Month: June 2021

Application of 39021-62-0,Some common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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 solution of l-methyl-lH-imidazole-5-carboxaldehyde (500 mg, 4.45 mmol) in tetrahydrofuran (5 ml), 4-fluorophenylmagnesium bromide (1.0 M solution in tetrahydrofuran, 6.20 ml, 6.20 mmol) was added dropwise at 0 C over 5 minutes andstirred at 0 C for 30 minutes. The reaction was quenched with saturated aqueousNH4CI solution (30 ml), extracted with chloroform (50 ml x 3), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (ethyl acetate/methanol, 100/0-90/10) to give (4- fluorophenyl)(l -methyl- lH-imidazol-5-yl)methanol (443 mg, 48 %, colorless solid).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; EURO-CELTIQUE S.A; WO2008/8398; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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 641571-11-1 as follows.

Method II; To a flask was added 6-methyl-5-[4-(pyrid-3-yl)pyrimid-2-ylamino) nicotinic acid (30.7 g) and SOCl2 (500 mL) and the reaction mixture was refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to give a solid, which is used for the next step directly. To the above acid chloride was added a clear solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (24.1 g) in pyridine (200 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and then the residue was added with chloroform (500 mL) and water (500 mL) and extracted. The organic phase was dried, filtrated, concentrated, and purified through column chromatography to give the titled compound.

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun, Piaoyang; EP1840122; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1615-14-1, A common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

Into a round bottom flask was added 057 (2.331 g, 0.003345 mol), triphenylphosphine (1.14 g, 0.00435 mol) and tetrahydrofuran (13.6 mL, 0.167 mol). The mixture was cooled to O0C under a nitrogen atmosphere. Imidazole ethanol fragment (0.450 g, 0.00401 mol) was added, followed by addition on diethyl azodicarboxylate (0.685 mL, 0.00435 mol). The reaction was allowed to warm slowly to room temperature while stirring. A TLC test revealed an intense product spot together with some unreacted starting material. The reaction was cooled to O0C and an additional 0.2eq of the amine, triphenylphosphine, and DEAD were added. The ice bath was removed and reaction was allowed to warm to room temperature. After 30min, TLC showed the reaction was complete and all starting material was consumed. All solvent was removed under high vacuum. The residue was dissolved in MTBE, the mixture was cooled in an ice bath and some of the triphenyl phosphate was filtered off. The residue was purified on 4Og column, using 0-5%MeOH/DCM. Product fractions containing compound 066 were combined and concentrated down to a residue. Yield: 3.65g(100%).

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; EISAI R & D MANAGEMENT CO., LTD.; WO2009/15368; (2009); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-38-6,Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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.

Preparation Example 22 1-(2-Cyanoethyl)-4-nitroimidazole: 4-Nitroimidazole (6.87 g, 60 mmol), triethylamine (18.2 g, 180 mmol) and acrylonitrile (9.55 g, 180 mmol) were dissolved in N,N-dimethylformamide (100 ml), and the solution was stirred at 100 C. for 5 hours. The reaction mixture was concentrated under reduced pressure, and chloroform was added to the concentrate. Solids deposited were collected by filtration and dried to obtain 9.2 g of the title compound. mp: 112-113 C.; 1 H-NMR (DMSO-d6) delta: 7.94(1H,d,J=1.2 Hz), 8.52(1H,d,J=1.2 Hz), 3.20(2H,t,J=7.2 Hz), 4.46(2H,t,J=7.2 Hz). Mass (FAB(+)) m/e: 167 (MH)+.

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taiho Pharmaceuticals Co., Ltd.; US6110967; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3752-24-7, name is 4,5,6,7-Tetrahydro-1H-benzo[d]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 3752-24-7, name: 4,5,6,7-Tetrahydro-1H-benzo[d]imidazole

A mixture of 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (5.00 g, 40.9 mmol), 90% KOH (3.74 g, 60 mmol) and DMSO (70 mL) was stirred under argon and heated at 40 C for 2 h. After cooling to 10 C, 1-bromohexane (6.3 mL, 45 mmol) was addedin one portion, and the resulting mixture was stirred and heated at 40 C for 4 days.The reaction mixture was poured into ice/water (600 mL), treated with 5 N NaOH(100 mL) and extracted with DCM (2 x 400 mL). The extract was washed with water(300 mL), dried over Na2SO4, and the solvent was removed under reduced pressureto give a residue. Column chromatography of the residue (silica gel, ethylacetate/methanol, 97:3) afforded pure 1-hexyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole (6.54 g, 77% yield).

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; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; WANG, Peng; (42 pag.)WO2018/191238; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 693-98-1, 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. 693-98-1, name is 2-Methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Synthesis of 2-methyl-1-aryl-1H-imidazole 5: To a stirring solution of 2-methyl- 1H-imidazole 4 (800 mg, 9.74 mmol) in 6 mL anhydrous dimethyl sulfoxide under argon was added iodobenzene (1.09 mL, 9.74 mmol), copper(I) iodide (185 mg, 0.97 mmol) and anhydrous potassium carbonate (2.69 g, 19.49 mmol). The reaction mixture was then heated to 130 C and allowed to stir for 48 hours in a sealed tube. Following completion of the reaction, the mixture was transferred to a separatory funnel containing ethyl acetate (200 mL) and the crude product was washed with water (4×40 mL) and brine (2×30 mL) before the organic layer was collected and dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The product was purified via flash column chromatography using hexanes :ethyl acetate (1:1 to 1:4) to elute pure 2-methyl-i -phenyl- 1H-imidazole 5 as a clear oil (730 mg, 47%). [00264] Yield: 47% yield; 730 mg of 5 was isolated as a clear oil. ?H NMR (400 MHz, CDC13): 7.51 -7.37 (m, 3H), 7.30 -7.22 (m, 2H), 6.98 (dd, J = 9.7, 1.4 Hz, 2H), 2.35 (s, 3H). ?3C NMR (100 MHz, CDC13): 144.8, 138.2, 129.6, 128.3, 127.8, 125.6, 120.8, 13.9.Note: NMR spectra match those previously reported.?

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

Reference:
Patent; UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INCORPORATED; HUIGENS, Robert, William; ABOUELHASSAN, Yasmeen; BASAK, Akash; (220 pag.)WO2018/106922; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 46006-36-4, 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 46006-36-4 as follows.

3H-Benzoimidazole-4-carboxylic acid[3-(1H-tetrazol-5-yl)-phenyl]-amide (16) 3-(1H-Tetrazol-5-yl)aniline (75 mg, 0.47 mmol), 1H-benzimidazole-4-carboxylic acid (76 mg, 0.47 mmol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (135 mg, 0.7 mmol), 1-hydroxybenzotriazole (95 mg, 0.7 mmol) and N,N’-diisopropylethylamine (0.17 mL, 0.94 mmol) was stirred in DMF (0.5 mL) at room temperature for 24 h. The reaction mixture is diluted with water (2 mL) and after approximately adjusting the pH to 4 with 1N HCl, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC to afford the product as a trifluoroacetic acid salt in 5% yield. 1H NMR (DMSO-d6) delta 8.62 (s, 1H), 8.53 (s, 1H), 7.99-8.02 (m, 3H), 7.86 (d, J=8 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 7.62 (t, J=8 Hz, 1H), 7.43 (t, J=8 Hz, 1H), 7.04 (s, 1H); LCMS (ESI) m/z 306 (MH+).

According to the analysis of related databases, 46006-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Chen, Yu; Nichols, Derek; Renslo, Adam R.; Jaishankar, Priyadarshini; Lauterwasser, Erica M. W.; (29 pag.)US9556131; (2017); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 150 mL round-bottomed flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is nitro) (0.361 g, 2.04 mmol) was added, and potassium carbonate was used as a base (0.324 g, 2.35 mmol) of acetonitrile as solvent. After stirring at 70C for 30 minutes, the mixture was cooled to room temperature and Compound II (0.400 g, 1.57 mmol) was added to continue the reaction and the temperature was raised to 70C. TLC followed the reaction to completion. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-3 (0.449 g) was obtained with a yield of 66.1%.

The synthetic route of 2-Methyl-5-nitro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Ge Pala·lawaya; Wang Yanan; Fang Xuejie; (27 pag.)CN107721933; (2018); A;,
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 78581-99-4 as follows. name: 5,6-Difluorobenzimidazole

Step 3: To a stirred mixture of sodium hydride (60% dispersion in mineral oil, 0.144 g, 3.0 mmol) in anhydrousDMF (10 mL) at 0 C under a nitrogen atmosphere was added portionwise 6-difluoro-1H-benzo[d]imidazole (0.475 g,2.0 mmol) from the previous step. The mixture was stirred at 0 C for 5 min. To the mixture was added dropwise asolution of 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (0.32 g, 2.0 mmol) from Step 4 of Example 36 in anhydrousDMF (2 mL). The reaction mixture was allowed to warm to rt and stir for 1 h. The mixture was poured into ice-water andextracted with EtOAc (100 mL 3 2). The combined organic layers were further washed with water (20 mL) then brine(20 mL). The organic layer was separated and dried over Na2SO4, filtered, and concentrated under reduced pressureto afford 6-((5,6-difluoro-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (0.55 g, 76%) as a yellow solid,which was not purified further. 1H NMR (300 MHz, CDCl3) delta 7.97 (s, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.59 (m, 1H), 7.50(s, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 5.40 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 348 (M + H)+.

According to the analysis of related databases, 78581-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 124312-73-8, A common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, molecular formula is C5H9N3, 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.

General procedure: To a solution of K2PtCl4 (0.208 g, 0.500 mmol) in 16 mL of H2O/HCl 4 M (ratio 15/1), the diamine (0.500 mmol) was added. The mixture was stirred for 6 h and heated under reflux, then it was warmed to room temperature and stirred overnight. The complex was filtered off and washed with water, methanol and diethyl ether. The solid was dried under vacuum at room temperature.

The synthetic route of 124312-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ferri, Nicola; Cazzaniga, Stefano; Mazzarella, Luca; Curigliano, Giuseppe; Lucchini, Giorgio; Zerla, Daniele; Gandolfi, Raffaella; Facchetti, Giorgio; Pellizzoni, Michela; Rimoldi, Isabella; Bioorganic and Medicinal Chemistry; vol. 21; 8; (2013); p. 2379 – 2386;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem