Imidazoles-derivatives

The chemical industry reduces the impact on the environment during synthesis 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, I believe this compound will play a more active role in future production and life. 2849-93-6

At room temperature,3.0 g (18.6 mmol) of 1H-benzimidazole-2-carboxylic acid was placed in a 100 mL eggplant type flask,Add 30mL of thionyl chloride, 79 reflux reaction 4h, after the end of the reaction evaporated solvent.Add 30mL ammonia water, 70 reaction 5h, cooling the reaction solution,Filtration of yellow solid, dry. The yield was 55%.

The chemical industry reduces the impact on the environment during synthesis 2849-93-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 288-32-4, name is 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. 288-32-4

To a slightly yellow homogeneous solution of imidazole (5.000 g; 73.444 mmol) in dioxane (135 ml) and distilled water (135 ml) was added successively, at rt (in one portion), sodium carbonate (35.029 g; 330.500 mmol), and iodine (61.515 g; 242.366 mmol). The resulting brown heterogeneous reaction mixture was further stirred at rt, under nitrogen, for 24h. EA (250 ml) was then added followed by an aq. solution of sodium thiosulfate (22.50 g Na2S2O3 in 150 ml of water). The yellow homogeneous organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give the crude product 2, 4, 5-triiodo-1 /-/-imidazole as a yellow solid which was further dried under HV (32.700 g; 100%). LC-MS: tR = 0.78 min.; [M+H]+ = 447.03 g/mol.

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 288-32-4.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/78291; (2008); A1;,
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 3034-50-2 as follows. 3034-50-2

1H-Imidazole-4-carbaldehyde (45.2g, 0.47M) and acetonitrile (0.8 liter) are introduced into a 2 liter flack and cooled to 8C, then TRT-Cl (13 lOg, 0.47M) was added at 8C and TEA (57.lg, 0.56M) was added dropwise during 20 mm. The reaction mixture was stirred at 8 to 18C for 2 hrs.The reaction mixture was poured into a stirring mixture of water (0.72 liter) and MTBE (0.72 liter) and stirred for 10 minutes. The resulting solid was isolated by filtration on Buchner funnel and dissolved with THF (3 liter). The solution was dried over Na2504 and concentrated to remove most of the solvent.MTBE (400 ml) and PE (200m1) was added to the residue, the mixture stirred at 8C for 16 hrs. The precipitated solid was isolated by filtration on Buchner filter and dried in air for 16 hrs at room temperature. Then the filter cake is dried by azeotropic drying with 2-Me-THF (2×500 ml) to give 129g of intermediate 2 as white solid with a yield of 66.5%.

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CLEXIO BIOSCIENCES LTD.; FRENKEL, Anton; IOFFE, Vladimir; (54 pag.)WO2020/16827; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, A common compound: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 141-Methyl-N-[3-methyl-5-(trifluoromethoxy)benzyl]-N-(tetrahydro-2H-thiopyran-4-yl)-1H-imidiazole-4-carboxamideA mixture of N-[3-methyl-5-(trifluoromethoxy)benzyl]tetrahydro-2H-thiopyran-4-amine (830 mg), 1-methyl-1H-imidazole-4-carboxylic acid (380 mg), EDC.HCl (860 mg), HOBt (460 mg), dimethylformamide (20 mL) and triethylamine (0.94 mL) was stirred overnight at room temperature.The solvents were distilled off under reduced pressure and extraction was conducted with ethyl acetate; the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and dried over anhydrous magnesium sulfate.After filtering off the desiccant, the solvent was concenrated.The residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=90:10 to 10:90) to give the titled compound (810 mg).

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-imidazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2012/10414; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, Name is 5-Iodo-1H-imidazole, 71759-89-2, 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.

Step D 1-Trityl-4-iodoimidazole Trityl chloride (3.8 g, 13.6 mmol) was added to a cooled (0 C.) solution of 4-iodoimidazole (2.25 g, 11.6 mmol) and triethylamine (2 ml, 14.3 mmol) in methylene chloride (25 ml). After stirring for 30 min the reaction mixture was warmed to room temperature and stirred ther for 2 h. The reaction mixture was washed well with water and saturated NaHCO3 then dried (Na2 SO4). Concentration gave the product as a white solid. 1 H NMR (CDCl3) d 6.92 (s, 1 H), 7.08-7.20 (m, 6 H), 7.28-7.40 (m, 10 H).

Statistics shows that 5-Iodo-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-89-2.

Reference:
Patent; Merck & Co., Inc.; US5932606; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

705-09-9, Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-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 705-09-9.

Step 2: NaH (60%, l . lg, 45.8mmol, 1.5eq) was added protion-wise to a solution of compound Id (3.4g, 20.1mmol, l .leq) in DMF(50mL) at 0C and the mixture was stirred at r.t for 45min. Compound 5a (5.0g, 18.3mmol, leq) was added to the mixture. The mixture was stirred at r.t over weekend. Water was added and the mixture was extracted with ethyl acetate, the organic layer was washed with water for 3 times, dried, concentrated and purified by column chromatography to give 5b (3.4g, yield: 45.8%) as a white solid.’H NMR(CDC13, 300MHZ, ppm): delta 10.23(s, 1H), 7.72(d, 1H), 7.54(d, 1H)ES-MS m/z: 321(M+H+).

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; WO2011/41399; (2011); 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

2-Trifluoromethyl-1H-benzimidazole 2 (1.35 g, 10 mmol)Was added to a round bottom flask equipped with 15 mL of acetone,After stirring, an alkene (alkyne) propyl bromide (0.87 mL, 10 mmol)And K2CO3 (2.07 g, 15 mmol),Heating reflux,TCL detection,After the reaction is complete,Cooling cooling,The solid was removed by filtration,The solid was washed with dichloromethane,The acetone solution was concentrated and mixed with the dichloromethane solution,Washed with H2O (15 mL x 3),The organic phase was dried over anhydrous MgSO4,Filtered and concentrated to get crude,To obtain 2.06 g of 1-propargyl-2-trifluoromethyl-1H-benzimidazole (3)Yield 91.96%.

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; Wang Yuguang; He Rongjun; Dong Huichan; Zhu Bingchun; (14 pag.)CN104496975; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, 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. 288-32-4 name is 1H-Imidazole, 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 N-H heterocycle (1 mmol) and aryl halide (2 mmol) in toluene were added catalyst (0.07 g, 0.016 mmol) and K2CO3 (276 g, 2 mmol) and the mixture stirred at 110 C for the specified time. The progress of the reaction was monitored by TLC. The reaction mixture allowed cooling to room temperature and ethyl acetate (25 mL) was added and the mixture stirred for 15 min to ensure product removal from catalyst. Then the catalyst was filtered, washed with ethyl acetate (2 9 25 mL). The organic layer was evaporated under vacuum on a rotary evaporator and the crude product was obtained. Further purification was achieved by column chromatography using ethyl acetate/n-hexane gradient. Structural assignments of the products are based on their 1H NMR and melting point.

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

Reference:
Article; Hosseinzadeh, Rahman; Aghili, Nora; Tajbakhsh, Mahmood; Catalysis Letters; vol. 146; 1; (2016); p. 193 – 203;,
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 7098-07-9 as follows. 7098-07-9

General procedure: To a vigorously stirred solution of imidazole derivatives (23.39mmol) in dry toluene (10mL) at room temperature was added the solution of chloromethyl-salicylaldehydes 2a, b (19.50mmol) in dry toluene (10mL), drop-wise, under nitrogen atmosphere. The resulting solution was further stirred at 60¡ãC for 24h. The product separated out was washed twice with toluene (2¡Á5mL) and several times with ether (5¡Á10mL), to remove the unreacted materials, and dried under vacuum to give pale yellow solid which used for the following preparations without further purification. Samples of the products were nevertheless isolated and fully characterized, as described below.

According to the analysis of related databases, 7098-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elshaarawy, Reda F.M.; Janiak, Christoph; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 31 – 42;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 26663-77-4, name is Methyl benzimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 26663-77-4

tert-butyl-2-chloro-4-fluorobenzoate (200 mg, 0.867 mmol), methyl lH-benzimidazole-5- carboxylate (214 mg, 1.214 mmol) and potassium carbonate (359 mg, 2.60 mmol) in dry acetonitrile (12 mL) was stirred at 85C for 6 h. The reaction mixture was cooled to RT and the solid was filtered and washed with EtOAc. The filtrate was concentrated and purified by flash chromatography (ISCO CombiFlash system, 80g Silica gel column, 0-60% EtOAc in hexane as as eluting solvent) to afford the product as a mixture of two regioisomers. Further separation of this mixture of products by SFC technique on chiral AD-H column and using 55% MeOH/C02 as mobile phase yielded compound 18A-a, methyl l-(4-(tert-butoxycarbonyl)-3-chlorophenyl)- lH-benzo[d]imidazole-6-carboxylate, and compound 18A-b, methyl l-(4-(tert-butoxycarbonyl)- 3- chlorophenyl)-lH-benzo[d]imidazole-5-carboxylate. For compound 18A-a: methyl 1 -(4-(tert-butoxycarbonvD-3 -chlorophenvD- 1 H- benzo[dlimidazole-6-carboxylate (M+H) calc. = 387.10; found = 387.15. 1H NMR (500 MHz, CD3OD): delta 8.70 (s, br, 1 H); 8.30 (s, br, 1 H); 8.08 (dd, J = 1.5 Hz, J = 8.5 Hz, 1 H); 8.01 (d, J = 8.5 Hz,l H); 7.89 (d, J = 2.5 Hz,l H); 7.86 (d, J = 8.5 Hz, 1 H); 7.74 (dd, J = 2.0 Hz, J = 8.5 Hz, 1 H); 3.95 (s, 3H); 1.66 (s, 9H) For compound 18A-b: methyl 1 -(4-(tert-butoxycarbonyl)-3 -chlorophenyD- 1 H- benzo[dlimidazole-5-carboxylate (M+H) calc. = 387.10; found = 387.15. 1H NMR (500 MHz, CD3OD): delta 8.56 (s, br, 1 H); 8.47 (s, br, 1 H); 8.12 (dd, J = 1.5 Hz, J = 8.5 Hz, 1 H); 8.10 (d, J = 8.5 Hz,l H); 7.89 (d, J = 2.0 Hz,l H); 7.76 (d, J = 8.5 Hz, 1 H); 7.73 (dd, J = 2.0 Hz, J = 8.5 Hz, 1 H); 3.97 (s, 3H); 1.65 (s, 9H) Additional NMR studies (NOE) confirmed the structure assignments of the two products.

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, 26663-77-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem