Month: July 2021

Reference of 870837-70-0, 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. 870837-70-0 name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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 synthesis of curcumin analogues 25-34 from corresponding benzaldehyde precursors was carried out by modified literature methods (Scheme 5). The appropriate vanillin derivative (1 equiv) and boric anhydride (0.6 equiv), dissolved in anhydrous DMF in a flask which was thoroughly flushed with nitrogen before use, were stirred at room temperature. Under nitrogen, 2,4-pentanedione (0.6 equiv) and 2,2-dimethoxypropane (1 equiv) or tributyl borate (2 equiv) were added dropwise. The mixture was stirred and heated to a temperature of 70 C under nitrogen. About 30 min later, n-butylamine (0.2 equiv) was added dropwise slowly under nitrogen, and the mixture was allowed to stir at 70 C for 2-4 h. At the end of the reaction, the mixture was hydrolyzed by adding hot (70 C) aqueous 5% acetic acid and stirred until it cooled down. The mother liquor was extracted three times with EtOAc, and the combined organic layers were washed three times, dried over anhydrous Na2SO4, and filtered. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Qin; Zhong, Ying; Yan, Lin-Na; Sun, Xun; Gong, Tao; Zhang, Zhi-Rong; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1010 – 1014;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 11c (lg, 4.6 mmol) in THF (40 mL) was added CDI (2.1 mol eq, 1.4 g) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×30 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (red oil, 1.36 g, 98% yield). The oil obtained (1.36g, 3.99 mmol) was dissolved in DMF (20 mL) and the bicyclic amine la was added (0.8 mol eq, 0.47g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (100% EtOAc) to obtain the product as a white solid (0.29g, 21% Yield). 1HNM (DMSO, 200 MHz) delta 1.26 (s, 9H), 4.35 (d, 2H, J=6), 6.64 (d, 1H, J=8), 6.87 (m, 3H), 7.40 (m, 3H), 8.31 (s, 1H), 9.94 (bs, 1H), 10.59 (bs, 1H). [M+1] 373.05 (C19H21ClN4O2 requires 372.85)

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

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1792-40-1,Some common heterocyclic compound, 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, molecular formula is C8H7N3O2, 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.

In 100mL round bottom flask, 2-methyl-5-nitrobenzimidazole (0. 46g, 0. 0027mol), potassium carbonate (0. 75g, 0. 0054mol) and the amount of acetonitrile, temperature control The reaction was stirred 50 C 0. 5h, cooled to room temperature, II-1 (1. 00g, 0. 0027mol) was heated to 80 C and stirring continued, until thin layer chromatography the reaction was completed track, and then by concentration, extraction, column chromatographic separation, recrystallization, and dried to give square 0. 31g Compound 1-29, yield 32.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-5-nitro-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Southwest University; Zhou, Chenghe; Zhang, Ling; (39 pag.)CN104086534; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 10111-08-7, These common heterocyclic compound, 10111-08-7, name is Imidazole-2-carboxaldehyde, 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.

Sodium carbonate (1.10 g, 10.4 mmol) was added to a solution of hydroxylamine hydrochloride (1.44 g, 20.7 mmol) in water (5 ml) and adjusted to pH 7. Imidazole-2-carboxaldehyde (1,1.00 g, 10.4 mmol) was added potionwise to resulting reaction mixture. After being stirred for 1 h at 70 C, the product was filtered, washed with cold water and dried in vacuo to give a white solid (0.83 g, 72%).

Statistics shows that Imidazole-2-carboxaldehyde is playing an increasingly important role. we look forward to future research findings about 10111-08-7.

Reference:
Article; Kim, Tae Keun; Lee, Byung Woo; Lee, Hai Whang; Chung, Kyoo-Hyun; Kim, Jin Seuk; Bulletin of the Korean Chemical Society; vol. 34; 6; (2013); p. 1864 – 1866;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3543-74-6, name is Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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 3543-74-6, Product Details of 3543-74-6

Example-2 Preparation of Ethyl 4-{5-[bis(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (IV) 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III, 90.0 g, 1.15 mole) was added to dichloromethane (6.24 L) and agitated till clear solution is formed. A solution of thionyl chloride (292.3 g, 2.52 mol) in dichloromethane (1.56 L) was added slowly in 2 to 3 hours. After complete addition of thionyl chloride solution, reaction mixture was refluxed at 35-45 C. for 6 hours. The reaction mixture was cooled to 20-30 C. and 1.95 L dichloromethane was added. Potassium carbonate solution (351.0 g in 1.95 L water) was added to the reaction mixture slowly to control the evaluation of effervescence. The layers were separated. The organic (dichloromethane) layer was washed with brine solution. The organic layer was concentrated at 30-35 C. under vacuum till viscous mass is obtained. The viscous mass was dissolved in acetone (1.95 L) and DM water (1.365 L) was slowly. The resulting mixture was stirred at 20-30 C. for one hour followed by cooling to 0-5 C. The solid separated out was washed with chilled mixture of acetone (390 mL) and DM water (195.5 mL) twice. The material was sucked dried to dryness and used as such for next step.

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, Ethyl 4-(5-(bis(2-hydroxyethyl)amino)-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); 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. 79917-88-7, name is 1,3-Dimethyl-1H-imidazol-3-ium chloride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H9ClN2

Take a 100 mL three-necked flask,1,3-dimethylimidazole was added thereto successively under nitrogen protection(1.33 g0 · 01 mol), acetone (100 mL, 1.71 mol) and then 30percent methanol sodium methoxide solution (1.8 g, 0.01 mol) was added to control the reaction temperature at 15 ° C. After 4 h of reaction, the reaction solution was filtered and the filtrate was charged into a 250 mL autoclave.

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 79917-88-7.

Reference:
Patent; Guangdong Laifoshi Pharmaceutical Co., Ltd.; Zhou Zhangtao; Xu Junye; Fei Anjie; Tan Chuanwen; Huang Zhining; Xiao Shihua; Yan Yannan; (5 pag.)CN106892807; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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