Imidazoles-derivatives

Application of 152628-03-0, The chemical industry reduces the impact on the environment during synthesis 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, I believe this compound will play a more active role in future production and life.

7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (10.000 g, 0.045 M) was dissolved in ethanol (50 mL) using a stir bar in a two neck round bottom flask connected to a Liebig condenser. By maintaining the flask at 0-5C thionyl chloride (26.700 g, 0.225 M) was added via dropping funnel. Then the reaction was allowed to reflux for 3-3.5 h. The progress of the reaction was monitored by TLC (using 9.5:0.5 ethyl acetate & methanol mobile phase). After TLC analysis revealed the completion of reaction, excess ethanol and thionyl chloride was stripped under vacuum at 60C. Further reaction mixture was washed with 20 mL of toluene to remove traces of thionyl chloride. Furthermore, 50 mL of toluene was added and reaction mixture was maintained at 0-5 C to get off white precipitate. Then later, the precipitate was stirred for 0.5 h, filtered and washed with toluene (50 mL). Then solid (HCl salt) was dissolved in dichloromethane (60 mL) and pH was adjusted to 7 by addition of 20 % NaHCO3 (12 grams in 60 mL demineralized water). Then dichloromethane layer was washed with 20 mL demineralized water. Dichloromethane was removed under vacuum to get oil which upon cooling afforded the solid. Yield = 8.000 g (71%).

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-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mallandur, Bhargava K.; Rangaiah, Gururaja; Harohally, Nanishankar V.; Synthetic Communications; vol. 47; 11; (2017); p. 1065 – 1070;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C22H17IN2

To a suspension of 4-iodo-1 -trityl-imidazole (3.00g, 6.88mmol) in THF (55 ml_) at 0C was slowly added isopropylmagnesium chloride (8.6ml_, 17.19mmol), the clear solution was then left to stir for 10 minutes. Trimethyl borate (3.83ml_, 34.38mmol) was added portion wise and the reaction mixture was left to stir for 10 minutes at 0C before being allowed to reach room temperature and stir for a further 10 minutes. 1 M HCI (30 ml_) was then added and the reaction was stirred for 10 minutes. The reaction was quenched by pouring it slowly in to a saturated solution of NaHC03 solution (100 ml_) which was then extracted with EtOAc (3 x 50 ml_). The combined organic phases were then dired over Na2S04 and concentrated in vacuo to give the crude product (1 -tritylimidazol-4-yl)boronic acid (2.53g, 7.15mmol, 103.92% yield) as an off white solid. MS Method 2: RT 1 .47 min, ES+ m/z 355 [M+H]+ H NMR (400MHz, DMSO) delta/ppm: 7.20-7.45 (m, 10H), 6.95-7.10 (m, 7H).

According to the analysis of related databases, 96797-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; BHAMRA, Inder; BINGHAM, Matilda; TESTAR, Richard; SARGENT, Louise; DONOGHUE, Craig; (128 pag.)WO2016/55786; (2016); 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Intermediate 55: step b bis(1-methyl-1H-imidazol-5-yl)methanone To a solution of 5-bromo-l -methyl- IH-imidazole (1.2 g, 7.45 mmol) in DCM (10 mL) was added ethyl magnesium, bromide (2.5 mL, 7.45 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting pale yellow solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C and then N-methoxy-N, 1 -dimethyl- lH-imidazole-5- earboxamide (1.0 g, 6.21 mmol, Intermediate 55: step a) dissolved in DCM (3 mL) was added dropwise. The cold bath was removed and the reaction mixture stirred at room temperature for 48 hours. To the resulting yellow suspension was added water followed by 6 M aqueous HCl to a neutral pH (pH = 6 – 7). The aqueous mixture was extracted with DCM (2 x). The combined DCM extracts were dried over MgS0 , filtered and concentrated under reduced pressure. The product was precipitated with Et20, filtered and dried to provide the title compound as a tan solid.

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; 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.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); 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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Benzo[d]imidazol-2-amine

General procedure: A mixture of aldehyde (1 mmol), 2-aminobenzimidazole (1 mmol), malononitrile (1.1 mmol), RHA-[pmim]HSO4 (10 mg, 0.8 mol %) was heated in an oil bath at 100 C under solvent-free conditions for the appropriate time. After completion of the reaction (monitored by TLC), EtOH was added and the catalyst was separated by filtration. Then water was added, and the precipitated product was separated by filtration in high purity. The spectral data of the new compound are as follows:

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; Shirini, Farhad; Seddighi, Mohadeseh; Goli-Jolodar, Omid; Journal of the Iranian Chemical Society; vol. 13; 11; (2016); p. 2013 – 2018;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 52099-72-6, 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1) added to the three-opening bottle -1 – 1, 3 – dihydro – 2H – (1 – methyl vinyl) benzimidazolone (10 g, 0.06 muM), N, N – dimethyl formamide (50 ml) and NaOH (4.6 g, 0 . 11 muM); dropwise 1, 2 – Dibromoethane (21.5 g, 0 . 11 muM), in the 25 – 30 C under stirring 4 hours; after the reaction is completed, water and ethyl acetate, separating the organic phase; the aqueous phase is extracted with ethyl acetate. The combined organic phase washing, drying, filtering, the concentrated oil of 1, 3 – dihydro -1 – (2 – bromomethyl) -3 – (isopropenyl) – 2H – benzimidazolone 13.9 g (purity 90.8%, yield is 86.2%)

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-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Kelun Pharmaceutical Co., Ltd.; Sichuan Kelun Pharmaceutical Institute Co., Ltd.; Zhao Fulu; Zhang Yong; Cui Hua; Ma Changpeng; Wang Lichun; Wang Jingyi; (16 pag.)CN107235913; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 615-15-6,Some common heterocyclic compound, 615-15-6, name is 2-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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 8; Synthesis of N-4-lH-benzimidazol-2-yl-N-5-(2,4-dimethylphenyl)-2-methyl-lH-imidazole-4,5-dicarboxamide; Synthesis of 2-Methyl-4,5-imidazoledicarboxylic acid; [00177] 2-Methylbenzimidazole (5 g, commercially available from Aldrich) was added to a mixture of concentrated sulfuric acid (55 mL) and water (55 mL) at 90 0C. This was followed by the addition of potassium dichromate (37 g). After 15 – 20 minutes, the mixture was cooled to room temperature and diluted with 1 L of water, which was then kept overnight at room temperature. The resulting solid was filtered off, washed with cold water and air dried to give 4 g of 2-methyl-4,5- imidazoledicarboxylic acid which was used without any further purification. 1H-NMR (DMSO-rfd): delta 2.46 (s, 3H). MS (EI): 171 (MH+).

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-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; EXELIXIS, INC.; WO2008/42282; (2008); A2;,
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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H4ClN3O2

PROCEDURE: 2-chloro-5-nitro-1H-benzo[d]imidazole (200 mg, 1.012 mmol) is slurried with ethanol (6 mL), water (2 mL), and dimethylformamide (0.5 mL). Iron (283 mg, 5.06 mmol), and ammoniumchloride (271 mg, 5.06 mmol) were added and the reaction mixture was heated to reflux for 30 mm. The crude mixture was filtered and the resulting filtrate was concentrated and compound was purified by flash column chromatography (2% CH3OH/CH2C12) afforded the title compound 2-chloro-1H-benzo[d]imidazol-5-amine (150 mg, 0.877 mmol, 87 % yield) as a solid. Proton nuclear magnetic resonance (?1HNMR?) (400 MHz, DMSO-d6): oe 7.14 (d, 1H, J = 8.4 Hz), 6.56 (s, 1H), 6.49 (d, 1H, J = 8.8 Hz), 4.92 (bs, 2H).

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF UTAH; VANKAYALAPATI, Hairprasad; SHARMA, Sunil; SORNA, Venkataswamy; WO2015/31564; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 45676-04-8, 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 45676-04-8 as follows.

trans-diiodo(pyridine)(1-benzyl-3-tert-butylimidazol-2-ylidene)platinum(II)Step 1: 1-benzyl-3-tert-butylimidazolium chlorideA solution of 1-tert-butylimidazole, which was obtained according to A. J. Arduengo (2001) U.S. Pat. No. 6,177,575, (0.31 g; 2.5 mmol) in benzyl chloride (0.3 ml; 2.5 mmol) is stirred at room temperature for 48 h. The volatiles are then evaporated under vacuum. The residue obtained is triturated in ethyl ether and then filtered, thus making it possible to obtain 0.54 g (87%) of 1-benzyl-3-tert-butylimidazolium chloride whose characteristics are the following:1H NMR (300 MHz, CDCl3) delta ppm: 1.73 (s, 9H), 5.71 (s, 2H), 7.15 (m, 1H), 7.25 (m, 1H), 7.38 (m, 3H), 7.52 (m, 2H), 11.41 (s, 1H).

According to the analysis of related databases, 45676-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; US2011/172199; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. Computed Properties of C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

The synthetic route of 6-Aminobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); 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. 83741-35-9, name is 4-Bromo-1H-benzoimidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromo-1H-benzoimidazole

Preparation 47A: 4-Bromo-l- 4-fluorophenyl)-lH-benzo[d]imidazole[00151] A round bottom flask charged with molecular sieves, 4A (189 mg, 1.918 mmol) was flame-dried, then allowed to cool to room temperature. To this vial were added 4-bromo-lH-benzo[d]imidazole (0.378 g, 1.918 mmol), copper (II) acetate (0.523 g, 2.88 mmol), and 4-fluorophenylboronic acid (0.805 g, 5.76 mmol) followed by CH2CI2 (Volume: 9.59 ml) and triethylamine (0.695 ml, 4.99 mmol). The heterogeneous green reaction was stirred at room temperature. After 19 h, the reaction mixture was filtered through a disposable filter funnel and the filter cake rinsed with CH2CI2. The filtrate was concentrated to afford a green residue. The crude material was dissolved in a minimal amount of CH2CI2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 0-100% EtOAc in hexanes over 25 min, tr = 13 min) gave 4-bromo-l-(4-fluorophenyl)-lH- benzo[d]imidazole (158 mg, 0.299 mmol, 15.56% yield) as a white solid. LC-MS showed by-product was present. The material was re-dissolved in a minimal amount of CH2CI2 (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (12 g column, 30 mL/min, 0-25% EtOAc in hexanes over 13 min, tr = 10 min) gave Preparation 47A (158 mg, 0.299 mmol, 15.56% yield) as a white solid. LC-MS showed the product was 55% pure. The mixture was further purified by MPLC (40 g column, 36 mL/min, 30-60% EtOAc in hexanes) to afford Preparation 47A as a white solid (51 mg, 9.1%). MS (ESI) : m/z = 291.0 [M+H]+. HPLC Peak tr = 1.70 minutes was product. HPLC conditions: Column:Luna CI 8 4.6x30mm 3u A: 10:90 H20:ACN NH4OAc/B: 10:90 H20:ACN NH4OAc; 0%-95%B in 2 min; 4mL/min flow.

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 83741-35-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HUANG, Audris; WO2012/44537; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem