Category: 822-36-6

These common heterocyclic compound, 822-36-6, name is 4-Methyl-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. Application In Synthesis of 4-Methyl-1H-imidazole

In a pressure tube with one end sealed, add 190 mg CuI (1 mmol), 1.64 g 4-methyl-1H-imidazole (20 mmol), 3.25 g Cs2CO3 (10 mmol), and after Nitrogen replacement, add 2.40 g 3-bromo-5-(trifluoromethyl)aniline (10 mmol), 350 mg 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (2 mmol) and 30 mL DMF was added into a flask. The mixture was stirred at 110 C. for 18 h under sealing. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by column chromatography to afford 2.19 g desired product (91%). 1H NMR (400 MHz, d-DMSO), delta 8.06 (s, 1H), 7.35 (s, 1H), 6.97 (s, 1H), 6.93 (s, 1H), 6.81 (s, 1H), 5.87 (br, 2H), 2.15 (s, 3H). MS (ESI), m/z: 242 (M++H+).

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

Reference:
Patent; Guangzzhou Institute of Biomedicine and Health, Chineses Academy of Sciences; Ding, Ke; Wang, Deping; Pei, Duanqing; Zhang, Zhang; Shen, Mengjie; Luo, Kun; Feng, Yubing; US2013/196985; (2013); A1;,
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

Application of 822-36-6, 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. 822-36-6, name is 4-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 30; [229] Preparation of 3-(4-methyl-imidazol- 1 – yl)-5-trifluoromethyl-phenylamine; [230] 3-amino-5-bromo-benzotrifluoride (17.1g,71.24mmol), 4-methylimidazole (17.6g,213.72mmol), potassium carbonate (9.8g, 71.24mmol), cupper (1. Ig, 17.81mmol), and cupper iode (II) (3.4g, 17.81mmol) were added to N,N-dimethylacetamide (100ml) at room temperature, and mixed therewith at 140~150C for 16 hr. After the reaction was completed, the temperature of the reaction vessel was cooled to RT. Then, ethyl acetate (200ml) was added thereto and mixed therewith for 30 min. The reaction mixture was filtered with Celite, and an organic layer of the filtered solution was washed with water, dried with magnesium sulfate, distilled under vacuum, and washed with n- hexane to give the titled compound as pale white solid.[231] 1H-NMR (CDCl3 delta)= 2.28 (s,3H), 4.04 (br,2H), 6.79 (s,lH), 6.83 (s,lH), 6.92(s,lH), 7.00 (s,lH), 7.77 (s.lH)

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

Reference:
Patent; IL-YANG PHARM. CO., LTD.; WO2007/18325; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 822-36-6, name is 4-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 822-36-6, Recommanded Product: 822-36-6

Example 18: Preparation of 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl benzoic acid : In 3 lit four necked round bottom flask equipped with mechanical stirrer, thermometer, reflux condenser and an addition funnel, 3-fluoro-5-(trifluoromethyl)benzoic acid (80 g), 4-methylimidazole (47.2 g) and dimethylacetamide (400 ml) was added, heated to 80-85C and stirred for 12 hrs at the same temperature. The reaction mass was cooled to room temperature, diluted with water (500 ml) and extracted with ethyl acetate (1000 ml). The solvent from organic layer was distilled off under vacuum and th obtained residue was titrated with water to get the title compound. Yield: 63 g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; LAURUS LABS LTD; BOLLU, Ravindra Babu; BANDLAMUDI, Veera Narayana; KUDIRILLA, Vivek Kumar; VEMULA, Rambabu; VASIREDDI, Uma Maheswer Rao; (36 pag.)WO2019/130254; (2019); 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. 822-36-6, name is 4-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C4H6N2

A. 4-Methylimidazole (10 g, 0.12 moles), was cooled in a flask, and fuming nitric acid (11 ml, 0.24 moles) was added dropwise. This was followed by the addition of sulfuric acid (11 ml). The reaction was then heated with stirring at 100 C. for 21/2 hours. The cooled reaction mixture was then added to 500 ml of ice water, and the precipitate was filtered off. The filtrate was neutralized with ammonium hydroxide, and filtered again. The combined precipitates were then recrystallized from water to give 6.35 g of 4-methyl-5-nitroimidazole.

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; Merck & Co., Inc.; US4678799; (1987); 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. 822-36-6, name is 4-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Formula: C4H6N2

A suspension of 3- bromo-5-(trifiuoromethyl)aniline (4.8 g, 20 mmol), 4-methylimidazole (1.97 g, 24 mmol), potassium carbonate (3.04 g, 22 mmol), CuI (0.57 g, 3 mmol), and 8-hydroxyquinoline (0.44 g, 3 mmol,) in dry DMSO (20 mL) in a pressure tube was degassed by bubbling N2 into the suspension for 10 minutes while stirring. The tube was sealed tightly. The mixture was heated at 120 0C (oil bath temperature) for 15 h. The mixture was cooled down to 45- 50 0C and 14% aq. NH4OH (20 mL) was added. The mixture was maintained at this temperature for 1 h. After cooling to rt, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were passed through a short silica gel column to remove most of green/blue Cu salts. The filtrate was dried over sodium sulfate and concentrated on a rotavap. The crude product was recrystallized from EtOAc/hexanes, giving pure pale yellow needles. The mother liquor was concentrated and the residue was purified on silica gel column (5% methanol/methylene chloride), yielding a second crop as pale yellow needles.

The synthetic route of 822-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; WO2007/75869; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 822-36-6,Some common heterocyclic compound, 822-36-6, name is 4-Methyl-1H-imidazole, molecular formula is C4H6N2, 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 9 5-(4-Methyl-1 H-imidazol-1 -yl)-3-trifluoromethyl-phenylamine (I) EPO To a single neck flask fitted with a condenser are added CuI (89.5 mg, 0.47 mmol), cyclohexanediamine (107.3 mg, 0.94 mmol) and diglyme (10 ml_). The mixture is stirred for 10 minutes at ambient temperature. To the purple heterogeneous mixture, 3-bromo-5- trifluoromethyl-phenylamine (XVI) (1.13 g, 4.7 mmol), 4-methyl-1 /-/-imidazole (0.77 g, 9.4 mmol) and Cs2CO3 (1.53 g, 4.7 mmol) are added. The mixture is heated at 1500C and stirred for an additional 24 hours. The mixture is cooled to 250C and purified by column chromatography (silica gel; EtOAc/MeOH 95:5) to afford (I) as the major product (840 mg).

The synthetic route of 822-36-6 has been constantly updated, and we look forward to future research findings.

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. 822-36-6, name is 4-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 822-36-6

4-Methylimidazole (249 mg, 3.03 mmol), 4-fluoro-3-methoxybenzonitrile (417 mg, 2.76 mmol), and cesium carbonate (1.89 g, 5.80 mmol) were placed in a reaction vessel in a nitrogen gas atmosphere, N,N-dimethylformamide (5.0 mL) was added to the vessel and the resultant mixture was stirred at room temperature for 96 hours. To the reaction mixture were successively added water (2 mL) and ethyl acetate (6 mL) to perform an extraction, and the aqueous layer was separated and then, the organic layer was washed with water (5 mL). To the organic layer were added ethyl acetate (5 mL) and water (5 mL) to perform an extraction, and the aqueous layer was separated and then, the organic layer was washed with water (5 mL) and concentrated under a reduced pressure to obtain 499 mg of a crude product. To the crude product was added tert-butyl methyl ether (2.5 mL) to obtain a suspension, and the solids collected by filtration of the suspension were washed with tert-butyl methyl ether/heptane (2.5 ml; 1 :3) three times to obtain 431 mg of a crude product. To the obtained crude product was added tert-butyl methyl ether (4.3 mL) in a nitrogen gas atmosphere, and the resultant mixture was stirred at 50C for 30 minutes and then naturally cooled to room temperature, and the solids collected by filtration were washed with tert-butyl methyl ether/heptane (2.1 mL; 1 :3) twice and dried under a reduced pressure to obtain 310 mg of a title compound. Yield: 53%.

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.

These common heterocyclic compound, 822-36-6, name is 4-Methyl-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. Application In Synthesis of 4-Methyl-1H-imidazole

To the solution of Bromo-5-trifluoromethyl-phenylamine (500 mg, 2.1 mmol, 1.0 eq), 4-methyl-1H-imidazole (20.5 mg, 2.5 mmol, 1.2 eq), cuprous iodide (0.14 eq) and 8-hydroxyquinoline (44 mg, 0.3 mmol, 0.14 eq) in 3 mL dimethylsulfoxide was purged with nitrogen 3 times and the solution was heated to 120 C., the mixture was diluted with water after completion of the reaction. Then the organic layer was washed successively with dilute aqueous ammonia solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was isolated by column chromatography to give the title product as a yellow solid (392 mg, 77.3% yield). 1H NMR (400 MHz, CDCl3) delta7.73 (s, 1H), 6.98 (s, 1H), 6.92 (s, 1H), 6.83 (s, 1H), 6.77 (s, 1H), 4.14 (s, 2H), 2.27 (s, 3H). MS m/z (ESI): 242.1 [M+H].

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

Reference:
Patent; Si Chuan University; Yang, Shengyong; Wei, Yuquan; (168 pag.)US2017/305920; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 822-36-6,Some common heterocyclic compound, 822-36-6, name is 4-Methyl-1H-imidazole, molecular formula is C4H6N2, 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.

4-Fluoro-3-methoxybenzonitrile (98.2 g, 0.65 mol) was combined with 4-methyl-1 /-/- imidazole (53.4 g, 0.65 mol) and anhydrous potassium carbonate (138.2 g, 1 mol, 1.54 eq) in dimethylformamide (650 ml_), and the reaction mixture was stirred for 16 hours at 135-140 0C (internal temperature). The mixture was cooled to room temperature and filtered; the salts were washed with dichloromethane (3 x 30 ml_). The combined filtrates were evaporated in vacuo to afford a brown semisolid, which was suspended in water (500 ml_) and left to stand at 5 0C for 24 hours. The mixture was filtered, and the solid was washed with ice water (2 x 50 ml_), then dried in vacuo to afford a yellow solid (105.5 g). Crystallization from methanol (106 ml_) provided purified product (66.3 g) as yellowish crystals. These were boiled with acetone (100 ml_) for 5 minutes and the mixture was left to cool overnight. The mixture was filtered, and the crystals were washed with acetone (2 x 10 ml_) to afford the title compound as a white solid. Yield: 54.6 g, 0.256 mmol, 39%. 1H NMR (400 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.94 (s, 3H), 6.97 (m, 1 H), 7.30 (m, 1 H), 7.37 (m, 2H), 7.79 (d, J=1.4 Hz, 1 H).

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

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