Category: imidazoles-derivatives

Reference of 934-32-7, These common heterocyclic compound, 934-32-7, name is 1H-Benzo[d]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 requested benzylic aldehyde (1 mmol),2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol),beta-diketone (1 mmol) and NS-C4(DABCO-SO3H)2·4Cl(20 mg, 10 mol %) was heated at 90 C under solvent-freeconditions. The progress of the reaction was monitoredby TLC (n-hexane: EtOAc, 70:30). After completion ofthe reaction, the reaction mixture was cooled to roomtemperature and 3 mL of water was added to it. Thecatalyst was dissolved in water and filtered for separation ofthe crude product. The separated product was washed twicewith water (2 × 5 mL), and the crude product was purifiedby recrystallization in ethanol.

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Journal of the Iranian Chemical Society; vol. 14; 11; (2017); p. 2275 – 2286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-32-7, 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. 934-32-7 name is 1H-Benzo[d]imidazol-2-amine, 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.

To the mixture of 2-aminobenzimidazole (1 mmol), malononitrile (1 mmol) and 4-fluorobenzaldehyde (1 mmol) in ethylene glycol (5 mL), SSA (42.6 mg, 0.11 mol %) wasadded. The mixture was heated at 50 C for 5 minutes. After completion of the reaction(TLC), 10 mL EtOAc was added to the reaction mixture and the catalyst was recovered by filtration. The organic layer was dried over Na2SO4; the solvent was evaporated and purified by recrystallization from ethanol to give compounds 1b. Yield 87%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Basyouni, Wahid M.; Abbas, Samir Y.; Abdelazeem, Nagwa M.; El-Bayouki, Khairy A. M.; El-Kady, Mohamed Y.; Synthetic Communications; vol. 49; 22; (2019); p. 3112 – 3120;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4278-08-4,Some common heterocyclic compound, 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole, molecular formula is C9H7FN2, 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.

Into a 15mL pressure tube, sequentially add 1e (48.6 mg, 0.3 mmol), dichloromethane (3 mL), 2a (84.7 mg, 0.45 mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7 mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3e (57.5 mg, 55%) as a white solid.

The synthetic route of 4278-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Amine 2ah (1.34g, 6mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.78 g, l equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (900 mg, 6 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 750 mg of a white solid. Yield = 31% ‘HNMR (DMSO, 200 MHz) delta 1.58 (2H, m), 1.66 (4H, m), 2,78 (4H, M), 4.32 (2H, d, J = 6 Hz), 6.63 (1H, dd), 6.73 (1H, t), 6.94 (1H, t), 6.95 (1H, dd), 7.06 (2H, m), 7.29 (1H, d), 8.35 (1H, bs), 10.05 (1H, bs), 10.60 (1H, bs); [M+1] 400.2 (C20H22CIN5O2 requires 399.87)

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

Synthetic Route of 4856-97-7, 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. 4856-97-7 name is (1H-Benzoimidazol-2-yl)methanol, 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.

Starting from the o-phenylenediamine compound (1.0equiv) and glycolic acid (2.0equiv), the reaction was refluxed in the presence of a 4.0 mol/L aqueous hydrochloric acid solution, and the TLC was traced until the reaction of the starting material was complete, and the reaction solution was cooled. To room temperature,Adjusting the pH to 7 with 20% NaOH, standing to precipitate a solid, suction filtration, and drying to obtain compound 5; transferring compound 5 to a round bottom flask,Add NaOH aqueous solution,KMnO4 (2.5 equiv) was added in portions at 80 C with stirring, and the reaction was continued after the addition.After all the raw materials were completely reacted, the reaction solution was cooled to room temperature, and the filtrate was filtered by suction.Adjust the pH to neutral with 20% aqueous HCl solution to precipitate a solid.Drying by suction filtration to obtain compound 6;Compound 6 with DMF(1.0equiv) dissolved, then added 1-hydroxybenzotriazole (HOBt, 1.1equiv)And 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 equiv),The reaction was stirred at room temperature for 30 min, and then compound 4 (1.1 equiv) was added to the reaction solution.Continue to stir the reaction,The TLC traces to the completion of the reaction of the starting material, and the reaction solution is poured into ice water.It was then extracted with ethyl acetate and the organic layer was evaporated.The crude product was purified by column chromatography to give the allyl intermediates Sb.

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

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 822-36-6, 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. 822-36-6, name is 4-Methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

4-Fluoro-3-methoxybenzaldehyde (85 g, 0.55 mol), 4-methyl-1 /-/-imidazole (90.5 g,1.1 mol) and cesium carbonate (268.8 g, 0.82 mol) were combined in dimethylformamide (1.7 L) and stirred at 100 0C for 1 hour. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in water (2 L) and extracted with ethyl acetate (3 x 2 L). The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. Chromatography on silica (Eluant: 2:1 petroleum ether: ethyl acetate) afforded a yellow solid, which was recrystallized from ethyl acetate (300 mL) to provide the title compound as a white solid. Yield: 17.8 g, 0.082 mol, 15%. 1H NMR (300 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.97 (s, 3H), 7.01 (m, 1H), 7.45 (d, J=7.8 Hz, 1 H), 7.54-7.58 (m, 2H), 7.83 (d, J=1.3 Hz, 1 H), 10.01 (s, 1 H).

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1402838-08-7,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.

[402] To a solution of compound 1.1 (500 mg, 1.2 mmol) and 1-(adamantan-1-yl) ethanone (235 mg, 1.3 mmol) in a mixed solvent of ethanol (5 mL) and THF (5 mL) was added sodium ethoxide (122 mg, 1.8 mmol). The resulted mixture was stirred at room temperature for overnight, then the mixture was added water (30 mL), and extracted with ethyl acetate (60 mLx2). Then the combined organic phase was washed with brine, dried oversodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate= 2:1) to afford compound 1.2 (400 mg, yield: 62%) as a white solid.[403] m/z: [M+H] 575

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO.,LTD.; LI, Qun; GAO, Daxin; (158 pag.)WO2016/131380; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, molecular formula is C7H10N2O2, 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: 30148-21-1

General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10% NaHCO3 solution, extracted with ethyl acetate (2×100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 30148-21-1, its application will become more common.

Reference:
Article; Venkat Ragavan; Vijayakumar; Rajesh; Palakshi Reddy; Karthikeyan; Suchetha Kumari; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4193 – 4197;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 670-83-7,Some common heterocyclic compound, 670-83-7, name is 2,5-Diphenyl-1H-imidazole, molecular formula is C15H12N2, 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.

EXAMPLE 3 2,5-diphenyl-4-hydroxymethyl-imidazole hydrochloride 5 g (0.0227 mole) of 2,4-diphenyl-imidazole, 0.85 g (0.0283 mole) of paraformaldehyde and 0.1 g of finely ground potassium hydroxide are dissolved in 29 ml of warm methanol and heated under reflux for 90 hours. The solution is then decolourized with activated carbon, filtered and dried. Water and chloroform are added to the residue by stirring; the insoluble solid of both the layers is filtered, washed with water and chloroform and dried. 2.8 g (yield 49.3%) of crude product is thus obtained, which is crystallized from methanol to afford 1.1 g of 2,5-diphenyl-4-hydroxymethyl-imidazole, m.p. 206-207 C. (dec.) By the usual techniques the hydrochloride has been obtained, m.p. about 220 C. (dec.).

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

Reference:
Patent; Zambon S.p.A.; US4560696; (1985); 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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

To a suspension of 4-bromo-3-chloro-5-(trifiuoromethyl)aniline (15 g, 54.7 mmol, APAC) in CH2C12 (200 ml) was added 1 ,1 ‘-thiocarbonyldiimidazole(l 1.7 g, 65.6 mmol) at 0 C. The reaction was stirred cold for 30 minutes and then at RT overnight. The reaction mixture was concentrated and the crude material was purified by flash chromatography (silica gel, 220g, 5% to 15%) DCM/Hexanes) to give a yellow oil as desired product (12.3g, 71% yield).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BILOTTA, Joseph Anthony; CHEN, Zhi; CHIN, Elbert; DING, Qingjie; ERICKSON, Shawn David; GABRIEL, Stephen Deems; KLUMPP, Klaus; MA, Han; MERTZ, Eric; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/6066; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem