Category: imidazoles-derivatives

Related Products of 1072-63-5, These common heterocyclic compound, 1072-63-5, name is 1-Vinyl-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.

1-Vinylimidazole (5 g, 53.1 mmol) was taken in a 100-mL round-bottomedflask. To this, n-bromoethane (6.947 g, 63.7 mmol) was added andheated at 60 C for 3 h to produce 1-vinyl 3-ethylimidazolium bromide[ViEIm]Br in quantitative yields.

Statistics shows that 1-Vinyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-63-5.

Reference:
Article; Pothanagandhi, Nellepalli; Sivaramakrishna, Akella; Vijayakrishna, Kari; Reactive and functional polymers; vol. 106; (2016); p. 132 – 136;,
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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

156.3 mg of the compound obtained in Synthesis Example 29-2 was dissolved in 2 ml of methanol, and then 2 ml of a 4 mol/l hydrochloric acid/dioxane was added to the solution, followed by stirring for 165 minutes at room temperature. On completion of the reaction, the solvent was distilled off. Subsequently, it was dissolved in 4 ml of anhydrous methanol, and then 131.1 mul of triethylamine and 62.8 mg of 1-methyl-2-formylbenzimidazole were added to the solution and the whole was stirred for 12 hours at room temperature. After the solvent was distilled off, subsequently, 4 ml of anhydrous methanol was added thereto and the whole was cooled to 0°C. Then, 19.8 mg of sodium borohydride was added to the solution and the whole was stirred for 30 minutes while being gradually returned to room temperature. On completion of the reaction, the solvent was distilled off and the residue was purified by means of silica gel column chromatography (10 g, chloroform/methanol = 10/1). After the resultant compound was dissolved in 2 ml of a 1 mol/l hydrochloric acid, water was distilled off. Consequently, 44.1mg of hydrochloride of the above-mentioned compound was obtained as a white-red solid product. MS(FAB,Pos.):m/z=642[M+1]+1H-NMR(500MHz,DMSO-d6):delta=1.73-1.91(4H,m),2.09(2H,br),3.64(3H,s ),3.85(3H,s),4.08-4.12(2H,m),4.38-4.43(2H,m),4.47-4.59(3H,m), 4.76-4.77(2H,m),5.98-5.99(1H,m),6.22-6.23(1H,m),6.79-6.80(1H, m),7.29-7.59(6H,m),7.60-7.73(2H,m),7.84-7.86(1H,m),7.94-8.08 (4H,m), 8.70-8.72 (2H,m), 8.96 (2H,br).

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 3012-80-4.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1389460; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

Lithium hexamethyldisilazide (iM in tetrahydrofuran, 2i.4 ml, 2i.4 mmol) was added dropwise over iS mm to a stirred, cooled (-iO C) suspension of ethyl 4-methyl-i H25 imidazole-S-carboxylate (3.00 g, i9.S mmol) in dry dimethylformamide (200 ml) underan atmosphere of argon. After stirring for a further iO mi 0- (diphenylphosphoryl)hydroxylamine (5.45 g, 23.4 mmol) was added and the mixture was warmed to room temperature. After 6 h, water was added until a clearhomogeneous solution formed and subsequently the mixture was evaporated todryness. The resultant solid was treated with dichloromethane and the mixture wasfiltered and the filter cake was washed with further portions of dichloromethane. Thecombined filtrate and washings were evaporated to give a solid which was purified byflash chromatography (methanol-dichloromethane gradient, 0:100 rising to 5:95) togive 1.75 g (10.3 mmol, 53% yield) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, Chloroform-d) ppm 7.59 (s, 1H), 5.33 (br s, 2H), 4.37 (q, 2H, J =7.4 Hz), 2.46 (s, 3H), 1.40 (t, 3H, J = 7.4 Hz).UPLC/MS (3 mm) retention time 0.56 mm.LRMS: m/z 170 (M+1).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; CONNOLLY, Stephen; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; MORENO MOLLO, Immaculada Montserrat; ROBERTS, Richard Spurring; SEVILLA GOMEZ, Sara; (216 pag.)WO2017/60488; (2017); 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 288-32-4 as follows. name: 1H-Imidazole

General procedure: General Procedure for Ultrasound-Promoted Iodination of Aromaticand Heteroaromatic Compounds: Hydrogen peroxide 30% (m/v) (4-8 mmol) was added to a suspension of theappropriate aromatic or heteroaromatic compound (1a-q) (2 mmol) and moleculariodine (2-4 mmol) in distilled water (10 mL). The mixture was sonicated and the progressof reaction was monitored by thin-layer chromatography (TLC). Afterward, asaturated sodium thiosulfate aqueous solution (10 mL) was added to the mixture,which was extracted with ethyl acetate (320mL). The organic phase was dried overMgSO4. After filtration, the solvent was evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel using an appropriate eluent,affording the desired product (2a-q).

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ferreira, Irlon M.; Casagrande, Gleison A.; Pizzuti, Lucas; Raminelli, Cristiano; Synthetic Communications; vol. 44; 14; (2014); p. 2094 – 2102;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7,Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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 solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

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

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9, 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 32673-41-9 as follows.

Step A Preparation of 1-triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

According to the analysis of related databases, 32673-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dinsmore, Christopher J.; Bergman, Jeffrey M.; US2002/10184; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Intermediate le 5-Iodo- l-(2,2,2-trifluoroethyl)- lH-imidazole In a 50 mL three-necked flask, 4-iodo-lH-imidazole (0.500 g, 2.58 mmol, Eq: 1.00) was combined under Ar with THF (7 ml) to give a colorless solution. Sodium hydride 55% (337 mg, 7.73 mmol, Eq: 3) was added at 0C (exothermic reaction, temperature rose to 17C). The reaction mixture was stirred at RT for 30 min. and then cooled down again to 0C, before 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.2 g, 5.16 mmol, Eq: 2), dissolved in THF (3 ml), was added. The white suspension was stirred at RT for additional 1.5 hours when TLC indicated that the reaction was complete. Work up: The reaction mixture was poured into 10 mL H20 and extracted with EtOAc (2 x 15 mL). The organic layers were combined, washed with brine, dried over Na2S04, and concentrated i. V. Purification : The crude product was purified by flash chromatography (silica gel, 70 g, 0% to 60% EtOAc in heptane) to yield 80 mg of the desired title compound as off-white solid, besides 619 mg of the unwanted 4-iodo-l-(2,2,2-trifluoro-ethyl)-lH-imidazole. MS (ESI): 276.9 [M+H]+.

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans, P.; MAYWEG, Alexander, V.; MOHR, Peter; TAN, Xuefei; WO2013/120771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 21 (0.212 g, 1.12 mmol), CuI (20 mg, 0.112 mmol), (PPh3)2PdCl2 (40 mg, 0.056 mmol) and triethylamine (0.23 mL, 1.68 mmol) in acetonitrile (10 mL) was added 1-(4-bromophenyl)imidazole (0.5 g, 2.24 mmol). The reaction mixture was recharged with argon and stirred at 80 C for 3 h in a sealed tube. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine. The organic solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (CH2Cl2/PE/NH3?H2O, 8:3:0.1) to afford 22c (0.3354 g, 1.01 mmol, 90.2%).HRMS (ESI) (M+H)+ m/z 332.1389, Calcd for C20H18N3O2 332.1394. 1H NMR (CDCl3, 400 MHz), delta: 7.93 (s, 1 H, H-imidazolyl), 7.55 (d, J = 8.1 Hz, 2 H, H-phenyl), 7.45-7.29 (m, 9 H, H-imidazolyl, H-phenyl), 5.25-5.15(m, 3 H, -NH-, -CH2-O-), 4.28 (s, 2 H, -NH-CH2-).

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

Reference:
Article; Li, Xue-Meng; Lv, Wei; Guo, Si-Yang; Li, Ya-Xin; Fan, Bing-Zhi; Cushman, Mark; Kong, Fan-Sheng; Zhang, Jun; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 235 – 254;,
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. 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H9N3O3

Synthesis of SYN-E; Formation of the dispersion synergist SYN-E was accomplished by diazotation of compound 7 and subsequent coupling with compound 3. [Show Image] 17.3 g (0.1 mol) of compound 7 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 98 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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 6160-65-2, Computed Properties of C7H6N4S

[00241] A solution of the amine (0.110 g, 0.43 mmol) in anhydrous CH2CI2 (2 ml_) was added dropwise over 2-5 minutes to an ice-salt bath cooled solution of 1 , 1′-thiocarbonyldiimidazole (95%, 0.162 g, 0.87 mmol, 2 eq.) in anhydrous CH2CI2 (6 ml_). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours after which time analysis by TLC (10% MeOH in CH2CI2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (620 mu, 4.3 mmol, 10 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (~1 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf Si02 (40 g), 100% CH2CI2? 10% MeOH in CH2CI2) gave the thiourea as an amber oil that solidified upon standing (0.130 g, 97%).

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, 1,1′-Thiocarbonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DUKE UNIVERSITY; LIEDTKE, Wolfgang; (189 pag.)WO2017/177200; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem