Author: Jessica.F

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., 288-32-4

c: 1-Benzyl-2-chloromethyl-imidazole, oxalate A solution of imidazole (13.6 g, 200 mmol) in 33% aqueous sodium hydroxide is heated to 100 C. for 10 min, the water is removed in vacuo and the crystalline sodium salt is dried at 0.1 mBar and 160 C. for 40 min. The salt is dissolved in 100 ml acetonitrile and is added benzylbromide 23.8 ml, 200 mmol). After stirring at 50 C. for 30 min, the mixture is concentrated in vacuo and the formed NaBr is removed by trituration in ethylacetate and filtration. On concentration in vacuo 1-benzyl-imidazole is obtained as an orange oil.

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; NeuroSearch A/S; US5296493; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, 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. 71759-89-2, name is 5-Iodo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a round-bottom flask was added 4-iodo-1H- imidazole (0.884 g, 4.557 mmol) and cesium carbonate (3.113 g, 9.554 mmol). The flask was capped, dimethylformamide (20 mL) was added, and the atmosphere was vacuum purged thrice with nitrogen. (1-bromoethyl)benzene (884 mg, 4.777 mmol) was added, and the reaction was heated at 80 C for 2 h. The reaction mixture was poured into water and extracted with twicewith ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluting with hexanes and ethyl acetate) to provide 4-iodo-1-(1-phenylethyl)- 111-imidazole (0.954 g, 3.2 mmol, 67%), as a clear yellow oil. LCMS M/Z (M+H) 298.8.

The synthetic route of 5-Iodo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 50995-95-4 name is 2-Propylimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 50995-95-4

EXAMPLE 12 1-(6-Methylergolin-8beta-ylmethyl)-2-propylimidazole 0.68 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.1 g of 2-propylimidazole and 50 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8beta-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2.5 hours. The solvent was distilled off under reduced pressure, and the residue was purified by alumina column chromatography (eluted with ethyl acetate_benzene=1:2, and then with ethyl acetate). The resulting product was recrystallized from acetone-hexane to obtain 0.8 g of the titled compound as colorless needles having a melting point of 223-227 C. (with decomposition). NMR (CDCl3) delta: 1.01 (3H, t, J=6.9 Hz), 1.17 (1H, q, J=12.0 Hz), 1.60-3.12 (11H, m), 2.43 (3H, s), 3.37 (1H, dd, J=14.4, 3.8 Hz), 3.78 (2H, d, J=6.8 Hz), 6.71-7.25 (6H, m), 7.94 (1H, br).

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

Reference:
Patent; Maruko Seiyaku Co., Ltd.; US4713457; (1987); A;,
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. 139481-72-4, name is Trityl candesartan belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 139481-72-4

Potassium carbonate (60 gm), 1-chloroethylcyclohexyl carbonate (60 gm) and potassium iodide (20 gm) were added to the solution of 2-Ethoxy-1-[[2′-(N- triphenylmethyltetrazole-5-yl)biphenyl)-4-yl]methyl]benzimidazole-7-carboxylic acid (100 gm) in dimethylformamide (500 ml) at room temperature. Raised the temperature to 750C, stirred for 2 hours, cooled to room temperature and 5% sodium chloride solution (2000 ml) was added. Maintained for 15 minutes, ethyl acetate (400 ml) was added, stirred and separated the layers. Aqueous layer was extracted with ethyl acetate (400 ml), organic layer was taken, washed with 10% sodium chloride solution (400 ml), concentrated, and co-distilled with ethyl acetate (100 ml). Mixture of ethyl acetate (500 ml) and n-hexane (500 ml) were added to the residual mass, stirred for 6 hours at room temperature, cooled to 50C, stirred for 1 hour, filtered, then washed with mixture of ethyl acetate (50 ml) and n-hexane (200 ml) and dried for 6 hours to obtain 1-(Cyclohexyloxy carbonyloxy)ethyl-2-ethoxy-1-[[2′-(1H-tetrazole-5-yl)biphenyl-4-yl]methyl] benzimidazole-7-carboxylate (110 gm, HPLC Purity: 99%).

The synthetic route of 139481-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO RESEARCH FOUNDATION; WO2009/157001; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, Adding some certain compound to certain chemical reactions, such as: 288-32-4, name is 1H-Imidazole, 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 288-32-4.

33.1 1-(4-nitrophenyl)-1H-imidazole: 9 g (64.5 mmoles) of potassium carbonate and 5 g (3.75 ml; 35.2 mmol) of 1-fluoro-4-nitrobenzene are added to a solution of 2 g of imidazole (29.4 mmol) in 14 ml of DMF. The reaction mixture is agitated for 1.5 hours at 110 C. Ethyl acetate (50 ml) is added to the medium which is washed 3 times with 50 ml of water. The organic phases are dried over magnesium sulphate and concentrated under vacuum. 4.4 g of product are thus obtained (yield=80%) in the form of a clear oil and used without further purification in the following stages. NMR 1H (CDCl3, 100 MHz, delta): 6.92 (t, 1H, Arom. H imidazole), 7.16 (s, 1H, Arom. H imidazole), 7.24-7.32-8.18-8.27 (4s, 4H, Arom. H), 7.59 (s, 1H, Arom. H imidazole).

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 288-32-4.

Reference:
Patent; Chabrier de Lassauniere, Pierre Etienne; Auvin, Serge; Bigg, Dennis; Auguet, Michel; Harnett, Jeremiah; US2003/78420; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, A common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, molecular formula is C8H7ClN2O, 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 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole 2-Chloro-5-methoxy-1H-benzimidazole (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Glaxo Wellcome Inc.; US6413938; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below.

To a suspension of 10 (4.94 g, 51.4 mmol) in dry THF (30 mL) was added NaH (2.48 g, assey 60%, 61.9mmol, 1.2 eq) at -78 C under argon atmosphere, and stirred for 10 min at rt. The reaction mixture was cooledto -78 C and added MeI (3.9 ml, 62.6 mmol, 1.2 eq) dropwise at -78 C. The mixture was gradually warmed to rt and stirred for 18 h. The mixture was quenched with MeOH, then concentrated in vacuo. The residue was dissolved with CH2Cl2 and the solution was filtered through a pad of Celite to afford the crude product, which was purified by silica gel chromatography (20:1 CHCl3 / MeOH) to afford 15 (5.58 g, 99%) as a yellow oil. 1H NMR (500 MHz, CDCl3) delta 3.79 (s, 3H), 7.53 (s, 1H), 7.60 (s, 1H), 9.88 (s, 1H)

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:
Article; Yamashita, Megumi; Shimizu, Keita; Koizumi, Yasuaki; Wakimoto, Toshiyuki; Hamashima, Yoshitaka; Asakawa, Tomohiro; Inai, Makoto; Kan, Toshiyuki; Synlett; vol. 27; 19; (2016); p. 2734 – 2736;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Adding some certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1.

Diethyl azodicarboxylate (174 mg, 1 mmol) was added to a solution of 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (288 mg, 0.5 mmol), triphenylphosphine (262 mg, 1 mmol) and 2-(imidazol-1-yl)ethanol (62 mg, 0.55 mmol), (J. Med. Chem. 1993, 25, 4052-4060), in methylene chloride (5 ml) and the mixture stirred for 1 hour at ambient temperature. Acetic acid (30 mg, 0.5 mmol) was added and the volatiles were removed by evaporation. The residue was triturated with ether, the solid collected by filtration and dried under vacuum to give 4-(4-chloro-5-diphenyl-t-butylsilyloxy-2-fluoroanilino)-7-(2-(imidazol-1-yl)ethoxy)-6-methoxyquinazoline (186 mg, 55%). MS – ESI: 668 [MH]+

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 1615-14-1.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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.

e) {(S)-3-[4-(5-Amino-6-methoxy-pyridin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-pyrrolidin-1-yl}-(1-methyl-1H-imidazol-4-yl)-methanone A solution of 1-methyl-1H-imidazole-4-carboxylic acid (CAS registry 41716-18-1) (36.0 mg, 0.26 mmol) and Et3N (0.11 ml, 0.78 mmol) in DMF (1 ml) was treated with HBTU (CAS registry 94790-37) (107 mg, 0.28 mmol). After stirring at rt for 20 min, the reaction mixture was cooled down to 5¡ã C. and a solution of 2-methoxy-5-[6-((S)-pyrrolidin-3-yloxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-pyridin-3-ylamine (88 mg, 0.26 mmol) in DMF (3 ml) was added. The reaction mixture was stirred at rt for 1 h, concentrated and the residue was taken up in DCM (10 ml), washed with a sat. aq. NaHCO3 soln. (5 ml), the organic layer was separated by elution through a separating phase cartridge and concentrated. The residue was purified by flash chromatography on silica gel (heptane/EtOAc 100:0 to 0:100), the combined fractions were concentrated, dissolved in tBuOH/H2O and lyophilized to afford the title compound as a colourless solid (21 mg, 37percent yield). UPLC RtM2=0.85 min; ESIMS: 451 [(M+H)+]. 1H NMR (400 MHz, CD3OD): delta 7.64 (s, 1H), 7.62 (s, 1H), 7.65 m, 1H), 6.93 (m, 1H), 6.70 (m, 1H), 6.20-6.34 (m, 1H), 6.15 (m, 1H), 4.81 (m, 1H), 4.19-4.31 (m, 2H), 3.90-4.05 (m, 4H), 3.55-3.83 (m, 8H), 2.04-2.28 (m, 2H).

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole, A new synthetic method of this compound is introduced below.

General procedure: The corresponding imidazole (2 mmol) and 2-bromoethanol or 3-bromo-1-propanol or 4-bromo-1-butanol (2.4 mmol) dissolved in acetone (20 ml). Then K2CO3(6 mmol) and KI (2 mmol) were added. The reaction mixture was stirred at 60oCfor 12h. Filtered, the filtrate was concentrated under reduced pressure and dried under vacuum. The1H-NMR and13C-NMR were consistent with the literature.

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:
Article; Hu, Yanping; Li, Na; Zhang, Jiayao; Wang, Ying; Chen, Li; Sun, Jianbo; Bioorganic and Medicinal Chemistry Letters; vol. 29; 9; (2019); p. 1138 – 1142;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem