Month: June 2021

Reference of 33543-78-1, The chemical industry reduces the impact on the environment during synthesis 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, I believe this compound will play a more active role in future production and life.

Example 3A Ethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazole-2-carboxylate 0.5 g (3.6 mmol) of imidazole-2-carboxylate ethyl were dissolved in 35 ml of acetone, and 0.96 g (3.6 mmol) of 2-bromo-2,4-dichloroacetophenone and 0.49 g (3.6 mmol) of potassium carbonate were added. The mixture was stirred at RT for 12 h. The reaction mixture was concentrated and taken up in water and dichloromethane. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was triturated with diethyl ether and the solid was filtered off with suction. This gave 0.9 g (77percent of theory) of the product as a solid. LCMS (method 1): Rt=1.19 min. (m/z=327 (M+H)+) 1H-NMR (400 MHz, DMSO-d6): delta=7.96 (d, 1H), 7.84 (d, 1H), 7.68 (dd, 1H), 7.5 (s, 1H), 7.16 (s, 1H), 5.87 (s, 2H), 4.22 (q, 2H), 3.32 (s, 2H), 1.23 (t, 3H).

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 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/53929; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 616-47-7, These common heterocyclic compound, 616-47-7, name is 1-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.

To a 50mL Schleck tube was added 1-methyl-1H-imidazole (4.1g, 0.05 mol), 1-iodobutane (13.8g, 0.075 mol, 1.5 equiv) and distilled toluene (20 mL), the mixture were heated and stirred at 80 C oil bath for 3 hours, after reaction, all the versitile were removed under vacuo, the residue colourless oil were washed with 2-methoxy-2-methylpropane (3×20 mL), dried under vacuo, which afforded 3-butyl-1-methyl-1H-imidazol-3-ium iodide (NHC precursor G) as colorless oil orlight yellow oil (77%, 10g).

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Quan; Liu, Shu; Ma, Ming; Cui, He-Zhen; Hong, Xi; Huang, Shuang; Zhang, Jing-Fan; Hou, Xiu-Feng; Synthesis; vol. 50; 6; (2018); p. 1315 – 1322;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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 the corresponding benzimidazole or pyrazole 16?20 (4.5 or 6.6 equiv), dissolved under N2 atmosphere in anhyd MeCN, NaH (60percent dispersion in mineral oil, 4.5 or 6.6 equiv) was added and the mixture was stirred for 30 min at r.t. Then, the bromomethyl-substituted benzene derivative 15, 21 or 23 (1 equiv) was added and the reaction mixture was stirred for up to 5 d at r.t. under N2 atmosphere. The reaction was quenched with H2O (10 mL) and extracted with CHCl3 (3 × 10 mL). The organic layers were combined, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CHCl3?MeOH or CHCl3?MeOH?hexane as the eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromobenzimidazole, its application will become more common.

Reference:
Article; Koch, Niklas; Mazik, Monika; Synthesis; vol. 45; 24; (2013); p. 3341 – 3348;,
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. 1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Ethyl-1H-benzo[d]imidazole

A mixture of (5-chloro-7-morpholin-4-ylthiazolo[5,4-J]pyrimidin-2-yl)-[4-(l- hydroxy-l-methylethyl)piperidin-l-yl]methanone (250 mg, 0.59 mmol), 2- ethylbenzimidazole (90 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium (15 mg, 2.5 molpercent), XPhos (25 mg, 10 molpercent) and Cs2CO3 (270 mg, 0.83 mmol) in DMF (6 mL) was purged with argon then heated at 150 0C for 30 min in a microwave reactor. The reaction mixture was purified by column chromatography (Si-PCC, MeOH:DCM, 1-5percent) followed by recrystallisation from Et2O and EtOAc affording 771 (109 mg, 35percent). LCMS (method I): Rx 3.96 min [M+H]+ 536.3. 1H NMR (CDCl3, 400 MHz): delta 8.06-8.05 (1 H, m), 7.76-7.75 (1 H, m), 7.32-7.28 (2 H, m), 5.22 (1 H, d, J = 13.34 Hz), 4.84 (1 H, d, J = 13.16 Hz), 4.41 (4 H, brd s), 3.89 (4 H, t, J = 4.74 Hz), 3.37 (2 H, q, J = 7.46 Hz), 3.17-3.15 (1 H, m), 2.84-2.82 (1 H, m), 1.94 (2 H, t, J = 13.72 Hz), 1.72-1.62 (1 H, m), 1.49-1.40 (5 H, m), 1.23 (6 H, d, J = 7.01 Hz)

The synthetic route of 1848-84-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-47-3, The chemical industry reduces the impact on the environment during synthesis 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

COMPOUND 12.1. 11: NqN-DIETHYL-4- {7-METHOXY-2-[(2-PHENYL-1H- IMIDAZOL-5-YL) METHYL1-L24-TETRAHYDROISOOUINOLIN-1- YUBENZAMIDE; INTERMEDIATE 4.2. 2 (24 mg, 0.07 mmol) and 2-phenylimidazole-4 (5)- carbaldehyde (48 mg, 0.28 mmol) were dissolved in DCE (2.0 mL) and NMP (0.2 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (59 mg, 0.28 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman IPS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (13 mg, 0.026 mmol, 37%). lH NMR (500 MHz, CDC13) : 8 1. 10, 1.24 (2 brs, 6H), 2.73, 2. 82, 3. 00, 3.17 (4 m, 4H), 3.25, 3.54 (2 brs, 4H), 3.62 (s, 3H), 3.68 (m, 2H), 4.89 (s, 1H), 6.21 (s, 1H), 6.73 (d, J 8. 5 Hz, 1H), 6.90 (s, 1H), 7.05 (d, J 8. 5 Hz, 1H), 7.27-7. 38 (m, 7H), 7.90 (m, 2H). 13C NMR (125 MHz, CDC13): 6 12.8, 14.2, 26.4, 39.5, 43.4, 46.6, 49.1, 55.2, 66.9, 113.2, 113.8, 125.9, 126.5, 129.0, 129.7, 129.9, 157.9, 171.1. (+) LRESIMS m/z 495 [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, 2-Phenyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6160-65-2, The chemical industry reduces the impact on the environment during synthesis 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, I believe this compound will play a more active role in future production and life.

A solution of the amine (2.1 g, 8.7 mmol) in anhydrous CH2Cl2 (40 mL) was added dropwise over 2-5 minutes to an ice-NaCl bath cooled solution of 1,1?-thiocarbonyldiimidazole (95%, 3.1 g, 17.4 mmol, 2 eq.) in anhydrous CH2Cl2 (120 mL). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours after which time analysis by TLC (5% MeOH in CH2Cl2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (13 mL, 91 mmol, 10.5 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (5 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf SiO2 (120 g), 100% CH2Cl2?10% MeOH in CH2Cl2) gave the thiourea as an amber oil that solidified to a tacky residue upon standing (2.5 g, 96%).

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, 1,1′-Thiocarbonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Duke University; Liedtke, Wolfgang; (96 pag.)US2016/199363; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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.

Under N2 at -78 100 mL 3-neck round bottom flask at nBuLi (hexane of 2.5 M, 0.52 mL, 1.3 mmol) to dry THF (10 mL) of 6-bromo-2,4-dichloro-3 – phenyl quinoline (353 mg, 1 mmol, intermediate 1: step c) was added dropwise to a solution of. Continuous stirring for 30 minutes, was added a solution of dry THF (10 mL) of 1-methyl -1H- imidazole-5-carbaldehyde (110 mg, 1 mmol) at -78 . The cooling bath was removed and was gradually The mixture was warmed to RT, stirred for 2 hours. The mixture was then quenched by the addition of H2O (10 mL), extracted with CH2Cl2 (2 × 50 mL). Dry the combined organic phases with Na2SO4 and concentrated to dryness, prep-TLC: Purification of (CH3OH / CH2Cl2 1 evolves to 5) to give the title compound as a white solid.

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H8N2

Copper oxide (0.045 g, 0.316 mmol), 4,7-bis(methyloxy)-1 ,10-phenanthroline (0.228 g, 0.948 mmol), polyethylene glycol (1.248 g, 11.76 mmol), cesium carbonate (2.88 g, 8.84 mmol), 2,4-dimethyl-1 H-imidazole (0.729 g, 7.58 mmol) and 1 ,1-dimethylethyl3-chloro-5-iodobenzoate (D53, 2.139 g, 6.32 mmol) were transferred into a dried round-bottomed flask vial and capped with a rubber septum. The flask was then evacuated and backfilled with argon – this process was repeated several times. Butyronitrile (3.12 ml.) was then added and the mixture was stirred at 80 0C overnight during which time the reaction had evaporated to dryness. Further butyronitrile (3.12 ml.) was added and the mixture stirred at 80 0C over the weekend.The mixture was diluted with dichloromethane and then filtered through celite. The filtrate was concentrated in vacuo and the resulting crude material (2.8 g) was purified by flash chromatography with a gradient of 0 – 100% ethyl acetate in hexane to afford the title compound as a white solid.LC/MS (ES+ve): [M+H]+ at m/z 307, 309 (C16H19CIN2O2 requires [M+H]+ at m/z 307, 309)

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; GLAXO GROUP LIMITED; WO2009/819; (2008); 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: A mixture of tosylhydrazone 1 (1 mmol), thiol 2 (1.5 mmol, 1.5 equiv), K2CO3 (2.5 mmol, 2.5 equiv) in toluene (4.0 mL) was stirred at 100 C for 24h under Argon. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. After adding CH2Cl2 (10 mL), the organic phase was washed with saturated NaHCO3, brine and dried with Na2SO4, and concentrated under reduced vacuum. The residue was then purified by flash chromatography on silica gel to afford product 3.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2034-22-2, 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. 2034-22-2 name is 2,4,5-Tribromoimidazole, 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.

A dried 500 mL round bottom flask was charged with 2,4,5-tribromoimidazole (5 1, 20.0 g, 65.6 mmol) and anhydrous DMF (100 mL), and the resulting solution was cooled to 0C. To this cold solution was added NaH (60% in mineral oil, 2.80 g, 70.0 mmol) portionwise with gas evolution under control and an internal temperature maintained below l0C. After addition, the cold bath was removed and the resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was cooled back to 0C, and SEMC1 (12.2 mL, 69.5 mmol) was added to the reaction via syringe pump over 30 minutes. The reaction was stirred at 0C for an additional 30 minutes and at room temperature for another 30 minutes. The mixture was partitioned between EtOAc (150 mL) and water (300 mL), the organic phase was washed with dilute aqueous NaCl (5percent w/w) twice, then brine (100 mL), dried (Na2S04), and concentrated. The crude material was re-crystallized from hot petroleum ether (30 mL) and the solids were harvested from the mother liquor at 0C. The product was washed with cold petroleum ether (30 mL) and dried under vacuum to afford 2,4,5-tribromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (5_2). 1H MR (400 MHz, CDCh) d 5.31 (s, 2H), 3.59 (t, J= 7.2 Hz, 2H), 0.92 (t, J= 7.2 Hz, 2H), -0.01 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Tribromoimidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; CLAUSEN, Dane James; YU, Wensheng; KELLY, Joseph, M.; KIM, Hyunjin, M.; KOZLOWSKI, Joseph, A.; (202 pag.)WO2020/28150; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem