Author: Jessica.F

Electric Literature of 23785-21-9,Some common heterocyclic compound, 23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate, molecular formula is C6H8N2O2, 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.

Preparation of intermediate II-30; LiHMDS was added to a -10C solution of ethyl imidazole-4-carboxylate in DMF. After 15 min, o-diphenylphosphinylhydroxylamine (CAS: 72804-96-7) was added in one portion and the mixture was stirred at rt for 6 h. The reaction was quenched with water (an exothermic reaction occcurs) until a clear solution is obtained. The solvents were removed under reduced pressure. The residue was dissolved in water and it was extracted with DCM (x3). Combined organic layers were dried and evaporated. The residue was purified on silica gel (biotage, DCM/MeOH 0 to 10% MeOH) to obtain: 356 mg of desired product, intermediate II-30. Yield 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-imidazole-4-carboxylate, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2849-93-6,Some common heterocyclic compound, 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, molecular formula is C8H6N2O2, 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: A suspension of the appropriate acid 17d-e (1 eq, 12.7 mmol) in EtOH (21 ml) was treated dropwise with SOCl2 (3 eq) under ice cooling, then heated to reflux over night. The solution was then concentrated in vacuum, treated with EtOH (3×20 mL) and n-hexane (3×20 mL)and dried under vacuum to give the pure title compound.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 56 – 68;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2466-76-4,Some common heterocyclic compound, 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, molecular formula is C5H6N2O, 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: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

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

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2302-25-2, name is 4-Bromo-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. SDS of cas: 2302-25-2

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The synthetic route of 4-Bromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-22-5, 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. 934-22-5, name is 6-Aminobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2·2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 × 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3×10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

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

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 1H-Imidazole-4,5-dicarboxylic acid

General procedure: All complexes were prepared by a similar procedure. A mixture of Ln(NO3)3 [Ln=Eu3+ (1), Tb3+ (2), Er3+ (3), Nd3+ (4)] (0.10mmol), H3IDC (0.12mmol), 4,4-bipy (0.10mmol), DMF (2mL), and H2O (15mL) was adjusted to pH=3 with acetic acid and then placed in a sealed Teflon-lined stainless steel vessel (25mL), which was heated at 160C for 3d. Then the reaction system was cooled to room temperature over 2d at a rate of 5C/h to give block crystals of 1-4, respectively.

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; Jin, Jun-Cheng; Tong, Wen-Quan; Fu, Ai-Yun; Xie, Cheng-Gen; Chang, Wen-Gui; Wu, Ju; Xu, Guang-Nian; Zhang, Ya-Nan; Li, Jun; Li, Yong; Yang, Peng-Qi; Journal of Solid State Chemistry; vol. 225; (2015); p. 216 – 221;,
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. 3034-42-2, name is 1-Methyl-5-nitroimidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5N3O2

General procedure: To a solution of 1-methyl-5-nitro-1H-imidazole (10 g, 0.078 mol) in EtOH (400 mL) was added wet10% Pd/C (2 g), and the mixture was stirred at room temperature for 1 hr. Then diethyl 2- (ethoxymethylene)malonate (20 g, 0.094 mol) was added. The mixture was stirred under H2 for overnight. Pd/C was removed after filtration and the solvent was evaporated in vacuum. The residue was purified by flash column (DCM/MeOH = 10/1) to give diethyl 2-(((1-methyl-1H-imidazol-5-yl)amino)methylene)malonate (6 g, yield: 28.7%) as brown oil. MS: m/z 268.1 (M+H).

According to the analysis of related databases, 3034-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4ClF3N2

17. 5-Trifluoromethyl-2-[(4-methoxy-2-pyridylmethyl)thio]-(1H)-benzimidazole 22.1 g (0.1 mole) of 5-trifluoromethyl-2-chlorobenzimidazole and 15.7 g (0.11 mole) of 4-methoxy-2-thiomethylpyridine in 250 ml of isopropanol are heated under reflux for 10 hours. The solvent is stripped off in vacuo, and 500 ml of ice water are added to the residue. The title compound is filtered off with suction and recrystallized from acetonitrile. M.p. 180-182 C.

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4472409; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-22-5, 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. 934-22-5 name is 6-Aminobenzimidazole, 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: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of (1H-Imidazol-1-yl)(phenyl)methanone

General procedure: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.

The synthetic route of 10364-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik; Tetrahedron Letters; vol. 53; 19; (2012); p. 2373 – 2376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem