Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 670-96-2, name is 2-Phenyl-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 670-96-2, COA of Formula: C9H8N2

General procedure: A mixture of Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand II (21.6 mg, 0.020 mmol), and F-PEG (0.25 g, 0.10 mmol) in MeOH (1 mL) was heated to dissolve all the reagents added completely and MeOH was removed under the reduced pressure. H2O (6 mL) was added to the residue and then 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol) and imidazole (2a, 13.6 mg, 0.20 mmol) were added. The whole reaction mixture was stirred under an O2 atmosphere at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL×3). The organic layer was washed with H2O (10 mL×3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (26.4 mg, 78%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Phenyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Inamoto, Kiyofumi; Nozawa, Kanako; Kadokawa, Jun; Kondo, Yoshinori; Tetrahedron; vol. 68; 38; (2012); p. 7794 – 7798;,
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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 288-32-4

To a mixture of toluene and imidazole was added triethyl amine followed by chloroacetonitrile.The reaction mixture was heated and maintained for 7 to 8 hrs. The reaction mass was cooledand the toluene layer was separated. To the reaction mass methylene dichloride was added, stined and filtered. The filtrate was distilled under vacuum. To the residue tetrahydrofuran was added and the reaction mixture is further distilled to obtain the title product. The product thus obtained was recrystallized in isopropyl alcohol. HPLC purity> 99.0 % Chiral purity>99.0%

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; BHUSHAN, Kumar Hari; ZHOPE, Sunil Sudhakar; GHADIGAONKAR, Shailesh Govind; SINGH, Pardeep; DESHMUKH, Shekhar Ashok; CHAND, Prem; (35 pag.)WO2016/92478; (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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-1-methyl-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

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:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 52099-72-6, The chemical industry reduces the impact on the environment during synthesis 52099-72-6, name is 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.

To a stirred solution of l-Isopropenyl-l,3-dihydro-benzimidazol-2-one (5g, 28.7mmol) in DMF (20ml) was added methyl acrylate (2.8ml, 31.6mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt% in MeOH, 3.2ml). The resulting solution was stirred at ambient temperature until the reaction was complete. After this time the reaction was poured into water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic layers were dried (MgSCH), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 30% ethyl acetate/hexanes). The product-containing fractions were combined and concentrated to give 4.8g (64%) of the desired product.

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, 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 760212-58-6, 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate I-3 4.23 g (11.0 mmol), Intermediate I-4 3.49 g (10.0 mmol), Pd (PPh3) 4 0.06 g (0.5 mmol) and K2CO34.15 g (30.0 mmol) of THF/H2O (2/1 volume ratio) mixed solution and then dissolved in 40 mL, was stirred at 80 for 5 hours. after cooling to room temperature the reaction solution was added to 40 mL water and extracted three times with diethyl ether, 50 mL. The combined organic layers were dried over magnesium sulfate, and separation of the residue obtained by evaporation of the solvent by silica jelgwan chromatography to give the compound 4 4.33 g (yield 81%). The resulting compound was confirmed by LC-MS and 1H NMR.

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Young Kuk; Kim, Kwang Hyun; Lee, Uhn Young; (77 pag.)KR2015/39485; (2015); 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

c) 1.00 g (2.68 mmol) 6-bromo-2-iodo-dibenzofuran, 1.75 g (5.36 mmol) caesium carbonate, 130 mg (0.67 mmol) copper(l) iodide and 150 mg (1.34 mmol) L-proline are added to 670 mg (3.22 mmol) 5H-benzimidazo[1 ,2-a]benzimidazole in 20 ml DMSO under nitrogen. The reaction mixture is stirred for 18 h at 100 C and filtered. THF and toluene are added to the organic phase and the organic phase is washed with water. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product can be used without further purification in step d) (yield = 650 mg (78 %)).1H NMR (400 MHz, CDCI3): delta 8.66 (d, J = 2.2 Hz, 1 H), 8.13-8.19 (m, 2H), 7.96-8.07 (m, 3H), 7.66-7.78 (m, 3H), 7.25-7.45 (m, 5H).

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 28890-99-5.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic 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 22884-10-2, COA of Formula: C5H6N2O2

A suspension of imidazol-1-ylacetic acid, compound of formula 2 (50g, 0. 396mol) and phosphorous acid (48.7g, 0. 594mol) in sulfolan (180ml) was heated to 75 C for 30 min. The mixture was cooled to 35-40 C and phosphorous trichloride (117ml, 1. 346mol) was gradually introduced while maintaining the temperature between 35-45 C. The mixture was heated to 63-67 C for 3 hours, whereby white solid results. It was then cooled to 0- 5’C and quenched by slow addition of water (500ml) at 0-5 C over a period of 1 hour. The resulting clear solution was heated at 100 C for 3 hours, cooled to ambient temperature and charcoalized. Acetone was added to the charcoalized solution. The mixture was then stirred for 4 hours at 20-25 C and the crystallized product was filtered, washed sequentially with chilled water, acetone and dried to obtain zoledronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Imidazol-1-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2005/66188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 614-97-1, A common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16093-82-6, A common heterocyclic compound, 16093-82-6, name is 1H-Imidazole-2-carboxamide, molecular formula is C4H5N3O, 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.

A solution of lH-imidazole-2-carboxylic acid amide (360 mg, 3.24 mmol) and phenyl dichlorophosphate (2 mL) was heated at 1700C for 8 min, in a microwaves oven. The reaction mixture was cooled at room temperature and poured into water (50 mL). The solution was cooled at 0C and the pH was adjusted to 11 by addition of NaOH 10 M. Ethyl acetate was added and the phases were separated. The organic layer was dried over sodium sulphate and evaporated in vacuo to provide IH- Imidazole-2-carbonitrile. A solution of lH-imidazole-2-carbonitrile and hydroxylamine (50% sol. in water, 794 muL, 13 mmol) in ethanol (15 mL) was refluxed for 4h. The solvent was removed and the crude N-hydroxy-lH-imidazole-2- carboxamidine was used for the next step without further purification. EPO Yield: quantitative; LCMS (RT): 0.62 min (Method D); MS (ES+) gave m/z: 127.0 (MH+).

The synthetic route of 16093-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADDEX PHARMACEUTICALS SA; WO2006/123257; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem