Tag: M.W=0-100

Synthetic Route of 288-32-4, 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.

To a solution of 1H-Imidazole (5 g, 73.5 mmol) in THF was added sodium hydride (1.8 g, 45 mmol) and stirred at room temperature for 0.5 hour before addition of then bromo-acetonitrile (8.8 g, 73.9 mmol) and stirring at room temperature for 2 hours. The reaction was quenched via the addition of water (50 mL) and saturated ammonium chloride (50 mL) solution and the mixture was extracted with ethyl acetate (100 mL*3). The combined organics layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude residue was purified on silica gel (petroleum ether:ethyl acetate=10:1) to afford 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59%) as a yellow oil. LRMS m/z: 108 [M+H+].

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:
Patent; Albrecht, Brian K.; Bellon, Steven F.; Gehling, Victor S.; Harmange, Jean-Christophe; LeBlanc, Yves; Liang, Jun; Magnuson, Steven; Tsui, Vicki; Zhang, Birong; US2015/65522; (2015); 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

Application of 1072-62-4, The chemical industry reduces the impact on the environment during synthesis 1072-62-4, name is 2-Ethyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: The synthetic route is shown in Scheme 2. For example, to a stirred solution of compound 2 (506mg, 83 1 mmol) in 30 mL acetonitrile were added anhydrous K2CO3 (275 mg, 2mmol) and imidazole (204mg, 3mmol) at 25. Then the mixture was stirred at 25 for 24 h. The reaction mixture was filtered, and the 85 filtrate was evaporated under reduced pressure. The residue was treated with water (50 mL) and extracted 86 with dichloromethane (4¡Á30 mL). The organic layer was combined, dried with anhydrous Na2SO4, and 87 concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography 88 with chloroform/methanol (5:1) as eluent to give compounds 6-24 as solid.compound 6. 4?-(3-Imidazole-propoxy)-arctigenin. Yeild 83.33%.

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

Reference:
Article; Hu, Yang; Liu, Lei; Li, Boyang; Shen, Yufeng; Wang, Gao-Xue; Zhu, Bin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 183 – 194;,
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. 10111-08-7, name is Imidazole-2-carboxaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: Imidazole-2-carboxaldehyde

General Procedure E; (according literature reference Bioorg. Med. Chem. 2005, 13 , 363-386) [00126] l-ethyl-lH-imidazole-2-carbaldehyde[00127] To a heterogeneous mixture of imidazole-2-carboxaldehyde (500 mg, 5.20 mmol, 1 eq) and potassium carbonate (863 mg, 6.24 mmol, 1.2 eq) in N,N-dimethylformamide (5.0 mL) was added iodoethane (0.499 mL, 6.24 mmol, 1.2 eq). The reaction mixture was heated to 50 0C for 5 hours then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated and washed successively with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give crude l-ethyl-lH-imidazole-2-carbaldehyde as a mixture with N,N- dimethylformamide (-1: 1) which was used without further purification. [00128]

The synthetic route of 10111-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2009/67233; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 930-62-1,Some common heterocyclic compound, 930-62-1, name is 2,4-Dimethylimidazole, molecular formula is C5H8N2, 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.

A solution of 2,4-dimethylimidazole (8-40 g; 87.38 mmol) in dry DMF (250 mL) was treated with potassium tert-butoxide (9.806 g; 87.38 mmol). The mixture was stirred at ambient temperature until homogenous. tert-Butyl bromoacetate (15.29 mL; 104.9 mmol) was added dropwise. The solution was stirred for 15 min, then diluted with isopropyl acetate (400 mL) and washed with pH7 phosphate buffer (3¡Á250 mL). The organic was dried over MgSO4, filtered and evaporated to an oil. The crude product (consisting of the two title compounds) was chromatographed over silica gel (0% to 10% MeOH/CH2Cl2; linear gradient). All fractions containing the two products were combined. The residue was rechromatographed on Chiralcel OD stationary phase (Daicel Chemical Industries Ltd., Chiralcel Technologies Inc.; 10% ethanol/heptane; lambda=220 nM). The more mobile 2,5 isomer and less mobile 2,4 isomer were obtained.500 MHz 1H NMR (CDCl3): (2,4 isomer) delta 6.49 (s, 1H), 4.39 (s, 2H), 2.24 (s, 3H), 2.17 (s, 3H), 1.42 (s, 9H); (2,5 isomer) delta 6.67 (s, 1H), 4.41 (s, 2H), 2.35 (s, 3H), 2.15 (s, 3H), 1.48 (s, 9H).

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10111-08-7, name is Imidazole-2-carboxaldehyde, 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 10111-08-7, COA of Formula: C4H4N2O

To a mixture of sodium hydride (500 mg, 12.5 mmol) in N,N-dimethylformamide (10 mL) was added lH-imidazole-2-carbaldehyde (1.00 g, 10.4 mmol). The reaction mixture was stirred at rt for 1.5 hrs. Then 2-(chloromethoxy)ethyl-trimethyl-silane (2.08 g, 12.5 mmol) was added at 0 C. The reaction mixture was stirred at rt for 16 hrs. On completion, the mixture was quenched by water (50 mL) and extracted with ethyl acetate (3 X 100 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (petroleum ether: ethyl acetate = 5: 1) to give the title compound. LH MR (400 MHz, CDC13) delta = 9.85 (s, 1H), 7.39 (s, 1H), 7.35 (s, 1H), 5.80 (s, 2H), 3.59 (t, J = 8.4 Hz, 2H), 0.92 – 1.00 (m, 2H), 0.003 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Imidazole-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

l,4-Diazabicyclo[2.2.2]octane (21 g, 187.33 mmol) and dimethyl sulfamoyl chloride (18.4 mL, 171.72 mmol) were added to a stirred suspension of lH-imidazole-4- carbaldehyde (15 g, 156.11 mmol) in acetonitrile (300 mL) at 0 C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was concentrated in vacuo and the residue was diluted with water and extracted withEtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 60/40). The desired fractions were collected and concentrated in vacuo to yield 4-formyl-N,N-dimethyl-lH-imidazole-l -sulfonamide (27.2 g, 86 % yield) as a cream solid.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1H-Imidazole

(a) N-Benzylimidazole To a solution of 24 g (1 mol) of sodium hydride in 500 ml of N,N-dimethylformamide, there was added, drop-by-drop, a solution of 68 g (1 mol) of imidazole in 150 ml of N,N-dimethylformamide. The medium was stirred for 2 hours and then 126.6 g (1 mol) of benzyl chloride were added. The solvent was eliminated and the residue was taken up with ethyl acetate and washed with water. The organic phase was dried and concentrated to provide an oil which crystallized when cold. In this manner, N-benzylimidazole was obtained in a yield of 70%.

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; Sanofi; US5017579; (1991); 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. 1072-63-5, name is 1-Vinyl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 1-Vinyl-1H-imidazole

(1) Add an appropriate amount of acetonitrile as a solvent to dissolve N-vinylimidazole in a three-necked flask for later use, weigh and configure it as Br (CH2) 6Br:N-vinylimidazole = 1: 2 (molar ratio) mixed product is ready for use; N-vinylimidazole acetonitrile solution is circulated at 82 C under reflux conditions.The above mixture was added dropwise to a three-necked flask and continuously stirred for 24 h.After the reaction, a pale yellow liquid was obtained, and the residual solvent was evaporated under reduced pressure.It was washed several times with ethyl acetate and acetone successively; the product was dried under vacuum to obtain (ViIm) 2C6 (Br) 2.

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; Chengdu Mingdian Shijia Biological Technology Co., Ltd.; Song Hang; (15 pag.)CN110590675; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 616-47-7, These common heterocyclic compound, 616-47-7, name is 1-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.

A literature procedure for the synthesis of the title compound was adopted. 2 A solution of N-methyl-1H-imidazole (280 muL, 290 mg, 3.50 mmol) in anhydrous THF (7 mL) was cooled to -78C and n-BuLi (2.5 M in hexanes, 2.2 mL, 3.60 mmol) was added dropwise by syringe under stirring. The resulting yellow solution was stirred for 30 minutes at -78C where upon chlorotrimethylsilane (465 muL, 399 mg, 3.67 mmol) was added dropwise by syringe; after the addition the resulting reaction mixture was allowed to return to room temperature and the stirring was continued for 1 h. The reaction was then cooled back to -78C, ethylchloroformiate (350 muL, 398 mg, 3.67 mmol) was added and the resulting mixture was allowed to warm up to room temperature and further stirred for 1h. The reaction was quenched with water (1 mL) and the solvents were evaporated under reduced pressure. The obtained crude product was dissolved in dichloromethane (100 mL), washed with water (3 x25 mL) and brine (1 x 25 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with EtOAc as eluent, the chromatographic fractions containing the required compound were collected and concentrated under reduced pressure, affording the title compound 1f as a colorless liquid(152 mg, 37%).

Statistics shows that 1-Methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 616-47-7.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem