Category: imidazoles-derivatives

Some common heterocyclic compound, 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, molecular formula is C13H11N3, 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: 2963-77-1

General procedure: A suspension of amine A1-A3 (1 mmol) in water is takenin a round bottomed flask; to this sulphonyl chloride(1 mmol) was added. This was stirred at room temperature while monitoring the reaction. The product was filtered,recrystallised using methanol-water and column purified.The structures were confirmed by 1H NMR, 13C NMR, IRand mass spectral analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2963-77-1, its application will become more common.

Reference:
Article; Vangala, Radhika; Sivan, Sree Kanth; Peddi, Saikiran Reddy; Manga, Vijjulatha; Journal of Computer-Aided Molecular Design; vol. 34; 1; (2020); p. 39 – 54;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Adding clinfloxacin (500 mg, 1.37 mmol) to a 150 mL round bottom flask,Diethyl phosphite (451.28 mg, 4.10 mmol), benzimidazole-2-carbaldehyde (299.40 mg, 2.05 mmol) and toluene (50 mL) were stirred and refluxed at 120 C for 6 hours, and thin layer chromatography was followed until the reaction was completed. . After concentration, extraction, column chromatography separation,After recrystallization, drying, etc., the compound I-11 is obtained.(297.46 mg). Yield: 34.4%; yellow powder;

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

Reference:
Patent; Southwest University; Zhou Chenghe; Wang Liangliang; Xu Jiahe; Zhao Wenhao; Ba Tini·nasaiya; (19 pag.)CN110041368; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products 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.

General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.

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

Reference:
Article; Gou, Gao-Zhang; Wu, Na; Zhang, Ju-Cheng; Shi, Ling; Liu, Gui-Yang; Liu, Wei; Mang, Chao-Yong; Chi, Shao-Ming; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 57A; 2; (2018); p. 181 – 185;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-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 693-98-1, name: 2-Methyl-1H-imidazole

Under a protection of N2, 0.25 mol of potassium carbonate, 0.5 mol of 2-methylimidazole and 0.6 mol of acrylonitrile were added to 60 mL of anhydrous methanol in a 250 ml three-neck round bottom flask, and the mixture was stirred under reflux in an oil bath at 60 C for 12 h. Complete reaction; After the reaction was stopped, the unreacted raw materials and methanol were removed by rotary evaporation, and dried under vacuum at 70 C for 24 hours to obtain a yellow transparent liquid. It is 1-nitrileethyl-2-methylimidazole. The yield was 82%.

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

Reference:
Patent; Hebei University of Technology; Zhang Wenlin; Wang Yuxin; He Jiaming; Zhao Yongqi; Huo Yu; Li Chunli; (12 pag.)CN108976169; (2018); A;,
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. 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H9F3N2O2

3-(4-Methyl-imidazol-l-yl)-N-{4-methyl-3-[3-methyl-3-(7H-pyrrolo[2,3- d1pyrimidin-4-ylVureido1-phenvU-5-trifluoromethyl-benzamide [00104] To a solution of 7 (7 mg, 0.23 mmol, 1.0 eq.), 3-(4-Methyl-imidazol-l- yl)-5-trifluoromethyl-benzoic acid (7.6 mg, 0.27 mmol, 1.2 eq.), and DIPEA (40 mul, 0.27 mmol, 1.2 eq.) in DMF (0.5 ml) is added HATU (9.9 mg, 0.25mmol, 1.1 eq.). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImI). The resulting solution is subjected to purification by reverse- EPO phase LC-MS to yield the title compound as a TFA salt: 1H NMR 400 MHz (DMSOd6) delta 1H NMR 400 MHz (DMSOd6) delta 12.81 (bs, IH), 12.28 (bs, IH), 10.52 (bs, IH), 9.40 (s, IH), 8.52 (s, IH), 8.51 (s, IH), 8.40 (d, J = 2.0 Hz, IH), 8.36 (s, IH), 8.33 (s, IH), 7.48 (m, 2H), 7.19 (d, J = 8.32 Hz, IH), 6.78 (m, IH) 3.05 (s, 3H), 2.30 (s, 3H) 2.27 (s, 3H); MS m/z 549.2 (M + 1).

The synthetic route of 641571-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM, LLC; WO2006/124462; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, 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.

A sealed tube is charged with tert-butyl 4-(p-tolylsulfonylhydrazono)- piperidine-1-carboxylate (1284.79 mg; 3.50 mmol; 1 .10 eq.), CS2CO3 (1553.44 mg; 4.77 mmol; 1 .50 eq.). The tube is RM is sealed, purged with argone and then 1 ,4-dioxane (12.00 mL) and 1 -methyl-1 – -imidazole-4- carbaldehyde (350.00 mg; 3.18 mmol; 1.00 eqf.) are added. RM is heated at 1 10C for 48 h. After this time, the mixture is filtered through a Celite pad and then the solvent is evaporated. Crude product is purified by FCC (hexane/EtOAc; gradient) to afford 4-(1 -methyl-1 H-imidazole-4-carbonyl)- piperidine-1 -carboxylic acid tert-butyl ester (483.90 mg; yield 51.0 %; 98% by UPLC) as a beige solid

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

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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 312-73-2 as follows. COA of Formula: C8H5F3N2

General procedure: In a typical experimental procedure, a dry, two-necked, 50 mL round bottomed flask was charged with 5 mL of dry MeCN, 1.0 mmol of benzimidazole derivatives and 1.0 mmol of NaH. The solution was stirred at room temperature for 30 min, then a solution of 2,2,2-trifluoro acetimidoyl chloride derivatives (1.0 mmol in 2 mL of dry MeCN) was added dropwise via a syringe. The mixture was stirred at room temperature appropriate time and then filtered. After removing the solvent under reduced pressure, the crude product was purified by preparative thin-layer chromatography on silica gel [eluent: n-hexane/EtOAC, 3:1] to give the products. The products obtained from 2-mercapto benzimidazole and 2-mercapto-1-methyl imidazole were purified by washing with n-hexane.

According to the analysis of related databases, 312-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Darehkordi, Ali; Rahmani, Fariba; Journal of Fluorine Chemistry; vol. 190; (2016); p. 41 – 47;,
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. 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C22H17BrN2

Example 226: N-[3-(1H-imidazol-4-yl)phenyl]-1-oxo-2,3,4,5-tetrahyd][1,4]diazepino[1,2-a]indole-8-carboxamide Step 1: Synthesis of 3-(l-trityl-1H-imidazol-4-yl)aniline (3-Aminophenyl)boronic acid (1.0 g, 7.3 mmol), 4-bromo-1-trityl-1H-imidazole (2.8 g, 7.3 mmol), tri-i-butylphosphonium tetrafluoroborate (424 mg, 1.5 mmol) and KF (1.4 g, 24.1 mmol) are added into dry THF (20 mL) and argon is bubbled through the mixture for 10 min. Tris-(dibenzylideneacetone) dipalladium(O) (669 mg, 0.7 mmol) is added and the reaction mixture is sealed and heated at 60 C for 16 h. The solid is filtered and the filtrate is diluted with EtOAc (250 mL). The solution is washed with water (3×100 mL), brine (100 mL), dried (Na2S04) and concentrated. The crude material is purified by flash column chromatography using methanol in CH2C12 to afford the title compound (1.1 g, 36%).

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 87941-55-7.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); 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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-89-2

4-iodo-1H-imidazole (Compound 13, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)below freezing,Triethylamine (2.1 mL, 15 mmol),Trityl chloride (3.4 g, 12 mmol) was added,Under an argon gas atmosphere,And the mixture was stirred at room temperature (25 C.) for 17 hours.After completion of the reaction,Add water,Extraction was carried out twice with dichloromethane.The combined dichloromethane layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure,The obtained crude product was purified by silica gel column chromatography (eluent (volume ratio): chloroform / n-hexane = 1/1 ? chloroform) to obtain Compound 14 (4.1 g, 9.3 mmol, yield 93%).

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; OKUMURA, YUKI; IZAWA, AKIHIRO; AKAMA, KEI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (27 pag.)JP2015/110563; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH. 14a:yellow powder, 65%; mp 221-222 C; 1H NMR (200 MHz,DMSO-d6) delta 9.34 (s, 1H, CHazomethine), 8.18 (d, J = 7.3 Hz,2H, Ar), 7.68-7.48 (m, 7H, Ar, C5NH2 ), 7.31-7.10 (m, 8H,Ar), 5.34 (s, 1H, C7H); 13C NMR (125 MHz, DMSO-d6) delta162.4 (3), 149.5 (Cazomethine), 143.8 (C5), 138.3, 135.3, 133.3,133.0, 132.5, 132.1, 130.4, 129.5, 129.4, 128.8, 128.2, 128.1,127.4, 125.8, 117.9 (N), 71.7 (C6), 45.01 (C7); MS (m/z) (%):429 ([M+?], 25), 285 (100), 194 (19), 104 (26), 77 (19), 43 (25);anal. calcd for C28H23N5 (429.53) C, 78.30; H, 5.40; N, 16.31;found: C, 80.25; H, 5.70; N, 13.41.

The synthetic route of 6775-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem