Month: December 2020

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. 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

a) A mixture of potassium carbonate (832 mg, 6.02 mmol), 2-methyl-5-(trifluoromethyl)-1H-imidazole (450 mg, 3.00 mmol) and ethyl 2-bromopropanoate (0.43 mL, 3.3 mmol) in dimethylformamide:tetrahydrofuran (2 mL:4 mL) was heated at 50 C. for 7 h with stirring and then at room temperature overnight. Most of the tetrahydrofuran was removed by gently blowing nitrogen over the reaction mixture. Ethyl acetate and water were then added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 17-50% ethyl acetate in hexanes) to afford the desired product (697 mg, 2.79 mmol, 93%).

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; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 930-62-1, 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 930-62-1 as follows.

1. Preparation of 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one. A solution of 2,4-dichlorobenzoyl chloride (7.24 M) in dichloromethane (25 ml) was added dropwise over 20 minutes to a stirred solution of 2,4-dimethylimidazole (0.80 M) in dichloromethane (75 ml) and N,N-diisopropylethylamine (Huenig’s base) (34 ml). The reaction mixture was cooled during the addition using a water bath. The reaction mixture was then heated to reflux for 5 hours. The reaction can turn a darker color. The product was stripped of solvent under reduced pressure, and the resulting solid was dried in vacuo for one hour. To the dry solid (described above) was added a solution (2:1 v/v, 120 ml) of gla. acetic acid and aq. con. HCl. The mixture was then stirred at reflux for ca. 90 min. The acetic acid was removed via rotary evaporator. Upon cooling, distilled water (200 ml) and toluene (100 ml) were added to the solid residue, which was vigorously stirred for 30 min. The solids were filtered, rinsed with 50 ml distilled water, and discarded. The filtrate was transferred to a separatory funnel. After the organic layer was discarded, the aqueous layer was washed with toluene (2¡Á100 ml). The aqueous layer was transferred to a large beaker (2 L) and diluted with isopropyl ether (50 ml). The stirred mixture was basified (pH 7-8) by careful addition of sodium bicarbonate which leads to the formation of a sticky white solid. Dichloromethane (200 ml) was added and stirring continued for 10 min. The organic layer was separated and the aqueous layer was again extracted with dichloromethane (100 ml). The organic layers were combined and washed with sat. aq. NaHCO3 (100 ml), distilled water (100 ml), brine (100 ml), dried with Na2SO4, filtered, concentrated, and dried in vacuo giving 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one in 46% yield.

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bennett, Christina N.; Hankenson, Kurt D.; Harrison, Stephen D.; Longo, Kenneth A.; MacDougald, Ormond A.; Wagman, Allan S.; US2005/54663; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6154-30-9, 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. 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-nitroimidazole (25 g, 221 mmol), sodium bicarbonate (37.1 g, 442 mmol) and water (600 mL) for dilution and then bromine (30 mL, 620 mmol) the temperature at the dropwise addition and the reaction mixture was at 40 C and reacted for 12 hours. After filtering the solids level of the reaction mixture was washed with toluene three times and dried under reduced pressure to give a yield of 2,5-dibromo-4-nitroimidazole of 39.8 g (67%). Prepared 2,5-di-bromo-4-nitroimidazole (39.8 g, 149 mmol) and water (450 mL) and then diluted to sodium iodide (223 g, 1486 mmol) was added and stirring under reflux was 12 sigan. Lower the temperature to room temperature, then filtered washing the solids in the reaction mixture with water, dried under reduced pressure to yield 2-bromo-5-iodo of 37.6 g (80%) was obtained a 4-nitroimidazole. Prepared 2-bromo-5-iodo-4- nitroimidazole (20 g, 63 mmol) in ethanol (190 mL) and then diluted in triethylamine (26.5 mL, 190 mmol) and platinum oxide (108 mg, 0.47 mmol) to give the applied wave after reacting for 3 hours under a hydrogen pressure of 3 bar in the reactor was concentrated under a reduced pressure after filtration with a silica gel and celite. Yield of the reaction mixture with 2-ethyl acetate 10% washed with hydrochloric acid solution to remove the moisture of the obtained organic layer over anhydrous magnesium sulfate, and then the filtrate was concentrated under reduced pressure and isopropyl alcohol and hexane, to obtain 7.9 g (65%) and then diluted with to give a-bromo-4-nitroimidazole.

The synthetic route of 2,5-Dibromo-4-nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Kim, Phill Ho; Lee, Sang Ho; Kim, Soo Hyun; Lee, Ir Young; Yoon, Chang Soo; Oh, Tae Kwon; Cho, Sang Rae; (18 pag.)KR101650716; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 53981-69-4, 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. 53981-69-4 name is 1-(1H-Imidazol-2-yl)ethanone, 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 an ice coled solution of 1-(1H-imidazol-2-yl)ethanone (2.0 g) in MeOH (36 mL) was added NaBH4 (0.69 g). After stirring for 30 minutes at 0C, the reaction mixture was concentrated in vacuo. The residue was purified with amino-type silica gel column chromatography (0- 10 % MeOH in CHCb) to give the title compound (lntermediate-3, 1.9g, 96 % yield) as colorless solid. -NMR data of Intermediate -3 is shown in Table 1.

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; SASAKI, Toru; TANAKA, Nozomi; OTAKE, Norikazu; TSURUTA, Risa; YAMADA, Yousuke; MATSUDA, Yohei; OGATA, Yuya; (346 pag.)WO2018/216822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2625-49-2, name is 2-(1-Methyl-1H-imidazol-4-yl)acetic acid, 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 2625-49-2, COA of Formula: C6H8N2O2

EXAMPLE 53A {4-[4-(1-Methylimidazol-4-yl)-3-keto-1-butynyl]-2-phenylbenzoyl}-methionine methyl ester To a solution of 1-methyl-4-imidazoleacetic acid (5 mmol) in methylene chloride at 0 C. is added oxalyl chloride (6 mmol) and DMF (0.05 mmol). After 30 minute, the solvent is evaporated in vacuo. The residue is redissolved in dichloromethane, followed by the addition of the resultant acetylene from Example 47A (5 mmol), triethylamine (10 mmol), and copper(I) iodide (1 mmol). The reaction is stirred at 25 C. until TLC analysis indicates no starting material is left in the reaction mixture. The reaction is diluted with ether, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified by column chromatography on silica gel to give the title compound.

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; University of Pittsburgh; US6310095; (2001); B1;; ; Patent; University of Pittsburgh; US2002/193596; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7757-21-3, 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. 7757-21-3 name is (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, 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.

2,4-Dichloro-benzylamine (47.3mg 0.269mmol) and 3,4-diraethoxy-3- cyiclobutene-l,2-dione (38.2mg, 0.269mmol) were combined in MeOH (2 ml) and water 104 (2ml) and stirred for 2h. C-(lH-benzoimidazol-2-yl)-methylamine HCI (59.4 mg, 0.269mmol) and sat. aHC( (lml) was added in situ. The mixture was stirred at room temperature overnight. After the mixture was extracted with ethyl acetate, washed with brine, concentrated under vacuum and purified via flash column chromatography to yield 3- [(lH-Benzoiniidazol-2-ylmemyl)-amino]-4-(2,4-dicUoro-benzylam dione(1769). LC/MS: (ESI) (M l i s 402.5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (1H-Benzo[d]imidazol-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

Intermediate 80: step a (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifiuoromethyl)benzyl)quinoiine (Intermediate 12: step d, 3.0 g, 6,97 mmol) was added THF (40 ml) and the solution was cooled to -70 C. K-BuLi (2.5 M in hexanes, 2.8 mL, 7 mmol) was added dropwise. After 2 minutes, 1- methyl-lH-imidazole-5-carbaldehyde (1.2 g, 9 mmol, in 10 mL THF) was introduced. After 15 minutes, the dry-ice bath was replaced with a 0 C bath. After 35 minutes the reaction mixture was quenched with aqueous NH4CI solution and the aqueous portion was extracted with EtOAc:THF (10:2) 5 x 50 mL. The combined organics were washed with brine, dried over Na2S04, filtered and concentrated to dryness to give the title compound.

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; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 172499-76-2, 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. 172499-76-2 name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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.

General procedure: A suspension of tBuOK (1.1 equiv. or 2.2 equiv.) and the imidazole derivative (1.0 equiv.) in DMF (6 mL/mmol) was stirred at rt for 1 h. The reaction mixture was treated with the corresponding alkyl bromide or alkyl mesylate (1.3 equiv. or 2.0 equiv.) and the temperature was raised up to 60 C and stirred at this temperature for 72 h. The solution was then diluted with EtOAc (20 mL/mmol) and washed three times with brine and H2O. The organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by CC.

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

Reference:
Article; Kerscher-Hack, Silke; Renukappa-Gutke, Thejavathi; Hoefner, Georg; Wanner, Klaus T.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 852 – 880;,
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. 51-17-2, name is 1H-Benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6N2

To a stirred solution of 1H-benzo[d]imidazole (2 g, 16.94 mmol) in acetic acid (25 mL) under an inert atmosphere was added 10% Pd/C (50% wet, 600 mg) at room temperature. The reaction mixture was stirred at 90-95 C. under a hydrogen atmosphere (75 PSI) for 24 h. After consumption of starting material (by TLC), the reaction mixture was filtered through a pad of celite and the pad was washed with EtOAc (100 mL). The filtrate was basified with saturated sodium bicarbonate solution (100 mL) and extracted with EtOAc (2*100 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain 4,5,6,7-tetrahydro-1H-benzo[d]imidazole (800 mg, 6.55 mmol, 40%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.52 (brs, 1H), 7.35 (s, 1H), 2.45 (brs, 4H), 1.74-1.67 (m, 4H)

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 51-17-2.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; (93 pag.)US2018/186773; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of mutilin (93g, 0.29 mole) in EtOAc (1 L) was cooled to -45 0C (CH3CN/dry ice bath) with mechanical stirring under nitrogen. Trifluoroacetyl imidazole (Aldrich, 5 x 1Og ampules, 5Og, 0.30 mole) was then added dropwise over 30-45 minutes. After stirring for 1 hour, TLC (10% EtOAc/hexanes) showed complete consumption of mutilin. The mixture was allowed to ward to – 200C, and was then washed with IN HCl (2 x 30OmL), water, brine and then was dried over magnesium sulfate and filtered. After concentration to 300-40OmL, IL of hexanes was added with stirring. The precipitated product was filtered and washed with hexanes (IL) to afford pure 11-OTFA-mutilin as a white crytalline solid (55g). Additional product was obtained by evaporating the filtrate, and stirring the residue in ethyl ether (10OmL), and diluting with hexanes (40OmL). Filtration and washing with hexanes gave a second crop (47g) which was ~90% pure by NMR.

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem