Category: imidazoles-derivatives

Related Products of 570-22-9, A common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

General procedure: The complex was synthesized by hydrothermal method. A mixture of Zn(NO3)2.6H2O (0.47 g; 1.6 mmol), H3idc (0.25 g, 1.6 mmol) and water (30 mL) was sealed in a 45 mL Parr brand teflon-linedacid digestion bomb and heated at 180 C for 5 days, and then cooled to room temperature at a rate of 5 C/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:
Article; Erer, Hakan; Ye?ilel, Okan Zafer; ?ahin, Onur; Bueyuekguengoer, Orhan; Inorganica Chimica Acta; vol. 434; (2015); p. 14 – 23;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 615-16-7, The chemical industry reduces the impact on the environment during synthesis 615-16-7, name is 2-Hydroxybenzimidazole, I believe this compound will play a more active role in future production and life.

Step 1: (0389) 1H-benzimidazol-2(3H)-one 19-a (500 mg, 3.73 mmol) was added into anhydrous aluminum chloride (1.98 g, 14.9 mmol) and tetrachloroethane (3 ml). Chloroacetyl chloride (843 mg, 7.46 mmol) dissolved in tetrachloroethane (3 ml) was added dropwise thereto under ice bath followed by stirring at 100 C. for 1 hour. The mixture was cooled to room temperature, ice and 4N hydrochloric acid (20 ml) were added sequentially followed by stirring for 6 hours, the precipitated solid was filtered, the filter cake was slurried in isopropanol, filtered, and dried to give 19-b as an off-white solid (730 mg, yield: 93%). EI-MS (m/z): 210.

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

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); 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. 918321-20-7, name is Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate

A mixture of Xantphos (1.20 g, 2.05 mmol) and tris(dibenzylideneacetone)dipalladium (0) (1.26 g, 1.37 mmol) in anhydrous anisole (76 mL) was stirred under nitrogen, at 50 0C for 30 minutes to provide a an orange- brown solution of the catalyst.[00326] To a stirred mixture of 6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5- carboxylic acid methyl ester (6) (8.00 g, 34.16 mmol) and cesium carbonate (22.48 g, 68.31 mmol) in anhydrous anisole (76 mL) under nitrogen was added 4-bromo-2- chloroiodobenzene (1.60 g, 1.10 equiv., 4.88 mmol). The preformed catalyst, as prepared above, was then added to the mixture to provide a dark brown suspension, which was heated at 100 +/- 2 0C, with stirring at 350 rpm. The reaction was monitored by HPLC analysis. After 41 hours, no 6-amino-7-fluoro-3-methyl-3//-benzoimidazole-5-carboxylic acid methyl ester (6) remained. The reaction mixture was cooled to about 80 0C and IM sulfuric acid (40.99 mL 40.99 mmol) was added. Gas evolution was observed after 10 minutes and the rate of addition was controlled to moderate the effervescence. At the end of the addition the pH was between 7 and 8. Additional sulfuric acid (IM, 10.25 mL, 10.25 mmol) was then added to give mobile slurry with a pH of 0. The mixture was diluted with anisole (20 mL) and Celatom FW- 14 filter agent was added. It was then filtered at about 80 C through a water-wet pad of Celatom FW- 14 filter agent and the cake was washed with anisole (1 x 40 mL + 3 x 20 mL), then water (10 mL). The lower aqueous layer was separated and discarded and the organic layer was washed with 10 % aqueous NaCl solution (2 x 40 mL). This was added to a sodium hydroxide (5.46 g, 68.3 mmol) in methanol (24 mL) and the mixture was heated at 65 C with stirring. After 17.5 hours HPLC analysis indicated that the hydrolysis of the ester was complete and the slurry was cooled to 15 C, then filtered on a sinter. The solid was washed with water (4 x 24 mL), MTBE (24 mL), and acetonitrile (2 x 25 mL) and then dried at 45 0C in a vacuum oven to provide 11.07 g of 6-(4- EPO bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (7) as a fine pale brown solid (assay 93.7% by 1H NMR), actual wt 10.37 g (72.2% yield). 1H NMR (400 MHz, d6 DMSO) delta 3.85 (3H, s, NMe), 6.53 (IH, dd, J 9, 7, Ar-H), 7.27 (IH, dd, J 9S 2.5, Ar-H), 7.56 (IH, d, J 9, Ar-H), 7.97 (IH, s, Ar-H), 8.20 (IH5 s, Ar-H), 11.5 (IH, s, CO2H). 13C NMR (100 MHz, d6 DMSO) delta 31 (CH3), 108 (CH, d, J 2), 109 (CH), 117 (C, d, J6), 122 (C), 124 (C, d, J7), 127 (C)5 130 (C)5 131 (C), 132 (C, d, J9), 133 (C5 d, J l l), 141 (C), 145 (CF, d5 J 252), 146 (CH)5 170 (C=O).

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; ARRAY BIOPHARMA INC.; ASTRAZENECA AB; WO2007/2157; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-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 4857-06-1, Computed Properties of C7H5ClN2

Step3: Under nitrogen protection,Add to the reaction vessel2-chlorobenzimidazole (1.41 g, 9.2 mmol),Phenylboronic acid (1.02 g, 8.4 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL,20mL of ethanol and 20mL of distilled water,Stir at 120 ° C for 3 h.After the reaction is over, the distilled water stops the reaction.Extracted with ethyl acetate,The organic layer was dried over MgSO 4The solvent was removed by distillation under reduced pressure.After purification by silica gel column chromatography, Intermediate 77-3 (1.22 g, 75percent).

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; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (34 pag.)CN108822041; (2018); A;,
Imidazole – Wikipedia,
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 1402838-08-7 as follows. Safety of 2-(1-Trityl-4-imidazolyl)benzaldehyde

Compound 0403-119 (397 mg, 1.39 mmol, 1.9 equiv),Compound 2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (300 mg, 0.72 mmol, 1 eq) andCesium carbonate (468 mg, 1.44 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 1-(benzodioxan-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)benzene. The base) propane-2-en-1-one (413 mg, yield: 99.27%) was a yellow solid.

According to the analysis of related databases, 1402838-08-7, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-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 1003-21-0, Product Details of 1003-21-0

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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

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;,
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. 16042-25-4, name is 2-Imidazolecarboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N2O2

60 g of N,N-dimethylformamide as a solvent and Zn(OAc)2 and benzimidazole in a molar ratio of 1:1.5 were placed in a flask. The reaction was allowed to proceed at 130 C. for 24 h. The resulting solid was collected by filtration. The solid was precipitated in N,N-dimethylformamide, collected, and dried under vacuum at 180 C. for 3 h to afford Zn(benzimidazole)1.6(OAc)0.4 as a zinc-imidazole complex mixed catalyst. The catalyst was analyzed by Fourier-transform infrared (IR) spectroscopy and X-ray diffraction (XRD) and the results are shown in FIGS. 1-3.

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, Hyun Joo; Jae, Jungho; Kim, Hong Gon; Dahnum, Deliana; Cho, Shinhye; (14 pag.)US2020/61596; (2020); A1;,
Imidazole – Wikipedia,
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 71759-89-2 as follows. Application In Synthesis of 5-Iodo-1H-imidazole

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 52099-72-6, 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows.

1-isopropenylbenzimidazolone (0.5 g, 2.9 mmol) in DMA (8 niL) was added and trimethyl-(4- methyl-benzo[&]thiophen-3-ylmethyl)-ammonium; iodide (1.0 g, 2.9 mmol) and K2CO3 (0.80 g, 5.74 mmol). The reaction mixture was heated to 120 0C for 15 min in a microwave and then 150 0C for another 5 min. The mixture was diluted with ethyl acetate and washed with water (x4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2CkMeOH as an eluent to afford 0.7 g of the desired product as a white solid

The chemical industry reduces the impact on the environment during synthesis 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); 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. 615-16-7, name is 2-Hydroxybenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Hydroxybenzimidazole

An ice-cold mixture of sodium hydride (8.00 g, 60% dispersion in mineral oil, 200 mmol) and 145 (8.94g, 66.6 mmol) in DMF (250 mL) under a dry nitrogen atmosphere was allowed to gradually warm to room temperature. To the resulting mixture, iodoethane (16 ml, 200 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was taken up in hexanes and filtered. The resulting brown solid was dried under reduced pressure to give 146 (9.00 g, 71% yield). This material was used without purification. [0394] Step Two: A mixture of DMF (3.6 g, 49 mmol) and POCl3 (9.6 mL, 100 mmol) was stirred at room temperature under a dry nitrogen atmosphere for 1 hour. The flask containing this mixture was then placed in a 45 C. oil bath and 146 (7.6 g, 40 mmol) was added in small portions. The oil bath temperature was raised to 70 C. and the mixture was stirred overnight, then cooled to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a 7:3 mixture of 147:146 (6.69 g). This material was used without purification.

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; Biediger, Ronald J.; Chen, Qi; Decker, E. Radford; Holland, George W.; Kassir, Jamal M.; Li, Wen; Market, Robert V.; Scott, Ian L.; Wu, Chengde; Li, Jian; US2004/63955; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem