Month: June 2021

Application of 4238-71-5, 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. 4238-71-5, name is 1-Benzyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cooled (-500C) suspension of 1 -benzyl- lH-imidazole (1,58 g, 10.0 mmol) in anhydrous diethyl ether (50 mL) under nitrogen was added H-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at – 500C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL), acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of this precipitate gave a white solid which was suspended in methanol, treated with IiV HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded the HCl salt of Cap- 136 as a white solid (817 mg, 40%). 1H NMR (300 MHz, DMSO-d6) delta 7.94 (d, J= 1.5 Hz, IH), 7.71 (d, J- 1.5 Hz, IH), 7.50-7.31 (m, 5H), 5.77 (s, 2H); Rt = 0.51 min (Cond. MS-W5); 95% homogenity index; LRMS: Anal. CaIc. for [M+H]+ C11H12N2O2: 203.08; found: 203.11.

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-Benzyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LOPEZ, Omar D.; CHEN, Qi; BELEMA, Makonen; WO2010/138368; (2010); 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 150058-27-8 as follows. category: imidazoles-derivatives

To the crude CBME (20 g, 1 eq) obtained in the above-mentioned (3) were added methanol:water [(1:1) (160 mL)] and sodium hydroxide (4.4 g, 3 eq) at 25°C – 30°C, and the reaction mixture was stirred at 75°C – 80°C for 4 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of CBME was confirmed. The reaction mixture was cooled to 25°C – 30°C, and the organic solvent was evaporated under reduced pressure at 40°C – 45°C. To the concentrated residue was added water (200 mL, 10 vol), and the aqueous layer was washed with t-butyl methyl ether (100 mL, 2×5 vol). The aqueous layer was adjusted to pH 5.5 – 6.5 by adding acetic acid (6 mL, 0.3 vol), the obtained slurry was stirred at 25°C-30°C for 1 hr, and the precipitated solid was filtered. The solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and further dried at 50°C – 55°C for 4 hr to give crude CBCA (16 g). [0327] To the obtained crude CBCA (16 g) were added ethyl acetate (160 mL, 10 vol) and dicyclohexylamine (DCHA) (8.2 g, 1.5 eq), and the mixture was stirred at 25°C – 30°C for 2 hr. The precipitated solid was filtered, washed with ethyl acetate (80 mL, 5 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a DCHA salt (16 g) of CBCA. To the salt was added isopropyl alcohol (192 mL, 12 vol) at 25°C – 30°C, and the salt was dissolved by heating to 75°C – 85°C, and the mixture was stirred for 15 min. Thereafter, the reaction mixture was cooled to 25°C – 30°C, and stirred at the same temperature for 2 hr. The precipitated solid was filtered, washed with isopropyl alcohol (32 mL, 2 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a pure DCHA salt (13 g) of CBCA. To this salt was added 25percent aqueous sodium hydroxide solution (120 mL, 10 vol) at 25°C – 30°C, and the mixture was stirred for 15 min, adjusted to pH 5.5 – 6.5 by adding acetic acid (5.8 mL, 0.48 vol), and extracted with methylene chloride (120 mL, 2×5 vol). The extract was combined with the organic layer, and the mixture was washed with water (120 mL, 2×5 vol) and further with saturated brine (60 mL, 5 vol). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure at 40°C – 45°C to give CBCA (9 g, 47percent from BCL).

According to the analysis of related databases, 150058-27-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, A new synthetic method of this compound is introduced below., Safety of 2-(1H-Imidazol-1-yl)acetic acid

Step (2): Compound 76 + Compound 77 ? Compound 78; To Compound 76 (126 mg, 1.0 mmol) was added dichloromethane (4 ml), Compound 77 (365 mg, 1.00 mmol), and WSCD·HCl (249 mg, 1.30 mmol), followed by stirring at 0C for 1 hour and then at room temperature for 1 hour. Dimethylformamide (2 ml) was added, subsequently stirring for 1 hour, and then concentrated in vacuo to evaporate dichloromethane. Dimethylformamide (2 ml) was added, and then allowed to stand for 3 days. Dichloromethane and water were then added. The organic layer was washed with water, washed with saturated brine, dried over magnesium sulfate, and then filtrated to yield Compound 78 (390 mg, 58% yield, 70% potency).

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; Shionogi&Co., Ltd.; EP2341053; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1450-93-7, These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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.

EXAMPLE 1 5-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,2-a]pyrimidine A mixture of 2.64 g of 2-aminoimidazole hemisulfate, 1.64 g of anhydrous sodium acetate, 4.86 g of 3-dimethylamino-3′-(trifluoromethyl)-acrylophenone and 50 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo to yield a crude solid. The solid was dissolved in dichloromethane and this solution was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over powdered anhydrous sodium sulfate. This solution was passed through a short column of a hydrous magnesium silicate and the effluent was refluxed on a steam bath with the gradual addition of hexane until turbidity was noted. After cooling the desired compound was collected by filtration and gave 1.20 g of pale yellow crystals, m.p. 160-163 C.

Statistics shows that 1H-imidazol-2-amine sulfate(2:1) is playing an increasingly important role. we look forward to future research findings about 1450-93-7.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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 60-56-0, SDS of cas: 60-56-0

2-mercapto-1-methylimidazole (400 mg, 3.5 mmol) was mixed with K2CO3 (968 mg, 7 mmol) in N, N-dimethylformamide (N, N-dimethylformamide ) (7 mL), followed by addition of di-tert-butyl dicarbonate (1.1 mL, 5.2 mmol). The resulting mixture was then stirred at 60 C for 30 minutes in a nitrogen atmosphere, followed by partitioning with ethyl acetate (40 mL) and water (20 mL). The ethyl acetate layer was then collected and washed with brine (brine), dried over anhydrous MgSO4, and then concentrated under vacuum. Thereafter, the resulting residue was purified by silica gel column chromatography to give a compound (665 mg, yield 89%) as a pale yellow solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; HUNGKUANG UNIVERSITY; Chan, JinFeng; Chen, MingRen; LAI, SHITING; GUO, YIQIN; (36 pag.)TW2016/7932; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 24134-09-6, name is 5-Bromo-1,2-dimethyl-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 24134-09-6, Safety of 5-Bromo-1,2-dimethyl-1H-imidazole

A solution of n-BuLi (2.66 M in hexane, 19.5 mL, 51.9 mmol) in THF (100 mL) was stirred under argon at ?-70 C. while a solution of 5-bromo-1,2-dimethyl-1H-imidazole (9.13 g, 52.2 mmol) in THF [60 mL; containing 3 A molecular sieves (18 g)] was added dropwise over 8 minutes via cannula. After stirring for another 4 minutes at ?-70 C., neat ethyl methoxy(methyl)carbamate (2.96 mL, 22.7 mmol) was added dropwise over 3 minutes. This mixture was stirred at ?-70 C. for an additional 5 minutes, and the cold bath was then removed and the slurry was allowed to warm to room temperature with stirring for 1.5 hours. The reaction was then quenched with 5 M aqueous NH4Cl (15 mL), dried (Na2SO4), filtered, and concentrated under high vacuum at 80 C. The resulting orange gummy residue was triturated with hot heptane (?40 mL) and the decanted supernatant was allowed to crystallize to provide impure title compound. This was recrystallized from toluene (?30 mL) to provide, after washing the off-white crystalline filter cake with toluene (2*?3 mL), the title compound as an off-white crystalline solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-dimethyl-1H-imidazole, and friends who are interested can also refer to it.

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; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 4 3-Acetyl-6-chloro-4-phenylquinolin-2(1H)-one (100 mg, 0.31 mmol) was added to a solution of NaOH (18 mg, 0.44 mmol) in EtOH (20 mL) and H2O (1 mL). The mixture was stirred at room temperature for 30 mins. Then 1-methyl-1H-benzo[d]imidazole-2-carbaldehyde (60 mg, 0.37 mmol) was added and the mixture was stirred at 35° C. overnight. The mixture was concentrated to dryness and the residue was diluted with EA (10 mL). The mixture was washed with water (10 mL), brine (10 mL) and dried over anhydrous Na2SO4. The mixture was concentrated to give a crude solid, which was purified by prep-HPLC to give 6-chloro-3-[3-(1-methyl-1H-benzoimidazol-2-yl)-acryloyl]-4-phenyl-1H-quinolin-2-one (50 mg, yield: 37percent) as a yellow solid. 1HNMR (400 MHz, DMSO-d6): delta=12.41 (brs, 1H), 7.69-7.02 (m, 13H), 7.01 (d, J=3.2 Hz, 1H), 3.88 (s, 3H). MS: m/z 440.1 (M+H+).

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

Reference:
Patent; Sanford-Burnham Medical Research Institute; The Royal Institution for the Advancement of Learning / McGill University; The Government of the United States of America as Represented by the Secretary of the Department of; RONAI, Ze’ev; PINKERTON, Anthony B.; FENG, Yongmei; TOPISIROVIC, Ivan; BROWN, Kevin; HASSIG, Christian A.; (155 pag.)US2018/44324; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

All reagents and solvents used to obtain (1) and (2) were of p.a.quality, and used without any previous purification process. A suspensionin continuous stirring of H3IDC (0.156 g, 1.00 mmol), 2,2-bipyridine (0.078 g, 0.50 mmol) and 70 lL of dipropylamine(DPA) in 10 mL of acetonitrile (MeCN), was mixed with a solutionof Cu(NO3)23H2O (0.121 g, 0.50 mmol) in 10 mL of H2O/MeCN 1:1. The deep blue slurry solution was filtered and the supernatantwas kept at room temperature for 1 day providing blue needle-likecrystals, which can be isolated by filtration. As the crystals turnedopaque under air suggesting a loss of crystallinity, for X-ray experimentsthe crystals were picked out and immediately glued toavoid any solvent loss. MW: 565.9 g/mol. Yield of 82%, based oncopper salt.

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-4,5-dicarboxylic acid, its application will become more common.

Reference:
Article; Cruz, Carlos; Spodine, Evgenia; Venegas-Yazigi, Diego; Paredes-Garcia, Veronica; Polyhedron; vol. 136; (2017); p. 117 – 124;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15788-16-6, The chemical industry reduces the impact on the environment during synthesis 15788-16-6, name is 1H-Benzo[d]imidazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

Example 1 N2-((lH-Benzo[d]imidazol-5-yl)methyl)-N’-(5-cyclopropyl-lH-pyrazol-3-yl)pyrimidine-2,4- diamine (I- 13) step 1 : Thionyl chloride (10 mL) was added dropwise to a solution of lH-benzo[d]imidazole-5-carboxylic acid (4.8 g, 30 mmol) in MeOH (150 mL) cooled to 0 C. The reaction mixture was heated at reflux for 18 h, and then solvent (about 2/3) was concentrated under reduced pressure. After cooling, a yellow solid was precipitated from the solution and was filtered to afford 4 g (90%) of methyl lH-benzo[d]imidazole- 5-carboxylate (20): MS (ESI) m/z = 111 [M+l]+.

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, 1H-Benzo[d]imidazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

Cetyl chloride (1.26 mL, 17.4 mmol) was slowly added to a stirred solution of the imidazole 1.0g, 14.5 mmol in anhydrous tetrahydrofuran 20 mL under ice, under N2. The suspension wasstirred for 30 minutes and triethylamine (2.4 mL, 17.4 mmol) was added. The reaction mixture was stirred at 0 °C for 12 hours. Then the reaction mixture was filtered, and the solvent was evaporated under reduced pressure to give 1-acetylimidazole 1.53g, 13.9mmol, 94.5 as a white solid.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tian, Qingqiang; Gan, Zongjie; Wang, Xuetong; Li, Dan; Luo, Wen; Wang, Huajun; Dai, Zeshu; Yuan, Jianyong; Molecules; vol. 23; 9; (2018);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem