed with water (100mL * 2), white solid Dissolved in ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to give compound III-1 as a white solid 62.00g, yield: 97.1%

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, 2-(Trifluoromethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Yaoshi Technology Co., Ltd.; Wang Zhengjiang; Xia Aihua; (15 pag.)CN110903245; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10111-08-7,Some common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, molecular formula is C4H4N2O, 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.

Step a: 1-Benzyl-1H-imidazole-2-carbaldehydeTo a solution of the compound 1H-imidazole-2-carboxaldehyde (5 g, 52.0 mmol) in methanol (20 mL) was added acetone (40 mL), potassium carbonate (21.56 g, 156.2 mmol) and tetrabutyl ammonium bromide (catalytic amount). The reaction mixture was stirred at room temperature for 1 hour followed by the addition of benzyl bromide (8.9 g, 52.0 mmol). The reaction mixture was stirred at room temperature for 4 hours. The mixture was filtered through sintered funnel and the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by column chromatography using 0.5% methanol in dichloromethane to furnish the title compound.

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

Reference:
Patent; Kumar, Naresh; Kaur, Jaskiran; Ray, Abhijit; Gupta, Suman; Malhotra, Shivani; Shirumalla, Rajkumar; US2010/144801; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General method: Benzimidazole-2-thiol (7) (1 eq) and pertinent acid chloride or acid anhydride (1.1 eq) were dissolved in pyridine (4.4 eq) under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. After quenching with water (10-25 ml), ethyl acetate (30-45 ml) was added. The organic phase was extracted with 3M hydrochloric acid (3 × 25 ml), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified as stated below.

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, 2-Mercaptobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Braun, Stephan; Botzki, Alexander; Salmen, Sunnhild; Textor, Christian; Bernhardt, Guenther; Dove, Stefan; Buschauer, Armin; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4419 – 4429;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 641571-13-3, 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 641571-13-3 as follows.

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid (12 mg, 0.0436 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (22.6 mg, 0.059 mmol), and TEA (7.2 mg, 0.078 mmol) were dissolved in DMF (0.2 ml), the solution was stirred at 45 C. for 30 minutes, the compound F (10.2 mg, 0.039 mmol) was then added, and the solution was stirred at 45 C. for 12 hours. After the reaction was completed, ethyl acetate was added and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was crystallized to obtain a target compound 3-(4-methyl-1H-imidazol-1-yl)-N-(3-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)-5-(trifluoromethyl)benzamide (15.6 mg, 78%). 1H NMR (400 MHz, DMSO-d6) delta 10.71 (1H, s), 10.53 (1H, s), 8.49 (1H, s), 8.43-8.42 (2H, m), 8.26 (1H, s), 8.22 (1H, s), 8.06 (1H, dd, J=8.2, 1.4 Hz), 7.79 (1H, d, J=8.0 Hz), 7.73 (1H, s), 7.58-7.54 (2H, m), 7.04 (1H, d, J=4.0 Hz), 3.61 (2H, s), 2.20 (3H, s). (Exact mass 509.11, m/z 510.1186)

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Industry-University Cooperation Foundation Hanyang University ERICA Campus; HAH, Jung-Mi; LEE, Jung Hun; KIM, Minjung; (30 pag.)US2018/37589; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 96797-15-8, name is 4-Iodo-1-trityl-1H-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 96797-15-8, category: imidazoles-derivatives

[270] To a solution of (2-forrnylphenyl)boronic acid (2.0 g, 13.3 rnrnol) in a rnixed solvent of N,N- dirnethylforrnarnide (DMF) (60 rnL) and water (12 rnL) was successively added 4-iodo-1- trityl-1H-irnidazole (6.1 g, 14.0 rnrnol), and potassiurn phosphate (5.6 g, 26.6 rnrnol). After degassing with nitrogen, the resulted rnixture was added tetrakis(triphenylphosphine)palladiurn(0) (Pd(PPh3)4) (300 rng, 0.26 rnrnol). The resulted rnixture was degassed with nitrogen and stirred at 90C for overnight under nitrogen. And then the rnixture was cooled down to roorn ternperature and filtered, the filtrate was added water (60 rnL), extracted with ethyl acetate (100 rnLx2). The cornbined organic phase was washed with brine (25 rnL), dried over sodiurn sulfate, filtered and concentrated. The residue was purifiedby colurnn chrornatography on silica gel (petroleurn ether: ethyl acetate= 6:1) to afford cornpound 1.1 (3.3 g, yield: 60%) as a white solid.[271] rn/z: [M+H]415

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, 4-Iodo-1-trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO.,LTD.; LI, Qun; GAO, Daxin; (158 pag.)WO2016/131380; (2016); 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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3IN2

4(5)-Monoiodoimidazole (3.8 g, 19.3 mmol) and compound 4 (3.4, (4.1 g, 23.2 mmol) were dissolved in anhydrous CH3CN (150 mL) under inert atmosphere. N,0-bis(trimethylsilyl) acetamide (28.6 ml, 115.8 mmol) was added. The reaction mixture was stirred at rt for 5 h, and then cooled to 0C. Trimethylsilyl triflouromethane sulfonate (5.7 mL, 25.6 mmol) was added slowly and then the solution was heated to 90C and stirred for 12 h. The reaction mixture was quenched by addition of aq. NaHC03 (30 mL) and stirred for 30 min. The solution was separated and the aqueous layer was extracted with CH2CI2 (2 x 50 mL). The organic layers were combined, washed with H20 (3 x 50 mL) and brine (50 mL), and dried over MgS04. The solvent was removed under reduced pressure. The resultant syrup was purified by flash chromatography over silica gel to obtain yellow syrup 18. (346 mg, 6%). 1H NMR (CDC13, 400 MHz): delta 7.38 (1H, d, J = 0.92 Hz), 7.01 (1H, d, J = 0.88 Hz), 5.14 (2H, s), 3.95 (2H, t, J = 4.6 Hz), 3.45 (2H, t, J = 4.6 Hz) 1.84 (3H, s). 13C NMR (CDC13, 100 MHz): delta 170.8, 139.2, 124.6, 82.7, 76.4, 66.8, 62.8, 20.9. NMS calcd for C8HiiIlN203 310.9, found 311.0[M + H+].

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; UNIVERSITY OF MARYLAND, BALTIMORE COUNTY; KATHOLIEK UNIVERSITEIT LEUVEN; LIEDEN UNIVERSITY MEDICAL CENTER; RADTKE, Katherine, L.; PETERS, Hannah, L.; NEYTS, Johan; JOCHMANS, Dirk; SNIJDER, Eric, J.; (33 pag.)WO2016/123318; (2016); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-62-4, 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. 1072-62-4, name is 2-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-(2-Ethyl-imidazol-1-yl)-pyrimidine-5-carboxylic acid cyclopropyl-piperidin-4-yl-amide A mixture of 4-[(2-chloro-pyrimidine-5-carbonyl)-cyclopropyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (3.0 g), 2-ethylimidazole (0.73 g) and ethyldiisopropylamine (2.0 mL) in N-methyl-2-pyrrolidinone (10 mL) is stirred for 12 h at 80 C. The solvent is removed in vacuo and the residue is purified by HPLC (C18 RP Sunfire, H2O/MeOH+0.1% TFA) to yield the boc-protected intermediate. The intermediate is dissolved in dichloromethane and dichloromethane/trifluoroacetic acid (1:1, 5% H2O) is added and the mixture is stirred for 5 h at room temperature. After concentration in vacuo the residue is triturated with diethyl ether to afford the title compound as a trifluoroacetic acid salt. LC (method 10): tR=1.56 min; Mass spectrum (ESI+): m/z=341 [M+H]+.

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

Reference:
Patent; Neurocrine Biosciences, Inc.; Boehringer Ingelheim International GmbH; NOSSE, Bernd; ECKHARDT, Matthias; HIMMELSBACH, Frank; LANGKOPF, Elke; ASHWEEK, Neil J.; HARRIOTT, Nicole; US2014/45823; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1402838-08-7, 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

2-(1-trityl-1H-imidazol-5-yl)benzaldehyde (0105-1) (200 mg, 0.483 mmol, 1 eq),Compound ((5-(2-(dimethoxyphosphoryl)acetyl)benzofuran-2-yl)methyl) tert-butyl carbonate (0207-50) (211 mg, 0.531 mmol, 1.1 eq.) withCesium carbonate (314 mg, 0.966 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and filtered to give the target product (305 mg, yield: 92.14%) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 2-(1-Trityl-4-imidazolyl)benzaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67085-11-4,Some common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

Take 5kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1-hydro-imidazole,Fully dissolved in 35 kg of methylene chloride and added at a rate of 1.5 ml/s at 20C5kg of thionyl chloride was slowly warmed to 32C and the reaction was incubated for 1 hour.Then reflux at 60 C for 1 hour, slowly cooled to 15 C to obtain the reaction solution;In the reaction solution, 10 C. water was added at a rate of 0.5 ml/s with stirring, the volume ratio of the reaction solution to water was 0.005:1, and anhydrous sodium carbonate was added at 1.0-1.5 kg/L. Suction filtrationSolid, the liquid was concentrated at 55 C until the dichloromethane evaporated, and dried.This yields 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole with a purity of 99.17%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, its application will become more common.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Li Sanxin; Peng Kaifeng; Ling Yonggen; Wen Fengqiu; Gong Yun; Li Fujun; (13 pag.)CN105198818; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem