Category: 616-47-7

Related Products 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.

1-methylimidazole (1 mmol, 82.1 mg),Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction. The mixture is poured into water and extracted with dichloromethane. The organic phase is collected, dried, and the dichloromethane is removed by rotary evaporation.Crude product. The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (volume ratio = 10:1) to obtain 2-Bromo-1-methylimidazole (red-brown liquid, 101.4 mg, yield 63%).

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); 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. 616-47-7, name is 1-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 616-47-7

1-methylimidazole (1 mmol, 82.1 mg),Perfluoro iodobutane (3.1 mmol, 1072 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (2.2 mmol, 246.9 mg) was addedAnd 5mL of toluene, stirring at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).The product 1 was obtained: 2-iodo-1-methylimidazole (white solid, 72 mg, 35%).Product 2: 2,5-diiodo-1-methylimidazole (white solid, 210 mg, 63%)

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; Liaoning University; Liang Fushun; Liu Xia; Han Zhengbo; Su Zhongmin; (10 pag.)CN107501023; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 616-47-7,Some common heterocyclic compound, 616-47-7, name is 1-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.

Triethylamine (3.40 mL, 24.4 mmol) and Ethyl chloroformate (2.34 mL, 24.4 mmol) were added at 0 C. to an acetonitrile (4.0 mL) solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol), and the reaction solution was stirred at room temperature for 16 hours. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate), thereby obtaining ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80%) as a white solid.1H-NMR (400 MHz, CDCl3) delta: 1.42 (3H, t, J=7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J=7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m)ESI-MS: m/z=155 (M+H)+

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toray Industries, Inc.; Takahashi, Hirozumi; Baba, Yoko; Morita, Yasuhiro; Iseki, Katsuhiko; Izumimoto, Naoki; (19 pag.)US2020/172507; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 616-47-7, 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. 616-47-7, name is 1-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1-methyl-1H-imidazole (200 g, 2.44 mol) in anhydrous THF (2 L) was added dropwise n-BuLi (2.5M, 1.07 L, 2.68 mol) at -78 C with stirring over 2 h. Then perchloroethane (800 g, 0.845 mol) in dry THF (1L) was added dropwise to above solution over 1h at the same temperature. After the starting material was consumed, the mixture was poured into saturated ammonium hydrochloride, extracted with ethyl acetate (800 mL x 3), washed with brine, the organic phase was dried and concentrated to give crude product which was purified by column chromatography on silca gel (PE/ EtOAc = 20:1~5:1) to give the title compound (170 g, 60%) as a yellow oil.

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

Reference:
Article; Chen, Yantao; Goldberg, Frederick W.; Xiong, Jian; Wang, Shujun; Synthesis; vol. 47; 5; (2015); p. 679 – 691;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 616-47-7, A common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-imidazole, molecular formula is C4H6N2, 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.

Triethyl amine (5OmL) is added to a solution of methyl imidazol (16.3g, 199mmol) in acetonitrile (10OmL), then it is cooled to -300C. A solution of ethyl chloroformate (3ImL, 328mmol) in acetonitrile (5OmL) is added slowly keeping the temperature bellow 100C. The reaction mixture is concentrated and diluted in water and extracted with chloroform, dried with MgSO4 anh, filtered and evaporated. Recrystallisation from ether yields l-Methyl-lH-imidazole-2- carboxylic acid ethyl ester as an orange oil (15.5g, 51%).

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; BIOFOCUS DPI LIMITED; WO2009/24585; (2009); A2;,
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. 616-47-7, name is 1-Methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H6N2

General procedure: N-methyl imidazole (17.53 ml, 0.22 mol) and 1,4-butane sultone (20.5 ml, 0.20mol) were dissolved in toluene (60 ml) and stirred for 8h at 60ºC under nitrogen atmosphere. The white zwitter ion solid so formed was filtered and washed repeatedly with diethyl ether (3 × 40 ml) to remove non-ionic residues.The resulting solid (MIM-BS) was dried in vacuum for 8h. The MIM-BS (10.0 gm,0.0463 mol) was dissolved in water (2 ml) with constant stirring.Methanesulfonic acid (3 ml, 0.0463 mol) was taken in water (1 ml) and added to the reaction contents dropwise. The mixture was stirred for 6h at 85ºC. After completion of the reaction, water was removed and contents were dried for 24h under reduced pressure. The resulting colorless viscous liquid was stored in dry box for further use.

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 616-47-7.

Reference:
Article; Garg, Bhaskar; Ling, Yong-Chien; Tetrahedron Letters; vol. 53; 42; (2012); p. 5674 – 5677;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 616-47-7, 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 616-47-7 as follows.

To a solution of N-methylimidazole (1.64 g, 19.97 mmol) and sodium acetate (25 g, 300 mmol) in acetic acid (180 mL) at room temperature was added bromine (9.6 g, 60.07 mmol) dropwise as a solution in 20 mL acetic acid. The resulting mixture was stirred for 2.5 h at room temperature. Acetic acid was removed in vacuo, the residue was suspended in 500 mL water and stirred at room temperature for 10 minutes. The resultant precipitate was filtered, washed with water and dried under high vacuum to give 2,4,5-tribromo-l-methyl- lH-imidazole (1.82 g, 29% – some product remained in the mother liquor) as a light yellow powder. Used without further characterization. To a suspension of the tribromide (1.82 g, 5.71 mmol) in 45 mL water was added sodium sulfite (13 g, 103 mmol) and the resulting mixture was stirred at rapid reflux for 24 h. After cooling to room temperature, organics were extracted with ether (3 chi 75 mL), dried over magnesium sulfate, filtered and concentrated to give 1.61 g of a mixture of tri-, di- and monobromoimidazoles. This mixture was re-subjected to the reduction conditions (same quantity of sodium sulfite) using 15 mL of 3: 1 water/acetic acid as solvent and heating in a sealed vessel at 130 C for 60 h. After cooling to room temperature, the pH of the reaction mixture was adjusted to 9-10 by addition of 2 N sodium hydroxide. Organics were extracted with ether (3 chi 50 mL), dried over magnesium sulfate, filtered and concentrated to give crude 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 62%). Used without further characterization.. 4-Butyl-l -methyl- lH-imidazole (95 mg, 22 %) was synthesized as in Example 3.1 using 4-bromo-l -methyl- lH-imidazole (571 mg, ca. 3.53 mmol) in place of 5-bromo-2- formylfuran and propylboronic acid (372 mg, 4.24 mmol) in place of hexylboronic acid. Used without further characterization. To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at – 0C was added -butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to -20 C over 20 minutes. After cooling to -78 C, 4-butyl-l -methyl- lH-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at -78 C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3 chi 20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give l -methyl-4-propyl-lH-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization

According to the analysis of related databases, 616-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; PROVID PHARMACEUTICALS INC.; EBRIGHT, Richard H.; EBRIGHT, Yon W.; SHEN, Juan; BACCI, James; HIEBEL, Anne-Cecile; SOLVIBILE, William; SELF, Christopher; OLSON, Gary; WO2013/192352; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

To a 50mL Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-iodobutane (13.8g, 0.075 mol, 1.5 equiv) and distilled toluene (20 mL), the mixture were heated and stirred at 80 C oil bath for 3 hours, after reaction, all the versitile were removed under vacuo, the residue colourless oil were washed with 2-methoxy-2-methylpropane (3×20 mL), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium iodide (NHC precursor G) as colorless oil orlight yellow oil (77%, 10g).

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Quan; Liu, Shu; Ma, Ming; Cui, He-Zhen; Hong, Xi; Huang, Shuang; Zhang, Jing-Fan; Hou, Xiu-Feng; Synthesis; vol. 50; 6; (2018); p. 1315 – 1322;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

616-47-7, name is 1-Methyl-1H-imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C4H6N2

1-Methyl-1H-imidazole (20 g, 244 mmol) was dissolved in anhydrous THF (200 mL) under a nitrogen atmosphere. The solution was stirred at -78 C and n-BuLi (167 mL, 268 mmol) was added dropwise slowly at -78 C. After 1 h, CBr4 (97 g, 292 mmol) solution in anhydrous THF (200 mL) was added. The solution was stirred for 2 h at -78 C and for 1 h at room temp. The reaction mixture was quenched with saturated aqueous ammonium chloride (300 mL), extracted with ethyl acetate (2 x 200 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude compound was purified by silica gel chromatography eluting with 60% ethyl acetate in pet. ether to afford the title compound. LCMS (method B): rt = 1.89, [M+H]+= 161.

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BARTON, Nicholas Paul; BERTRAND, Sophie Marie; DOWN, Kenneth; GRAY, Matthew; (168 pag.)WO2019/141694; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem