Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic 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 641571-13-3, Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid

(E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amine (100 mg, 0.354 mmol) and 3-(4-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)benzoic acid (96 mg, 0.354 mmol) were dissolved in DMF (1.5 mL), HATU (404 mg, 1.063 mmol) and TEA (0.248 mL, 1.7728 mmol) were added thereto and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The resulting mixture was purified by silica gel chromatography to obtain the title compound (142 mg, 75% yield). MS m/z [M+1] 535.15.

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; HANMI SCIENCE CO., LTD.; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; Son, Jung Beom; Jung, Seung Hyun; Choi, Wha ll; Jung, Young Hee; Choi, Jae Yul; Song, Ji Yeon; Lee, Kyu Hang; Lee, Jae Chul; Kim, Eun Young; Ahn, Young Gil; Kim, Maeng Sup; Choi, Hwan Geun; Sim, Tae Bo; Ham, Young Jin; Park, Dong-sik; Kim, Hwan; Kim, Dong-Wook; US2013/53370; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15813-09-9, These common heterocyclic compound, 15813-09-9, name is 4,5-Diiodo-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.

To a solution of 4,5-diiodo-1H-imidazole (2.0 g, 5.9 mmol) in DMF (45 mL) was added NaH (60% in mineral oil, 356 mg, 8.91 mmol). The mixture was stirred at RT for 30 min, then treated with 2-(2-bromoethyl)isoindoline-1,3-dione (2.33 g, 8.91 mmol). The mixture was stirred at 60 C. overnight, then allowed to cool to RT and poured into water (30 mL). The precipitated solid was collected and dried to give the title compound as a white solid (1.72 g, 59%). MS (ES+): C13H9I2N3O2 requires: 493, found: 434 [M+H]+.

The synthetic route of 15813-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); A1;,
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. 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H7N3O

EXAMPLE 3 1-(6-Chloropyrazin-2-yl)-1H-benzimidazole-5-carboxamide and and A mixture of 2, 6-dichloropyraz’rne (2.0 g, 13. 4 mmol), 1H-benzimidazole-5-carboxamide (2. 0 g, 12.3 mmol) and cesium carbonate (5. 6, 17. 2 mmol) in DMF (10 mL) was heated at 90C for 3h. The solution was cooled to RT and diluted with ethyl acetate (20 mL) and filtered. The solid material was washed with chloroform-methanol (20mL, 4:1) and the combined flitrates (at) concentrated in vacuo. The residue thus obtained (3. 02 g) was used without further purification. m/z (EI) 273/275 (M+1)

According to the analysis of related databases, 116568-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2301-25-9, 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 2301-25-9 as follows.

YB112 (162mg) was dissolved in THF solvent. After the reaction system was deaerated,10% Pd / C 20mg was added.A hydrogen balloon was added to the reaction system, and the reaction was allowed to proceed overnight.The reaction was filtered and washed with ethyl acetate, concentrated, and the target product YB126 (154 mg) was purified on a silica gel column.

According to the analysis of related databases, 2301-25-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5805-57-2, 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. 5805-57-2 name is (1H-Benzo[d]imidazol-2-yl)methanamine, 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.

General procedure: The 4-chloro-6-methylpyrimidin-2-amine (1) (1 mmol)was dissolved in dry ethanol (5 ml). To this, (benzoxazol-2-yl)methanamine (3a)/(benzothiazol-2-yl)methanamine (3b)/(1H-benzimidazol-2-yl)methanamine (3c) (1.1 mmol) and acatalytic amount of methanesulfonic acid (0.2 ml) wereadded and refluxed for 4-6 h. After completion of thereaction, the reaction mixture was cooled and diluted withwater (15 ml). The separated solid was filtered, washed withwater, dried and recrystallized from 2-propanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzo[d]imidazol-2-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Seenaiah, Dandu; Rekha, Tamatam; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 2; (2017); p. 431 – 441;,
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. 1122-28-7, name is 4,5-Dicyanoimidazole, A new synthetic method of this compound is introduced below., Safety of 4,5-Dicyanoimidazole

Example 19 2-Bromo-4,5-dicyanoimidazole (21) STR70 To 1.18 g (10 mmol) 4,5-dicyanoimidazole and 25 ml 0.1 M NaOH was added 1.8 ml Br2 (35 mmol). The mixture was stirred overnight at room temperature and then acidified with dilute HCl. The solid was filtered, rinsed with water and recrystallized from water to give 1.5 g of dicyanobromoimidazole 21 (yield 76.4%).: m.p. 147-149 C. (lit. 141-143 C.); Rf=0.65 (ethyl acetate_methanol=4:1); MS(EI): 198([M+2], 96%), 196 ([M+ ], 100%), 171 (28.5), 169 (29.2), 117 (27.4), 91 (19.0), 64 (20.6), 53 (22.4), 38 (18.8).

The synthetic route of 1122-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Isis Pharmaceuticals, Inc.; McGill University; US6160109; (2000); A;,
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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,4-Dimethylimidazole

A solution of methyl mesylate (25.4 mL, 300 mmol) in acetone (50 mL) was added dropwise to a stirred mixture of 2,4-dimethylimidazole (25.00 g, 260 mmol), potassium carbonate (55.20 g, 400 mmol) and acetone (500 mL). Stirring under argon was then continued at room temperature for 16 hours. The resulting solid was filtered off, and the solvent was removed under reduced pressure. The residue was triturated with THF (200 mL) to give crystalline product (59-3) (14.47 g, 25% yield).The filtrate was treated with activated charcoal, filtered through a layer of Celite, and the solvent was removed under reduced pressure. Upon storage of the residue at room temperature, some crystalswere formed, and these crystals were separated, washed with THF and dried in a vacuum oven to give1,2,4-trimethylimidazole (59-1) (4.01 g, 14% yield). Concentration of the filtrate gave a mixture of isomeric imidazoles (59-1) and (59-2) (12.19 g, 43% 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 930-62-1.

Reference:
Patent; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; (0 pag.)WO2018/161025; (2018); 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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H7BrN2

The reactor was charged with palladium(II) acetate (0.160 g, 0.71 1 mmol), 2,8,9-triisobutyl- 2,5,8,9-tetraaza-l-phosphabicyclo[3.3.3]undecane (0.507 mL, 1.421 mmol), and 5-bromo-2- methyl- lH-benzo[d]imidazole (1.5 g, 7.1 1 mmol). The vessel was evacuated and refilled with N2 for 3 cycles and degassed dioxane (14.21 mL) was added, followed by NaHMDS (28.4 mL, 28.4 mmol). The reaction was stirred at 25C for 20 min before 2-(3-fluorophenyl)acetonitrile (73.3 mg, 0.543 mmol) was added. The reaction was then capped and heated at 100C for 3 h. More NaHMDS (6 mL) was added and the reaction was stirred for another 1 h; More NaHMDS (4 mL) was added and the reaction was stirred for another 1 h before it was cooled to room temperature, and quenched with water. The aqueous layer was extracted with EtOAc (3x), washed with brine, dried over MgS04, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by chromatography on silica gel (eluent: 0-100% A in B. A: 10% MeOH in DCM; B: DCM.). LCMS calc. = 266.10, found = 266.04 (M+H)+.

The synthetic route of 1964-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0, SDS of cas: 60-56-0

General procedure: To a slurry of the substituted imidazole-2-thione or pyrimidine-2-thiol (1.0 mmol) and sodium methoxide (2.2 mmol) in methanol (20 mL) was added a solution of substituted 2-(chloromethyl)-pyridine (1.0 mmol) in methanol (10 mL). After the mixture was refluxed with stirring for 4-6 h, the solvent was removed in vacuo and the residue was washed with water to remove the salt, and then extracted with dichloromethane (3 9 10 mL) at room temperature. The solid product was directly obtained by the removal of solvent and further dried at 45 C overnight. The purity of the product was tested by HPLC and characterization of the product was confirmed by IR, 1H NMR, and mass spectroscopies. Data 3-Methyl-[4-(2,2,2-Trifluoroethoxy)-2-Pyridinyl]-Methylthio-1-Methyl-Imidazole (3a) White solid. Yield: 84.5 %. IR (cm-1): 832.7 (-CH2-S-). 1H NMR (CDCl3) delta (ppm): 2.18 (s, 3H, -CH3 in py), 3.23 (s, 3H, -CH3 in imidazole), 4.42 (q, J = 6.0 Hz, 2H,-OCH2CF3), 4.56 (s, 2H, -CH2S-), 6.62 (d, J = 5.6 Hz,1H, H in py), 6.81 (s, 1H, H in imidazole), 6.92 (s, 1H,H in imidazole), 8.30 (d, J = 5.6 Hz, 1H, H in py). MS (EI): m/z calcd. C13H14N3OF3S (M+) 317.3311, found 317.3336.

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:
Article; Ma, Sen; Jia, Ai-Quan; Fan, Fang-Fang; Shi, Hua-Tian; Zhang, Qian-Feng; Journal of Chemical Crystallography; vol. 46; 3; (2016); p. 137 – 143;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: To a stirred suspension of potassium carbonate (0.166 g, 1.2mmol) in ethanol (8 mL) was added 1H-imidazole (0.068 g,1 mmol). The mixture was stirred at 60 C for 1 h and thencooled to room temperature. Compound 3 (0.232 g, 1 mmol)was added and stirred under 70 C. After the reaction wascompleted (monitored by TLC, chloroform/methanol, 30:1,V/V), the solvent was evaporated and the residue was treatedwith water (15 mL) and extracted with chloroform (315mL). The combined organic phase was dried over anhydroussodium sulfate and concentrated under the reduced pressure.The crude product was purified by silica gel column chromatography(eluent, chloroform/methanol, 50:1-30:1, V/V)to afford the pure compound 4a (0.142 g) as white solid

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Peng, Xin-Mei; Kumar, Kannekanti Vijaya; Damu, Guri L.V.; Zhou, Cheng-He; Science China Chemistry; vol. 59; 7; (2016); p. 878 – 894;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem