Imidazoles-derivatives

23785-21-9, The chemical industry reduces the impact on the environment during synthesis 23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a stirred solution of XLIV, (2 g; 14 mmol) in dimethylformide (50 ml) was added trityl chloride (3.98 g; 14 mmol) and triethylamine (1.73 g, 17 mmol) at 0C. The resulting solution was stirred for 12 h at room temperature. The reaction mixture was cooled, concentrated at reduced pressure and diluted with water. The aqueous layer was extracted with ethyl acetate.The combined organic layers were washed with brine, dried over Na2504, filtered and concentrated under vacuum to afford ethyl 1 -trityl- 1 H-imidazole-4-carboxylate as a brown solid (XLV; 3 g, 55% yield). MS (M+1) 383.34.

The chemical industry reduces the impact on the environment during synthesis Ethyl 1H-imidazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NORGINE B.V.; BAKTHAVATCHALAM, Rajagopal; BASU, Manas Kumar; BEHERA, Ajit Kumar; VENKATESHAPPA, Chandregowda; HEWSON, Christopher Alexander; KADNUR, Sanjay Venkatachalapathi; KALINDJIAN, Sarkis Barret; KULKARNI, Bheemashankar; SAXENA, Rohit; SURESH, Juluri; VISWANATHAN, Vellarkad; ZAINUDDIN, Mohd; DHARSHINIS, Akila Parvathy; KRISTAM, Rajenda; WO2015/97122; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, 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 1615-14-1 as follows.

EXAMPLE 50 7-[2-(1H-1-Imidazolyl)ethoxy]-4H-4-chromenone Under N2, a solution of 0.75 g (4.6 mmol) of 7-hydroxy-4H-4-chromenone (J. Med. Chem., 1991;34:248) in 20 mL of THF was treated with 1.21 g (4.6 mmol) of triphenylphosphine and 0.5 g (5.1 mmol) of 2-(1H-1-imidazolyl)-1-ethanol and the solution cooled in ice. This was then treated over 10 minutes with 0.72 mL (4.6 mmol) of diethyl azodicarboxylate, and the solution stirred at room temperature overnight. The solution was diluted with EtOAc, washed twice with H2 O, twice with saturated NaHCO3, and then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. Chromatography on silica gel, eluding with a gradient of CH2 Cl2 to CH2 Cl2 /MeOH (96/4) gave 0.12 g (10% yield) of the product as a pink solid, mp 131-133 C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 257 (M+H+). Calculated for C14 H12 N2 O3 *0.08 CH2 Cl2 (MW 262.76): C, 64.34; H, 4.66; N, 10.66. Found: C, 64.34; H, 4.72; N, 10.66.

According to the analysis of related databases, 2-(1H-Imidazol-1-yl)ethanol, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US6133303; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below.

A mixture of (S)-(+)-2-(diphenylphosphine oxide)-1,1′-binaphthyl-2′-amine 6 (200 mg, 0.426 mmol) and 2-formyl-1H-benzoimidazole (187 mg, 1.278 mmol) in the presence of 4 A MS (0.85 g) in dry toluene (8 mL) was stirred at 110 ¡ãC for 14 h in a pressure tube.

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; Eliseenko, Sviatoslav S.; Liu, Fei; Tetrahedron; vol. 75; 4; (2019); p. 518 – 526;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, 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 288-32-4 as follows.

To imidazole (0.41 g, 6.0 mmol) in CH2CI2 was added bromoacetonitrile (0.21 g, 2.0 mmol), and the reaction was refluxed for 30 minutes. The mixture was cooled to room temperature and filtered, and the filtrate was concentrated to give the desired product.

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

Reference:
Patent; AUTOIMMUNE PHARMA LLC; BENISON, Jeffrey; (157 pag.)WO2018/152405; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. 288-32-4

EXAMPLE 2 Manufacturing of 1-[4-(4-phenylbutylamino)phenyl]imidazole STR22 9.5 g of imidazole were dissolved in 100 ml of DMF, and the resultant solution was further added with 6.1 g of 60% NaH while cooling it with ice. The solution was then stirred for 30 min. and further for 1 hour at room temperature. Then, the solution was added with 20.0 g of 4-chloronitrobenzene and then stirred for 2 hours at a temperature of from 80 to 85 C. The solution reacted was poured into ice water, and the crystals precipitated was filtered and then dried to obtain 22.5 g of 4-(imidazole-1-yl)nitrobenzene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Patent; Nippon Soda Co., Ltd.; US5965743; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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. 33543-78-1.

First step The compound (85) (2.50 g) was dissolved in pyridine (25 ml), trityl chloride (5.47 g) and dimethylaminopyridine (2.40 g) were added, the mixture was stirred at 100¡ãC for 22 hours. Water was added, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography to afford the compound (86) (2.81 g). 1H-NMR (CDCl3), delta: 0.94 (3H, t, J = 7.1 Hz), 3.82 (2H, q, J = 7.1 Hz), 6.97 (1H, d, J = 1.0 Hz), 7.12 (7H, m), 7.28-7.30 (9H, m).

The synthetic route of Ethyl 1H-imidazole-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; EP2305672; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, The chemical industry reduces the impact on the environment during synthesis 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a 3 L 4-neck flask equipped with an overhead stirrer, nitrogen bubbler, and thermocouple was added 5-bromo-1-methyl-1H-imidazole (47.96 g, 297.9 mmol), followed by THF (537 mL). To this room temperature solution was added isopropylmagnesium chloride/lithium chloride complex [1.3 M in THF] (246.8 mL, 320.8 mmol) (addition temperature maintained between 16.6 and 25 C.) to afford a milky suspension and the reaction was stirred for 60 minutes and then cooled to 5.3 C. in an ice bath. To this mixture was added a solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (53.66 g, 229.14 mmol, Intermediate 10: step b) in THF (268.3 mL) (addition temperature between 5.3 and 5.6 C.) to afford an orange mixture. After addition, the reaction was warmed to room temperature over 2 hours. After stirring at room temperature for 18 hours, THF (200 mL) was added and the reaction was stirred for 2 hours. The reaction was then cooled to 4 C. with an ice bath and carefully quenched with 2 N aqueous HCl to pH=7, quenching temperature reached 12 C. The mixture was diluted with ethyl acetate (500 mL), phase split and the organic layer was washed with brine (2*200 mL), dried over sodium sulfate, filtered, and the solvent was removed. Hot ether was added and the suspension was then filtered to afford the title compound as a solid.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, I believe this compound will play a more active role in future production and life. 152628-03-0

Example 1:Orthophosphoric acid (210 gms) was taken in round bottomed flask and Rho205 (210 gms) was added in portions with vigorous stirring. (Note: Sharp increase in temperature > 200 C). The above mass is allowed to cool to 70 C and 2-n-propyl- 4-methyl-benzimidazole-6-carboxylic acid (70 gms, 0.321 mol) was added slowly. Then N-methylbenzene-l,2-diamine hydrochloride (62.3 gms, 0.321 mol) was added in small portions at same temperature and then the temperature was raised to 125-130 C. After completion, reaction was quenched with ice cold water (1 Lt), adjusted pH of the reaction mixture to 9-10 by the addition of aqueous ammonia solution. Obtained solid was filtered and washed with cold water until the pH of the filtrate becomes neutral. Then the crude solid was washed with hot water until colorless filtrate was observed. The crude solid was boiled in ethyl acetate (700 ml) for 2-3 hrs. The reaction mass was cooled and the suspension was filtered off and dried to yield 2-n-propyl-4-methyl-6-(l-methylbenzimidazol-2-yl)-lH- benzimidazole (V) (80 gms, Yield : 82 %).

The chemical industry reduces the impact on the environment during synthesis 152628-03-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; OGENE SYSTEMS (I) PVT LTD; LAKKOJU, Chakrapani; KONETI, Naga Raju; KOKKALLA, Sridhar; MALLELA, Sambhu Prasad Sarma; BOYAPATI, Nanoranjan Choudary; WO2012/28925; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(3-chloropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (193) (320 mg, 0.79 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (127.3 mg, 0.87 mmol), DIPEA (0.32 ml, 2.0 mmol) and MgSQ (300 mg) in MeOH (20 ml) at room temperature for 16 h, followed by addition of NaBh (60 mg, 1.59 mmol) gave the title compound (191 mg, 52percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.18 (s, 1 H), 8.72 (t, J = 5.6 Hz, 1 H), 8.49 (dd, J = 4.7, 1.3 Hz, 1 H), 7.95 (dd, J = 8.1 , 1 .3 Hz, 1 H), 7.54 (s, 1 H), 7.46 (s, 1 H), 7.38 (dd, J = 8.1 , 4.7 Hz, 1 H), 7.17- 7.09 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H), 3.98 (d, J = 4.1 Hz, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (q, J = 6.1 , 5.3 Hz, 2H, 2.74 (s, 1 H) HPLCMS (Method C): [m/z]: 461 [M+H]+

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

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, 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. 312-73-2

The 2 – trifluoromethyl – 1H – benzimidazole 2 (1.35g, 10mmol) added to the is provided with a 15 ml round bottom flask in acetone, stirring to dissolve into the ene (alkyne) propyl bromide (0.87 ml, 10mmol) and K2CO3(2.07g, 15mmol), heating to reflux, TCL detection, after the reaction is complete, cooling, filtering to remove the solid, dichloromethane is used for washing the solid, acetone solution concentration after mixing with the dichloromethane solution, H for2O washing (15 ml ¡Á 3), organic phase with anhydrous MgSO4Drying, filtering the concentrated to obtain the crude product. To obtain 1 – allyl -2 – trifluoromethyl – 1H – benzimidazole (3) 2.10g, yield 94.34%.aceo

Statistics shows that 312-73-2 is playing an increasingly important role. we look forward to future research findings about 2-(Trifluoromethyl)-1H-benzo[d]imidazole.

Reference:
Patent; Zhejiang University of Technology; Zhu, Bingchun; Wang, Yuguang; Dong, Huichan; (15 pag.)CN104496976; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem