Author: Jessica.F

Reference of 144689-93-0,Some common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

Example 1; Ethyl 4-( 1 -hydroxy- 1 -methylethyl)-2-propyl- 1 – { 4- [2-(tetrazol-5-yi)phenyl]phenyl}methyl- imidazole-5-carboxylate (3); Acetone (200 ml) was added to the weighed ethyl ester of 4-(l -hydroxy- l-methylethyl)-2- propyl-lH-imidazole-5-carboxylic acid (1; 20 g), substance 2 (46.4 g), potash (40 g), and polyethylene glycol 400 (2 g). The resulting mixture was heated to the boil for H h. After filtering off the solids the filtrate was concentrated, ethanol (350 ml) was added to the concentrated filtrate, and the suspension was heated to the boil. After it was cooled to 15 C (20 minutes), the insoluble portion was sucked off and washed with ethanol (40 ml). After drying (50 0C, in vacuo), 50.7 g of the product (85 %) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, its application will become more common.

Reference:
Patent; ZENTIVA, A.S.; WO2007/48361; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

The imidazole-2-carboxylic acid (10 g, 89.2 mmol) in suspension in thionyl chloride (160 mL) was heated to reflux, under agitation for 18 h. The reaction mixture was cooled, then filtered, washed with toluene, and dried under high vacuum to obtain a yellow solid (yield, 80-85%). M.p.: 164 C. 1H NMR (300 MHz, DMSO-d6) delta: 8.85 (s, 2H); 8.2 (s, 2H). 13C NMR (300 MHz, DMSO-d6) delta: 145.85, 144.95, 125.20, 120.15.

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

Reference:
Article; Moarbess, Georges; Guichou, Jean-Francois; Paniagua-Gayraud, Stephanie; Chouchou, Adrien; Marcadet, Olivier; Leroy, Fiona; Ruedas, Remi; Cuq, Pierre; Deleuze-Masquefa, Carine; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 268 – 274;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14813-85-5, 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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Starting materials 16-18 (1 mmol) and K2CO3 (2 mmol) were suspended in DMF (1.8 mL) and stirred at 25 C for 30 min. 11 and 12, respectively (1.5 mmol) were added after 30 min and the solution was stirred at room temperature overnight. To the mixture was added ethyl acetate (5 mL) and water (5 mL).The aqueous layer was extracted several times with ethyl acetate (10 mL) and the combined organic layers were washed with brine, dried over MgSO4 and evaporated to dryness.

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-Phenyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Neudorfer, Catharina; Seddik, Amir; Shanab, Karem; Jurik, Andreas; Rami-Mark, Christina; Holzer, Wolfgang; Ecker, Gerhard; Mitterhauser, Markus; Wadsak, Wolfgang; Spreitzer, Helmut; Molecules; vol. 20; 1; (2015); p. 1712 – 1730;,
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. 7098-07-9, name is 1-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

The reaction end point was monitored by adding 6.16 g (10 mmol) of M1 ‘, 0.96 g (10 mmol) of 1-ethyl tasteless, 50 mL of acetonitrile at room temperature for 48 h in a dry 100 mL three-necked flask. Washed with petroleum ether (100 mL x 3), the resulting viscous liquid was again Washed with ether (100 mL x 3) to give a yellow solid, Recrystallization from methylene chloride and drying in vacuo for 24 h afforded a pale yellow solid As the target compound (B2), 7.1 g, and the yield was 99percent.

The synthetic route of 7098-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central China Normal University; Zhang Aidong; Zhang Tiejiang; Duan Jiang; Tu Haiyang; (22 pag.)CN107188869; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 57090-88-7, Safety of 1H-Imidazole-4-carbonitrile

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 96797-15-8, 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 96797-15-8 as follows.

A. 5-imidazol-4-yl-2-methoxypyridine. To a solution of 4-IODO-1- TRITYL-LH-IMIDAZOLE (25 g, 57.2 mmoles) in THF (150 ml) at room temperature was added ethylmagnesium bromide (69 ml, 68.7 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (9.4 g, 68.6 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (6.6 g, 5.72 mmoles) and 5-BROMO-2-METHOXYPYRIDINE (8.9 ml, 68.7 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane (500 ml) and washed with a 30% NaOH solution containing an added 20 g of EDTA (3x 200 ml), with NACI (sat. ) (200 ml), dried over MGS04, filtered, and concentrated. To the crude material was added dichloromethane (200 ml) and trifluoroactetic acid (40 ml, 410 mmoles). After standing for 6 hours, the reaction was concentrated and pumped on overnight. The crude material was purified by flash chromatography using 0-5% MEOH/CH2CL2 with 0.1% triethylamine yielding 5-imidazol-4-yl-2- methoxypyridine (7. 0g, 70%). MH+ (176)

According to the analysis of related databases, 96797-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 872-49-1, 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. 872-49-1, name is 5-Chloro-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE IV 4-Chloro-1,3-dimethyl-2-[(2-oxopropyl)thio]-1H-imidazolium chloride STR60 The starting material, 4-chloro-1,3-dimethylimidazoline-2-thione was first prepared by adding dropwise and intimately admixing 5.68 grams (0.04 mol) of methyl iodide to a solution of 4.0 grams (0.0343 mol) of 5-chloro-1-methylimidazole in 25 milliliters of methylene chloride. The resulting mixture was stirred overnight at room temperature whereupon a crystalline product was found to have formed.

The synthetic route of 5-Chloro-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5030644; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 67085-11-4,Some common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

B. Alternatively, a mixture of 1-(4-(4-chlorophenyl)-2-hydroxybutyl)imidazole (1.8 kg, 7.18 mol), 2.25 equivalents of pyridine-sulfur trioxide complex and methylene chloride (8.6 L) stirred in the presence of excess dimethyl sulfoxide (19 L) and triethylamine (9 L) at 20-35 C. for 3 hours. Upon completion of reaction, the mixture was combined with water (76 L) and hexane (34.4 L). The product was isolated, washed with water and hexane and dried to yield 4-(4-chlorophenyl)-1-(imidazol-1-yl)butan-2-one, 1.48 kg (83% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, its application will become more common.

Reference:
Patent; Syntex (U.S.A.) Inc.; US5208331; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of ethyl lH-imidazole-2-carboxylate (10.0 g, 71.4 mmol) [Combi-Blocks, SS-7811] in N,N-dimethylformamide (357 mL) was treated with potassium tert-butoxide (74.9 mL, 74.9 mmol, 1.0 M in tetrahydrofuran) dropwise and stirred at 20 C for 1 h. The reaction mixture was then treated with a solution of 0-(4-nitrobenzoyl)hydroxylamine (13.7 g, 74.9 mmol) in N,N-dimethylformamide (120 mL) dropwise via an addition funnel and stirred at 20 C for 3 h. The reaction mixture was filtered and the solid was washed with acetonitrile. The filtrate was evaporated to give the crude product as a slightly oily red solid that was used without further purification.

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

Reference:
Patent; INCYTE CORPORATION; DOUTY, Brent; BUESKING, Andrew W.; BURNS, David M.; COMBS, Andrew P.; FALAHATPISHEH, Nikoo; JALLURI, Ravi Kumar; LEVY, Daniel; POLAM, Padmaja; SHAO, Lixin; SHEPARD, Stacey; SHVARTSBART, Artem; SPARKS, Richard B.; YUE, Eddy W.; (355 pag.)WO2019/79469; (2019); A1;,
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. 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C19H13BrN2

[0076] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)- lH-benzo[d]imidazole (3): A mixture of compound (2) (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533g, 2.1 mmol), Pd(dppf)Cl2 (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4mmol) in 1,4-dioxane (20 mL) was heated at about 80 C under argon overnight. After cooling to room temperature, the whole was diluted with ethyl acetate (~80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5: 1 to 3:1) to give a white solid (0.64 g, in 81% yield).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; SISK, David, T.; HARDING, Brett, T.; CAYAS, Jensen; LI, Sheng; MOCHIZUKI, Amane; CHAE, Hyun, Sik; KHAN, Sazzadur, Rahman; MA, Liping; BOTTGER, Rebecca; WO2011/34967; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem