Imidazoles-derivatives

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, Product Details of 6160-65-2

A solution of the amine (0.1 10 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 muIota_, 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%).

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

Reference:
Patent; DUKE UNIVERSITY; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; LIEDTKE, Wolfgang; STEINHOFF, Martin; GUILAK, Farshid; (150 pag.)WO2016/28325; (2016); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O2

A solution of [1H-IMIDAZOLE-4-CARBOXYLIC] acid methyl ester (1.0 g, 7.93 mmol) in [N, N] dimethylformamide at [25 oC] was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 [MMOL).] The reaction was stirred at [25 oC] for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a IN aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60,230- 400 mesh, 50: 50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4- carboxylic acid methyl ester (2. [88] g, 98.6%) as a white foam

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 17325-26-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2003/106459; (2003); 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 29043-48-9 as follows. SDS of cas: 29043-48-9

To a stirred solution of 2-methyl-1 H-benzo[d]imidazol-5-amine (187 mg) in DCM (5 mL) at 0 C was added 3-carbamoyl-4-hydroxybenzene-1 -sulfonyl chloride (lnt-1 , 300 mg). The reaction mixture was allowed to warm to RT and stirred for 16 hr. The reaction mixture was diluted with water (30 mL) and extracted with DCM (2 x 50 mL). The combined DCM extracts were washed with saturated brine (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product (300 mg). The crude product was purified by reversed phase preparative HPLC (Sunfire C18, 30 x 250 mm) using a gradient of 10-100% acetonitrile in 10 mM ammonium bicarbonate (aq). The desired fraction was concentrated under reduced pressure and the resulting solid was collected by filtration, washed with water (10 mL) and dried under vacuum to afford the titled compound (55.6. mg). LCMS m/z 347.04 (M+H)+. NMR after D20 exchange (400 MHz, DMSO-c/6) delta ppm 2.27 – 2.50 (m, 3 H) 6.76 (d, J=8.33 Hz, 1 H) 6.85 (dd, J=8.55, 1 .75 Hz, 1 H) 7.02 – 7.21 (m, 1 H) 7.28 (d, J=8.33 Hz, 1 H) 7.40 – 7.61 (m, 1 H) 8.19 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 29043-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 150058-27-8, name is Methyl 2-ethoxy-1H-benzo[d]imidazole-7-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. SDS of cas: 150058-27-8

BIM (20 g, 1 eq) was dissolved in dimethylacetamide:methanol [(1:4), (100 mL, 5 vol)], potassium carbonate (18.8 g, 1.5 eq) was added thereto, and the mixture was stirred at 25¡ãC – 30¡ãC for 15 min. Furthermore, BCL (34.4 g, 1.05 eq) and tetrabutylammonium iodide (1.67 g, 0.05 eq) were added thereto, and the mixture was stirred at the same temperature for 26 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of BIM was confirmed. To the reaction mixture was added water (200 mL, 10 vol), the mixture was stirred for 2 hr, and the precipitated pink solid was filtered. The obtained solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and blast dried at 50¡ãC – 55¡ãC for 4 hr to give a mixture of crude CBME and compound 37 (49 g, CBME:compound 37=6:1 (molar ratio)). The crude product was directly used for the next step (4).

The synthetic route of Methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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 aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic Fe3O4-TiO2/Cu2O (0.010 g equal to 1.4 mol% Cu2O) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and diluted by ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water and dried over anhydrous MgSO4. The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent 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, its application will become more common.

Reference:
Article; Nemati, Firouzeh; Elhampour, Ali; Research on Chemical Intermediates; vol. 42; 10; (2016); p. 7611 – 7624;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 25 cm3 round bottomed flask, 0.20 mol% of ruthenium(II) catalyst, 2 mmol of alcohol and amine substrates, 15 mol% of potassium tert-butoxide (KtBuO) were placed and dissolved in 2.0 cm3 of toluene. The reaction flask was kept at 120 C for 12 h in an oil bath. Upon completion of reaction (monitored by TLC), the solvent was removed under vacuum and the resulting residue was purified by column chromatography on silica gel using ethylacetate/n-hexane. The amide products were dried overnight under vacuum. The resulting amides were identified by comparison of the 1H and 13C NMR data with those previously reported (ESI? )

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

Reference:
Article; Selvamurugan, Sellappan; Ramachandran, Rangasamy; Prakash, Govindan; Nirmala, Muthukumaran; Viswanathamurthi, Periasamy; Fujiwara, Shoji; Endo, Akira; Inorganica Chimica Acta; vol. 454; (2017); p. 46 – 53;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

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

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2403-66-9, A common heterocyclic compound, 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, molecular formula is C10H12N2O, 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: The benzimidazole was dissolved in acetonitrile. Allyl bromide (1.1 equiv) was added and the mixture was heated in the microwave to 150 C for 2 minutes. Celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.

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; THORPE, Steven Brandon; SANTOS, Webster L.; LYNCH, Kevin R.; (375 pag.)WO2017/172989; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34: Preparation of intermediate 8: 1-(1 -trityl-1 W-imidazol-4-yl)ethanolTo a solution of 1 -trityl-1 H-imidazole-4-carbaldehyde (10.0 g, 0.03 mol) in anhydrous THF (100 mL) was added dropwise methyl magnesium bromide (1.4 M in hexane, 52.8 mL, 0.075 mol) at O0C. After the addition, the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NH4CI (50 mL) and the mixture extracted with CH2CI2 (3*50 mL). The organic layers were combined, washed with 1 N aq. NaOH (3chi20 mL), water (3chi20 mL) and brine (100 mL), dried over MgSO4 and evaporated. The residue was purified via column chromatography {silica gel, EtOAc/Petroleum ether 1 :5) to yield the title compound (8.0 g, 75.0%) as a white solid.

The synthetic route of 1-Trityl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4096; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, 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 39070-14-9 as follows.

A mixture of 2-(1-methyl-5-nitro-1H-imidazol-2-yl)-ethanol (1.32 mmol) and 1-fluoro- 3 -nitrobenzene (1.67 mmol) and K2C03(465 mg, 3.36 mmol) in DMF (5 mL) was stirred 2 hours at ambient temperature followed by heating. The reaction was worked-up by extraction. The residue was purified by prep-HPLC with the following condition: column: XBridge preparative CI 8 OBD column 19x 150 mm, 5 um; mobile phase A: water (10 mmol/L NH4HCO3), mobile phase B: ACN; flow rate: 20 mL/min; gradient elution. The product-containing fractions were collected and then lyophilized to give l-methyl-5-nitro-2-(3-nitro-phenoxymethyl)-lH- imidazole. LC-MS: (ES, m/z) 279.07 (M+H)+; analysis: C, 47.53; H, 3.69; N, 20.24; O, 28.85.

According to the analysis of related databases, 39070-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem