Category: imidazoles-derivatives

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 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 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

Related Products of 7757-21-3, These common heterocyclic compound, 7757-21-3, name is (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, 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 single neck flask equipped with a condenser and under nitrogen atmosphere was charged 2-CHLORO-3-NITROPYRIDINE (25g, 0. 158 MOLE), Aminomethylbenzimidazole hydrochloride (36. 5g, 0.166 mole) and 200 ml of Ethanol. To this slurry was charged diisopropylethyl amine (137 ml, 0.790 mole) and heated to 65 degrees celcius for 1 hour. Tlc in 5% methanol/ Methylene Chloride (product Rf; 0.5). The reaction was concentrated under vacuo to 100 ml and then cool in an ice bath. Filtered solid and washed cake with minimal amount of Methyl ethyl Ketone to give (LH-BENZOIMIDAZOL-2-YLMETHYL)- (3-NITRO-PYRIDIN-2-YL)-AMINE, a canary Yellow solid (wt= 15.76 g)

Statistics shows that (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 7757-21-3.

Reference:
Patent; TRIMERIS, INC.; WO2004/43913; (2004); A2;,
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. COA of Formula: C29H22N2O

2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (287 mg, 0.693 mmol, 1 eq),Compound (2-(6-fluoro-2-phenylbenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-80) (300 mg, 0.83 mmol, 1.2 equiv) andCesium carbonate (450 mg, 1.386 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product 1-(6-fluoro-2-phenylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one (250 mg, crude) is a yellow solid

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; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8N2

General procedure: To a stirred solution of copper(I) acetate (2.4 mg, 0.020 mmol, 0.10 equiv.), benzimidazole 1a (23.6 mg, 0.20 mmol), and TMP iodonium(III) salt 2a (124.8 mg, 0.24 mmol, 1.2 equiv) in toluene (2 mL), triethylamine (56 mL, 0.4 mmol, 2 equiv) was added under a nitrogen atmosphere. The mixture was stirred for 5 min at room temperature, and the resulting solution was then heated to 50 C for 6 h (the reaction progress was monitored by TLC). After cooling to room temperature, the reaction was quenched by adding 5% aqueous ammonia solution (4 mL). The aqueous layer was extracted thrice with 20 mL of dichloromethane and the combined organic extracts were dried with anhydrous sodium sulfate. The organic solvents were then evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1) to obtain pure N-phenyl benzimidazole 3aa (38.5 mg, 0.198 mmol) in 99% yield

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; Koseki, Daichi; Aoto, Erika; Shoji, Toshitaka; Watanabe, Kazuma; In, Yasuko; Kita, Yasuyuki; Dohi, Toshifumi; Tetrahedron Letters; vol. 60; 18; (2019); p. 1281 – 1286;,
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 3287-79-4 as follows. Computed Properties of C9H10N2S

Example 20 Preparation of Compound No. 952 To 5,6-dimethylbenzimidazole-2-thiol (713 mg, 4 mmol) in dimethylformamide (10 ml), triethylamine (836 mul, 6 mmol) and 2-bromomethylbenzonitrile (1176 mg, 6 mmol) were added. After stirring at 80 C. overnight, water was added to the mixture, followed by extraction with ethyl acetate. After the ethyl acetate phase was dried with anhydrous sodium sulfate, it was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile (1159 mg, yield 99%).

According to the analysis of related databases, 3287-79-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEIJIN LIMITED; US2005/267148; (2005); 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., Computed Properties of C5H7BrN2

A solution of 5-bromo-1,2-dimethyl- 1H-imidazole (10.6 g, 60.8 mmol) in THF (400 mE) was cooled to -77 C. Maintaining a temperature of<-70 C., nBuLi (27.7 ml, 72.0 mmol, 2.5 M in hexanes) was added over 10 mm. After 10 mm, a solution of (4-chloro-2-methoxy-3-(4-(trifluorom- ethyl)benzyl)quinolin-6-yl)(1 -methyl-i H-i ,2,3-triazol-5-yl)methanone (20.0 g, 43.4 mmol, Intermediate 63) inTHF (290 mE) was added over 10 mm maintaining a temperature of <-60 C. The reaction mixture was allowed to warm to 0 C. over 1 hand then quenched with aqueous ammonium chloride (500 mE, 13 wt %). The resulting layers were separated and the organic layer was washed with brine (400 mE). The organic layer was dried over Mg504, filtered, and concentrated. The residue was taken up in acetone (200 mE) and allowed to stir for 2 h. The resulting suspension was filtered and washed with acetone (20 mE). After drying in a vacuum oven at 60 C. the title compound was obtained as a white solid. ?H NMR (400 MHz, CDC13) oe ppm 8.24 (d, J=2.2 Hz, iH), 7.72 (d, J=8.7 Hz, iH), 7.54-7.47 (m, 3H), 7.42-7.33 (m, 3H), 7.06 (s, iH), 5.97 (s, iH), 4.32-4.22 (m, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.32 (s, 3H), 2.13 (s, 3H); MS mle 557.1 (M+H). (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl) quinolin-6-yl)(i ,2-dimethyl- 1 H-imidazol-5-yl)(i -methyliH-i,2,3-triazol-5-yl)methanol was resolved into its constituent enantiomers by chiral HPEC [Chiralcel OD, mobile phase: 85% heptane, 15% ethanol]. Afier resolution, the individual enantiomers were crystallized from acetone (7.5 mE/g) and isolated by filtration after the addition of heptane (15 mE/g). The first eluting enantiomer was Example 80B: ?H NMR (400 MHz, CDC13) oe ppm 8.23 (d, J=2.2 Hz, iH), 7.72 (d, J=8.8 Hz, iH), 7.51 (d, J=8.2 Hz, 2H), 7.43-7.33 (m, 3H), 7.05 (s, iH), 6.99 (bs, iH), 6.01 (s, iH), 4.30 (s, 2H), 4.06 (s, 3H), 3.88 (s, 3H), 3.34 (s, 3H), 2.17 (s, 3H); MS mle 557.1 (M+H). The second eluting enantiomer was Example 80C:?H NMR (500 MHz, CDC13) oe ppm 8.19 (d, J=2.2 Hz, iH), 7.74 (d, J=8.7 Hz, iH), 7.52 (d, J=8.2 Hz, 2H), 7.43-7.35 (m, 3H), 7.14 (s, iH), 6.08 (s, iH), 5.32 (bs, iH), 4.33 (s, 2H),4.07 (s, 3H), 3.91 (s, 3H), 3.38 (s, 3H), 2.28 (s, 3H); MS mle557.1 (M+H). 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.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

Three-necked flask,In the presence of nitrogen,31.8 g (300 mmol) of sodium carbonate,28.2 g (100 mmol) of 1- (1-trifluoromethanesulfonate) ethyl-2,3-dimethylbenzene,[1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride 3.5 g (5 mmol),Imidazole (8.2 g, 120 mmol) and 52 ml of [BuPy] BF4,The reaction was stirred at 70 C for 30 minutes,After monitoring the reaction,Pour into the water,Dichloromethane extraction,The organic phase was washed three times,Dry the organic phase over anhydrous sodium sulfate,Concentrated under reduced pressure,The petroleum ether was recrystallized to obtain 17.6 g of 4- [1- (2,3-dimethylphenyl) ethyl] -1H-imidazole,Yield 84.7%(S) -4- [1- (2,3-dimethylphenyl) ethyl] -1H-imidazoleee value of 79.89%.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Chenda Biological Technology Co., Ltd.; Lv Yanhua; (6 pag.)CN106588779; (2017); 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. 5465-29-2, name is 2-Propylbenzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H12N2

General procedure: To a stirred solution of 10.0 mmol of compound 1a-1i in 10 mL of conc. H2SO4 we added dropwise 10 mL (0.11 mmol) of 33% aqueous hydrogen peroxide at 100-105C. The mixture was stirred for 0.5 h at 120C, let to cool down, and poured in water. The pH of the solution was adjusted to ~2 with sodium carbonate, and the precipitate of 2-alkylimidazole-4,5-dicarboxylic acid 2a-2i was filtered off and recrystallized from water.

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 5465-29-2.

Reference:
Article; Brusina; Gubina, Yu. A.; Nikolaev; Ramsh; Piotrovskii; Russian Journal of General Chemistry; vol. 88; 5; (2018); p. 874 – 878; Zh. Obshch. Khim.; vol. 88; 5; (2018); p. 729 – 733,5;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem