Category: imidazoles-derivatives

Electric Literature of 13275-42-8, 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 13275-42-8 as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuCl2 (7 mg, 0.05 mmol, 10 mol%), K3PO4 (212 mg, 1 mmol), 1,10-phenanthroline monohydrate (20 mg, 0.1 mmol, 20 mol%), 2-(2-bromophenyl)-1,4,5,6-tetrahydropyrimidine 1 or 2-(2-bromophenyl)- 1H-benzo[d]imidazole 4 (0.5 mmol), and N-heterocycle 2 (0.5 mmol). The Schlenk tube was evacuated and backfilled with O2 (this procedure was repeated three times). Under a counter flow of O2, DMF (2.0 mL) was added using a syringe. The reaction mixture was stirred at 110 C for 24 h. After the reaction was completed, the mixture was extracted with dichloromethane (3 ¡Á 15 mL), and then the organic layer was washed with brine (3 ¡Á 10 mL) and dried over anhydrous Na2SO4. Subsequently, the solvent was removed, and the product was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol as the eluent, affording the pure products.

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Dingben; Huang, Ling; Yang, Jianguo; Ma, Junna; Zheng, Yingying; Luo, Yi; Shen, Yang; Wu, Jiashou; Feng, Chao; Lv, Xin; Tetrahedron Letters; vol. 59; 21; (2018); p. 2005 – 2009;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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 26576-46-5, Safety of 5-Acetoacetlamino benzimdazolone

This Comparative Example follows the conventional method described in German Patent No. 3140141. 2.0 g (0.0146 mol) of Anthranilic acid, 35 mL of deionized water, and 8.5 mL of 5 M hydrochloric acid are mixed with magnetic stirring while stirring in a 3-neck round bottom flask equipped with a thermometer. The clear solution is cooled to below 0C before adding dropwise a solution of 1.058 g NaNO2 (0.0153 mol) dissolved in 6 mL deionized water (about 2.5M NaNO2) at a rate that maintains an internal temperature below 0C. The diazo solution is kept stirring cold for at least 30 min. A second solution is prepared by mixing 3.47 g (0.0149 mol) of 5-acetoacetylamino-benzimidazolone (TCI America), with a basic solution containing 1.715 g (0.0429 mol) of NaOH dissolved in 10 mL deionized water. This second solution is then added to a third mixture containing 195 mL deionized water, 6 mL of glacial acetic acid (0.105 mol), and sodium hydroxide (2.29 g, 0.0573 mol), resulting in a finely suspended colloidal solution of white coupling component. The cold diazo solution is then added dropwise at room temperature to a vigorously stirred suspension of the coupling component, producing a yellow pigment slurry. The yellow mixture is stirred for at least 6 hours to complete the color development, after which time the slurry is filtered under vacuum through Versapor 0.8 mum filter membrane (PALL Corp.). The pigment wetcake is reslurried into 200 mL deionized water and then is vacuum filtered twice more, after which time the pigment wetcake is freeze-dried for 48 hours. The final product is a dark yellow powder (4.96 g, 89% yield), and after analysis by TEM imaging, consists of large aggregates and agglomerates of elongated rod-shaped particles having average lengths ranging from about 200 to about 500 nm.

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; Xerox Corporation; National Research Council of Canada; EP2290012; (2011); A2;,
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 6232-91-3 as follows. SDS of cas: 6232-91-3

2-Amino-5-methoxy-1H-benzimidazole was obtained from 4-methoxybenzene-1,2-diamine following the reported operation. 17 To a solution of N-carbobenzyloxy-l-proline (2.49 g, 10.0 mmol, 1.0 equiv) and 2-amino-5-methoxy-1H-benzo[d]imidazole (1.79 g, 11.0 mmol, 1.1 equiv) in CH2Cl2 (30.0 mL) N,N’-dicyclo-hexylcarbodiimide (2.26 g, 11.0 mmol, 1.1 equiv) and 4-dimethylamino pyridine (1.34 g, 11.0 mmol, 1.1 equiv) were added at 0 ¡ãC under N2 atmosphere. The reaction mixture was stirred for 30 min at 0 ¡ãC, then at room temperature for 24 h. The reaction mixture was filtrated through silica gel pad (SiO2 15 g) to remove dicyclohexylurea. Further purification was through flash column chromatography (Methanol/DCM=1:10). 1H NMR (400 MHz, CHCl3-d): delta 7.50-7.30 (4H, m), 7.20-6.80 (4H, m), 5.15-5.05 (2H, m), 4.60-4.40 (1H, m), 3.84 (3H, d, J=7.80 Hz), 3.72-3.48 (2H, m), 2.38-2.20 (1H, m), 2.10-1.75 (3H, m). 13C NMR (400 MHz, CHCl3-d): delta 179.3, 156.6, 154.5, 146.6, 136.7, 128.3, 128.0, 127.7, 127.4, 111.9, 66.5, 59.4, 55.7, 46.8, 30.8, 23.3. HRMS (ESI): m/z [M+H+] calcd for C21H23N4O4 395.1719, found 395.1714.

According to the analysis of related databases, 6232-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tang, Gongkun; Guen, Uemit; Altenbach, Hans-Josef; Tetrahedron; vol. 68; 49; (2012); p. 10230 – 10235,6;; ; Article; Tang, Gongkun; Guen, Uemit; Altenbach, Hans-Josef; Tetrahedron; vol. 68; 49; (2012); p. 10230 – 10235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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. category: imidazoles-derivatives

A slurry of tert-butyl 2?-oxospiro[8-azabicyclo[3 .2.1 ]octane-3, I ?-cyclobutanej-8-carhoxylate (2.65 g, 9.98 .mmol), 2-[ 1.-(triphenylmethyl)- IH-imidazol-4-yl.]benzaldehyde (4.55 g,11.0 mmol) and Ca(OH)2 (1.48 g, 20.0 mmol) in EtOH (33 mL) was stirred for 24 h at 80 C.The reaction was cooled to room temperature and insoluble material was removed by filtration. The filtrate was concentrated. The residue was purified by a silica gel column eluting withDCM/methanoj. (90:10) to afford 5.60 g (85%) tertbutyl E)-2?-oxo-3?(2-(1-trity1-1Wirnidazo1.-4-yl)benzylidene)-8-azaspiro[bicyclo{3 .2.1 ]octane-3, 1 ?-cyclobutane]-S-carboxylate as a pale yellow solid. LCM.S (ESI) m/z 662.3 [M+F1]4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1402838-08-7, its application will become more common.

Reference:
Patent; GENENTECH, INC.; PEI, Zhonghua; PASTOR, Richard; GAZZARD, Lewis; PARR, Brendan; LIU, Wendy; MENDONCA, Rohan; WU, Guosheng; YUEN, Po-Wai; (183 pag.)WO2019/5559; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 53484-17-6, 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. 53484-17-6 name is 1-Methyl-1H-benzo[d]imidazole-5-carboxylic acid, 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 stirred solution acid compound 172 (6.7 g, 38.06 mmol) and N,O- dimethylhydroxylamine (5.57 g, 57.09 mmol) in DCM (70 mL) at 0 oC was added DIPEA (13.53 mL, 76.13 mmol), stirred for 15 min, followed by addition of HATU (21.69 g, 57.09 mmol), again stirred for 15 min. The reaction mixture was then stirred at room temperature for overnight. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ice cold water and extracted with DCM. The combined organic layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford a crude compound. The crude compound was purified by silica gel column chromatography using 2% MeOH/DCM to afford the title compound 173 (8.1 g, 98.78%) as a brown liquid. TLC: 5% MeOH/DCM (Rf: 0.3). 1H LCMS Calculated for C11H13N3O2: 219.10; LCMS observed: 219.95 (M+1)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-benzo[d]imidazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (2018); 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 40197-20-4 as follows. Application In Synthesis of 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid

Preparation Example 1 N-[3-(dimethylamino)propyl]-N’-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg), and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring at room temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure. The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. The mixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collected by filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

According to the analysis of related databases, 40197-20-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; (31 pag.)EP3231426; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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 939-70-8

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-70-8, its application will become more common.

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

Reference of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under nitrogen, imidazole was dissolved in anhydrous THF, and an appropriate amount of acetic anhydride was dropped slowly into the solution; then reaction was carried out for about half an hour accompanied by exothermic phenomena. After the reaction was completed, the solvent was removed by vacuum reduced pressure concentration to generate a solid product. Then, the obtained solid was rinsed with n-hexane and filtered to provide compound 11 as white solid, with yield of about 98percent.

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

Reference:
Patent; Eternal Chemical Co., Ltd.; Cheng, Pi-Jen; Chou, Meng-Yen; Lee, Chuan Zong; Wu, Chung-Jen; US2013/172569; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of Na2MoO4*2H2O (0.0718 g, 0.296 mmol), 2,2′-biimidazole (biim, 0.0430 g, 0.257 mmol), NiF2*4H2O (0.0095 g, 0.056 mmol), and Na2SiO3*9H2O (0.0708 g, 0.249 mmol) in H2O (10 mL) was adjusted to pH 2.5 with HCl (1.0 mol/L solution in water) and heated at 150 C for 48 h in a sealed 25 mL teflon-lined stainless vessels under autogenous pressure. After cooling to ambient temperature with 800 min, black block crystals (yield50%, based on Na2MoO4*2H2O) were obtained.

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, 1H,1’H-2,2′-Biimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Hao; Chen, Yi-Ping; You, Zhu-Chai; Zhou, Meng-Xi; Zhang, Ning; Sun, Yan-Qiong; Chinese Chemical Letters; vol. 26; 2; (2015); p. 187 – 192;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N4O2

EXAMPLE 8; PREPARATIONOFA LINEAR CUCURBITURIL TRIMER; In another exemplary pathway for preparing a linear cucurbituril trimer, disubstituted cucurbiturils are prepared and are thereafter attached to an assembling unit, as is presented in Figure 24. As an exemplary starting material, a”benzil trimer” (Figure 24, Compound 39) is reacted with urea in a 1: 6 ratio, in benzene and trifluoroacetic acid, so as to afford a benzil-derived structure having three glycoluril units attached thereto. The latter is further substituted at each end with a carboxyl group, which can be used for further attachment of a variety of functional moieties or for forming cucurbituril assemblies. Thus, the benzil-derived glycoluril structure is reacted with glycoluril, Compound 2, in a 1: 15 ratio, and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form a linear, derivatized, cucurbituril trimer (Figure 24, Compound 40)

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; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem