Author: Jessica.F

Electric Literature of 53710-78-4, 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under ice-cooling, 1-(3-chloropropyl)-1H-imidazole (1.90 g, 13.14 mmol), cesium carbonate (4.28 g, 13.14 mmol) and a catalytic amount of potassium iodide were dissolved in DMF (30 mL).2-Fluoro-4-nitroaniline (1.38 g, 8.84 mmol) was added in one portion and the reaction was heated to reflux for 36 h.After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solvent was evaporated under reduced pressure. The residue was added to water (50 mL) and extracted with dichloromethane (20 mL ¡Á 2).The organic phase was washed with saturated brine (20 mL¡Á2), the solvent was evaporated under reduced pressure, and the crude product was purified by column chromatography (dichloromethane/methanol (V/V)=15/1).A yellow oil (2.85 g, 82%) was obtained.

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-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 19225-92-4,Some common heterocyclic compound, 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole, molecular formula is C5H7ClN2, 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.

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40 C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate, the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (11 mg, 29%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6514971; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

17289-25-7, name is (1-Methyl-1H-imidazol-4-yl)methanol, 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. Quality Control of (1-Methyl-1H-imidazol-4-yl)methanol

190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 % yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).

The synthetic route of 17289-25-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); 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. 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, This compound has unique chemical properties. The synthetic route is as follows., name: (1H-Imidazol-1-yl)(phenyl)methanone

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

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 10364-94-0.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, A new synthetic method of this compound is introduced below., Quality Control of 2-(1H-Imidazol-1-yl)ethanol

Add sodium hydride (0.79 g; 1.1 equiv; 19.75 mmoles) slowly to a 0 C. solution of 1H-imidazole-1-ethanol (2.01 g; 1.0 equiv; 17.93 mmoles) in tetrahydrofuran (90 mL). Stir for 1 hour, then add acetic acid, bromo-, 1,1-dimethylethyl ester (4.03 mL; 1.49 equiv; 26.76 mmoles) dropwise at 0 C. Warm the solution to ambient temperature and stir for 3 hours, then add 250 mL saturated aqueous sodium bicarbonate solution. Extract the mixture with dichloromethane (3*150 mL). Wash the combined organic extracts with brine (100 mL), dry over sodium sulfate, filter, and concentrate to afford the crude product. Purify this residue by column chromatography (0 to 20% methanol in dichloromethane) to afford tert-butyl 2-(2-imidazol-1-ylethoxy)acetate (0.85 g; 21%) as a viscous yellow-brown oil: MS (m/z): 227(M+1).

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; Eli Lilly and Company; Beauchamp, Thomas James; Dao, Yen; Jones, Spencer Brian; Norman, Bryan Hurst; Pfeifer, Lance Allen; US2014/200231; (2014); 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, A new synthetic method of this compound is introduced below., Safety of 2-(1-Trityl-4-imidazolyl)benzaldehyde

5-Acetylbenzofuran-2-carboxylic acid methyl ester (0506-89) (200 mg, 0.86 mmol, 1.0 equiv) and2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (534 mg, 1.3 mmol, 1.5 eq.)Soluble in ethanol (10 ml),Concentrated sulfuric acid 5 ml was added dropwise under ice bath conditions.The temperature was raised to 90C and the reaction was stirred for 18 hours.Cool to room temperature, add dropwise to ice water, add ice bath, add sodium hydroxide to adjust the pH>8, ethyl acetate extraction,The liquid was separated, spin-dried, and the crude product was purified by silica gel column chromatography (eluent: dichloromethane/methanol=200/1 to 40/1) to give the product 5-(2-(5H-imidazole)[5,1-a Ethyl isomorpholin-5-yl)acetyl)benzofuran-2-carboxylate (95 mg, 28.5%).

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; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1403474-70-3, 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. 1403474-70-3, name is Ethyl 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of azilsartan ester (VI; Ri= Et) (25 g) and 0.4 N NaOH solution (380 ml) was heated at 70-75C for 90 minutes. The reaction mixture was cooled to 10-15C and the pH was adjusted to 2.5-3.0 with 2 N HC1. The mixture was stirred for 30 minutes at 10- 15C. The solid was filtered, washed with water (100 ml) and dried under vacuum. Yield: 22.0 g;X-ray powder diffraction pattern as depicted in figure 1.

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, Ethyl 2-ethoxy-1-((2′-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LUPIN LIMITED; ANSARI, Shahid, Akhtar; HIRPARA, Hitin, Maganbhai; BHATT, Nikhil, Shashikant; BARIA, Reenaben, Ratansing; YADAV, Ashok, Keshavlal; PATEL, Manishkumar, Baldevlal; WO2014/49512; (2014); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

Related Products of 50995-95-4, 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 50995-95-4 as follows.

[0675] A solution of 2-propylimidazole (76 mg, 0.69 mmol) in 1 mL DME was added to a mixture NaH (32 mg, 0.81 mol, 60% dispersion in mineral oil) at 0 C under argon. After 20 min, a solution of the product of Example 157 Step 3 (250 mg, 0.62 mol) in 2 mL DME was added at 0 C. The reaction was warmed to 25 C. After 1.5 h, the reaction was filtered through a pad of Celite (1″), and washed with EtOAc (20 mL). The filtrate was concentrated to give a pale brown oil in 0.21 g (80%).

According to the analysis of related databases, 50995-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, A common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

B. 1-(1-Trityl-1H-imidazol-4-yl)ethanol (cas No.62256-50-2) To 1-trityl-4-carboxaldehyde-1H-imidazole (11.7 g, 34.6 mmol) in THF (250 ml) at 0 C. is added methylmagnesium bromide (12.6 mL, 38 mmol, 3.0 M in diethyl ether). The reaction mixture is stirred at 15 C. for 4 h before quenching with water (10 mL), followed by aqueous ammonium chloride. The reaction is extracted into ethyl acetate and washed with 30 mL of saturated aqueous sodium bicarbonate. The organic solvent is removed in vacuo. Chromatography (silica gel, ethyl acetate:hexanes, 1:1 to 1:0) yields the desired product. MS (ESI) m/z 355 (M+H). (prepared similarly in J. Med. Chem. 1977, 20(5), 721)

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ksander, Gary Michael; Meredith, Erik; Monovich, Lauren G.; Papillon, Julien; Firooznia, Fariborz; Hu, Qi-Ying; US2007/49616; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem