Month: May 2021

Electric Literature of 109012-23-9, 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. 109012-23-9 name is Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, 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.

To a solution of ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate (500 mg, 2.20 mmol) in methanol (7.5 mL)-THF (15 mL) was added 2M aqueous sodium hydroxide solution (3.8 mL, 7.53 mmol) at room temperature. The mixture was stirred for 3 hr at 40C, neutralized with 1M hydrochloric acid, extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (200 mg) as a brown solid (yield 46%). 1H NMR (300 MHz, DMSO-d6) delta 3.96 (3H, s), 8.58 (1H, s). * The peak of “COOH group” was not observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26530-93-8, name is 1-Methyl-1H-benzo[d]imidazol-6-amine, 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 26530-93-8, Formula: C8H9N3

Acetic anhydride (1.08 ml, 11.4 mmol) was added to a solution of 1-methyl-1H- benzo[d]imidazol-6-amine (800 mg, 5.44 mmol) in dioxane (20 mL) at 0 °C. The mixture was stirred at room temperature for 16 hours, concentrated in vacuo, and the residue was diluted with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to provide the title compound; mass ion (ES+) of 190.4 [M+H]+.

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-Methyl-1H-benzo[d]imidazol-6-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; MOHANTY, Subhendu Kumar; LATTHE, Prashant R.; KUDUK, Scott D.; HOYT, Scott B.; (107 pag.)WO2017/155816; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

58442-17-4, name is 1H-Benzimidazole-5-carbaldehyde, 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. SDS of cas: 58442-17-4

General procedure: 4.94g (56.7mmol) of MnO2 were added to a solution of 1.40g (9.45mmol) of 7 in 50mL of MeOH. After 48hat rt, the mixture was filtered over slica and by evaporation 1.24g (90%) of compound 8 was isolated.

The synthetic route of 58442-17-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alvarez, Raquel; Gajate, Consuelo; Puebla, Pilar; Mollinedo, Faustino; Medarde, Manuel; Pelaez, Rafael; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 167 – 183;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 65039-05-6, The chemical industry reduces the impact on the environment during synthesis 65039-05-6, name is 1-Butyl-3-methylimidazolium iodide, I believe this compound will play a more active role in future production and life.

General procedure: Catholyte (0.10molL-1 of ionic liquid 1a-h in 5.0mL of organic solvent) and anolyte (2.0mL same solvent/electrolyte) were separated through a porous glass frit filled with methylcellulose in DMF-Et4N-BF4. The electrolysis was carried out, under N2 atmosphere at 25C, at a constant current (J=15mA·cm-2). After the consumption of 31C, the current was switched off, the anodic compartment removed and the catholyte analyzed by cyclic voltammetry at different time intervals from the end of the electrolysis

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-Butyl-3-methylimidazolium iodide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Feroci, Marta; Chiarotto, Isabella; D’Anna, Francesca; Forte, Gianpiero; Noto, Renato; Inesi, Achille; Electrochimica Acta; vol. 153; (2015); p. 122 – 129;,
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. 84243-58-3, name is 6-(4-(1H-Imidazol-1-yl)phenyl)-4,5-dihydropyridazin-3(2H)-one, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

To this mixture is added toluene (25mL), and the mixture is stirred, and the precipitated crystals are collected by filtration to give crude ethyl 6-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate. Subsequently, to a suspension of ethyl 6-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (2.88 g, 9.63 mmol) in methanol (70 mL) is added a 5N aqueous sodium hydroxide solution (4 mL), and the mixture is stirred at 20-25C for 30 minutes. The reaction solution is concentrated under reduced pressure, and water (50 mL) is added to the residue, and thereto is added a 4N aqueous hydrochloric acid solution until the pH value of the mixture becomes pH 1. The resulting suspension is stirred for 30 minutes, and filtered. The product remained on the filter is dried under reduced pressure at 50C. The obtained solid is suspended in toluene (25 mL), and heated to 110C, and further gradually cooled to 20-25C. The insoluble product is collected by filtration, and dried under reduced pressure to give 5-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (1.29 g).

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 84243-58-3.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1719761; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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 89088-69-7, category: imidazoles-derivatives

A mixture of 4-benzenesulfonyl-2,6-dichloro-pyridine (0.40 g, 1.39 mmol), 1-methyl- lH-imidazole-4-amine hydrochloride (0.22 g, 1.67 mmol) and DIPEA (0.7 mL, 4.16 mmol) in anhydrous DMSO (4.6 mL) was flushed with nitrogen and heated at 120 C in a sealed microwave vial (plastic lid) for 2 h. The mixture was then partitioned between EtOAc (20 mL) and saturated aqueous ammonium chloride solution (10 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash silica chromatography (eluting with 1-8% MeOH in DCM) to give the title compound as a yellow solid (0.14g, 82% purity, 24% yield). MS: m/z = 349.0 (M+H)+.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 20033-99-2, 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. 20033-99-2, name is 2-(Hydroxymethyl)-5-methoxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34: Synthesis of 2-chloromethyl-5-methoxy-lH-benzoimidazole 222[0265] 2-Chloromethyl-5-methoxy-l H-benzoimidazole 222 was synthesized in 1 step from (5- Methoxy-lH-benzoimidazol-2-yl)-methanol 221 as shown in Scheme 58.Scheme 58Step 1 – Preparation of2-chloromethyl-5-methoxy-lH-benzoimidazole (222): [0266] (5-Methoxy-lH-benzoimidazol-2-yl)-methanol (221, 0.5 g, 3 mmol) was combined with 30 mL dichloromethane. Thionyl chloride (0.51 mL, 7 mmol) was added and the reaction was stirred at room temperature for 2 hours. The reaction was concentrated. Ethyl acetate was added and washed with sodium bicarbonate saturated solution and brine. The organic portion was dried over anhydrous sodium sulfate, filtered through Celite and evaporated to dryness. The resulting desired compound was used without further purification. MS (ESI) : [M+lT] + == 197.2.

The synthetic route of 2-(Hydroxymethyl)-5-methoxybenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); A2;,
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. 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C21H24N2

Step 1: Synthesis of di-mu-chloro-tetrakis {2-[1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl-kappaN3]phenyl-kappaC}diiridium(III) (abbreviation: [Ir(iPrpim)2Cl]2) Into a 200-mL three-neck flask were put 2.0 g (6.6 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-imidazole (abbreviation: HiPrpim), 1 g (3.2 mmol) of iridium(III) chloride hydrate, 65 mL of 2-ethoxyethanol, and 20 mL of water, and the mixture was heated and stirred at 100 C. under a nitrogen stream for 6.5 hours. After reaction for the predetermined time, the reaction solution was filtered and a precipitate was washed with methanol to give a yellow solid. The yield was 1.9 g (1.1 mmol) and 71%. The synthesis scheme of Step 1 is shown in (f-1).

The synthetic route of 914306-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; TSUNOI, Toshiaki; INOUE, Hideko; ISHISONE, Takahiro; WATABE, Takeyoshi; (129 pag.)US2017/213989; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 184098-19-9, name is 3-(2-Methyl-1H-imidazol-1-yl)aniline, 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 184098-19-9, Recommanded Product: 184098-19-9

5.4 l-[2-(2,6-Dioxo-piperidin-3-ylM-oxo-2,3-dihvdro-l//-isoindol-5- ylmethyll-3-[3-(2-methyl-imidazol-l-yl)-phenyll-urea; formic acid; A mixture of 3-(5-aminomethyl-l-oxo-l,3-dihydro-isoindol-2-yl)-piperidine-2,6- dione methanesulfonic acid salt (0.40 g, 1.1 mmol) and CDI (0.19 g, 1.2 mmol) in DMF (5 mL) was stirred at RT for 18 hrs. To the mixture was added 3-(2-methyl-imidazol-l-yl)-phenylamine (0.19 g, 1.1 mmol) at RT, and the mixture was stirred at 60 0C for 24 hrs. To the mixture was added water (25 mL) and ether (20 mL). The mixture was stirred at RT for 2 hrs. The suspension was filtered and the solid was washed with water (20 mL), ethyl acetate (20 mL), and water (20 mL) to give a solid. The solid was purified with preparative HPLC to give the product as a white solid (100 mg, 20% yield): HPLC: Waters Symmetry Ci8, 5 mum, 3.9 x 150 mm, 1 mL/min, 240 nm, 5% gradient 95% in 5 min, CH3CN/0.1% H3PO4, 4.48 min (96.8 %); mp: 218-220 0C; 1H NMR (OMSO-d6) delta 1.89 – 2.12 (m, IH, CHH), 2.25 – 2.29 (m, 3H, CH3), 2.30 – 2.46 (m, IH, CHH), 2.54 – 2.68 (m, IH, CHH), 2.78 – 3.04 (m, IH, CHH), 4.31 (d, J= 17.4 Hz, IH, CHH), 4.38 – 4.53 (m, 3H, CHH, CH2), 5.11 (dd, J= 5.1, 13.2 Hz, IH, NCH), 6.89 (d, J= 1.3 Hz, IH, Ar), 6.92 – 7.05 (m, 2H, Ar, NH), 7.23 (d, J= 1.3 Hz, IH, Ar), 7.32 – 7.40 (m, 2H, Ar), 7.41 – 7.49 (m, IH, Ar), 7.52 (s, IH, Ar), 7.57 – 7.65 (m, IH, Ar), 7.69 (d, J= 7.9 Hz, IH, Ar), 8.18 (s, IH, HCOOH), 9.03 (s, IH, NH), 10.98 (s, IH, NH); 13C NMR (DMSO-(Z6) ^ 13.60, 22.49, 31.20, 42.77, 47.12, 51.58, 114.22, 116.89, 117.61, 120.68, 121.88, 122.93, 126.89, 127.13, 129.63, 130.30, 137.90, 141.50, 142.38, 143.43, 144.69, 155.16, 163.44, 167.93, 170.98, 172.85; LCMS MH+ = 473; Anal. Calcd. for C25H24N6O4 + HCOOH + 1.5 H2O: C, 57.24; H, 5.36; N, 15.40; Found: C, 57.43; H, 5.11; N, 15.57.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(2-Methyl-1H-imidazol-1-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE CORPORATION; MULLER, George, W.; RUCHELMAN, Alexander, L.; WO2010/53732; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4919-03-3,Some common heterocyclic compound, 4919-03-3, name is 1H-Imidazol-4-amine, molecular formula is C3H5N3, 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 method for the synthesis of 4-nitroimidazole by oxidation with 4-aminoimidazole is described in detail below: Step S1, Oxidation: 83 g of 4-aminoimidazole were added to the flask, followed by 750 g of waterAnd 700 g of potassium peroxymonosulfate at 35 C for 16 hours; Step S2, extraction:The reaction solution was extracted with methylene chloride to give a methylene chloride layer; in Step S3,The dichloromethane layer was subjected to distillation under reduced pressure at a temperature of 30 C and a degree of vacuum of 0.07 MPa, and dichloromethaneMethane evaporated, the remaining material is 4-nitroimidazole. The content of 4-nitroimidazole was detected94.8%, and the yield was 92.4%.

The synthetic route of 4919-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui National Star Biochemical Co; Wei, Yongfei; Liang, Xichen; Fang, Hongxin; Huang, Chengqiang; Wu, Zongming; Wang, Xiaosheng; (6 pag.)CN106008353; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem