Author: Jessica.F

Synthetic Route of 51605-32-4,Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

and also, starting from 4-methylimidazole-5-carboxylic acid ethyl ester, 1-(2,6-difluorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 59°-61° (from hexane) and 1-(2,6-difluorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 107°-108° (from toluene/ether), 1-(o-chlorobenzyl)-4-methylimidazole-5-carboxylic acid ethyl ester, m.p. 74°-76°, and 1-(o-chlorobenzyl)-5-methylimidazole-4-carboxylic acid ethyl ester, m.p. 100°-104°; and also, starting from imidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 71°-73° (from petroleum ether), 1-(o-chlorobenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester, m.p. 69°-70° (from ether/hexane) and 1-(o-methylbenzyl)-imidazole-4,5-dicarboxylic acid diethyl ester (oil); and also, starting from 2-methylimidazole-4,5-dicarboxylic acid diethyl ester, 1-(2,6-difluorobenzyl)-2-methylimidazole-4,5-dicarboxylic acid diethyl ester, m.p. 63°-64° (from ether/hexane).

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4851424; (1989); A;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

(1) potassium carbonate K2CO3 , AMST-1 C12H20N2O3 , AMST-2 C33H25BrN4 , In acetonitrile is added to the reaction kettle, raising the temperature to 80 C, keeps reaction for 3 hours, HPLC monitoring reaction, after the completion of reaction of outer 95 C distilling acetonitrile, lowering the temperature to 0 C stirring 8 hours, filtration products, the filter cake is acetonitrile leaching, after drying, the crude product in water for 3 C beating 5 hours to remove the inorganic salt, filtered, washed with water, 90 C drying to constant weight to obtain the product AMST – 3 C45 H44 N6 O3 ; K the potassium carbonate2 CO3 , AMST-1 C12H20N2O3 , AMST-2 C33H25BrN4 , Acetonitrile and water mass ratio of the 173:150: 383:2000: 1600;

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Yong Tong Technology Co., Ltd.; Liu Zhongchun; (10 pag.)CN107311989; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

A solution containing the product from step 1 (8.36g, 54.2 mmol) and 2-amino-4- nitrophenol (8.74g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.Og), as a yellow solid. MS (ESI) m/e (M+H4): 180. 1H NMR (DMSO) delta: 7.85 ~ 7.96(m, 3 H), 7.52(d, J = 8.8 Hz, 1H).

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

(1) 0.84 g (5 mmol) of 2-difluoromethylbenzimidazole dissolved in DMF (25 ml) was added and reacted with 60% sodium hydride (0.24 g, 6 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 2,4,6-trichloropyrimidine (0.92 g, 5 mmol) dissolved in DMF (25 ml) and stirred at room temperature for 1.5 hours. The reaction solution was poured into water and the resulting precipitates were recrystallized from methanol to obtain 0.98 g (yield: 62%) of 4,6-dichloro-2-(2-difluoromethylbenzimidazol-1-yl)pyrimidine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; ZENYAKU KOGYO KABUSHIKI KAISHA; EP1389617; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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 870837-70-0, category: imidazoles-derivatives

Cyano ethyl acetate (76.0 muL) and piperidine were added one by one to an ethanol solution (5.0 mL) of 4-(1H-imidazol-1-yl-3-methoxybenzaldehyde (144 mg) obtained in Example 111 (35.0 muL). The reaction solution was refluxed for 3.5 hours, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude ester product

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; Eisai Co., Ltd.; US2006/4013; (2006); 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 51605-32-4 as follows. COA of Formula: C7H10N2O2

(5-Methylimidazol-4-yl)methylchloride hydrochloride (14) A paste of ethyl 4-methyl-5-imidazolecarboxylate (37.5 g, 0.243 mol) and a little dry THF was added in portions to a stirred suspension of LiAlH4 (12.0 g, 0.316 mol) in 1.0 L of dry THF under a flow of nitrogen. After refluxing for 4 h, the suspension was cooled in an ice-water bath and the excess LiAlH4 destroyed with successive additions of 12 mL of H2 O, 12 mL of 15percent NaOH, and 45 mL of H2 O. The white suspension was brought to room temperature (2 h) and filtered. After collecting the precipitate, it was digested in hot THF (500 mL), cooled, and filtered again. The total THF filtrate was concentrated in vacuo, the residual orange oil was dissolved in a minimum amount of EtOH, and 500 mL of hot EtOAc:Et2 O (3:2) was added. The solution was chilled yielding 15.0 g (55percent) of (5-methylimidazol-4-yl)methanol as white prisms: mp 138° (lit. 138°). This material (9.6 g, 0.086 mol) was dissolved in 50 mL of conc HCl and heated on a steam bath for 30 min. The acidic mixture was concentrated in vacuo to dryness and the solid dissolved in a minimum amount of EtOH. With the addition of a little dry Et2 O, 14 (8.5 g, 67percent) precipitated as a white powder: mp 236°-237° (lit. 222°).

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Research Corporation; US4432983; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

Methyl 5-bromo-2-methylthiophene-3-carboxylate (5.5 g, 23.4 mmol) was added to a 250 mL round bottom flask.4-cyclopropyl-1H-imidazole (2.5 g, 23.4 mmol),Cuprous iodide (669 mg, 3.51 mmol),1,10-phenanthroline (1.3 g, 6.56 mmol),Cesium carbonate (15.2 g, 46.8 mmol) and 100 mL of toluene were reacted at 110 C for 20 hours. When the reaction is over,The reaction solution was concentrated, and the residue was applied to silica gel column chromatographyEthyl acetate = 1: 1) to give the desired product 500mg, yield 8.1%.

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wang Tingzhong; (35 pag.)CN110294746; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 88427-96-7,Some common heterocyclic compound, 88427-96-7, name is 4-(2-Methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C11H10N2O, 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.

Working Example 34 4-(6-Chloronaphthanlene-2-sulfonyl)-1-[4-(2-methyl-1H-imidazol-1-yl)benzyl]-2-piperazinone To a solution of N-(tert-butoxycarbonyl)ethylenediamine (431 mg) and 4-(2-methyl-1H-imidazol-1-yl)benzaldehyde (500 mg) in dichloromethane (10 ml) was added acetic acid (323 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, sodium triacetoxyborohydride (855 mg), and the mixture was stirred at room temperature for 15 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was extracted with water, and the aqueous layer was made alkaline with sodium hydroxide solution. The mixture was extracted with dichloromethane and dried with sodium sulfate, and sodium sulfate was filtered off. To the filtrate was added triethylamine (543 mg) and then was added at 0 C. chloroacetyl chloride (455 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with sodium bicarbonate solution and brine, dried and concentrated, and the residue was dissolved in DMF (15 ml). To the solution was added sodium hydride in oil (129 mg), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, dried and concentrated, and the residue was purified with column chromatography (ethyl acetate) to give 4-(tert-butoxycarbonyl)-1-[4-(2-methyl-1H-imidazol-1-yl)benzyl]-2-piperazinone.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6403595; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4,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.

(a) A solution of alpha-bromo-4-tolunitrile (86.6 g) in dichloromethane (1000 mL) is mixed with imidazole (68.0 g). The mixture is stirred at ambient temperature for 15 hours and then diluted with water (1000 mL). Any undissolved solid is removed by filtration and the separated organic solution is then repeatedly washed with water (5*200 mL) to remove excess imidazole, and then dried (MgSO4). The crude product obtained upon evaporation of the solvent can be purified by trituration with cold diethyl ether (200 mL) to obtain 4-(1-imidazolylmethyl)-benzonitrile, m.p. 99-101; HCl salt, m.p. 142-144.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4978672; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1402838-08-7, 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Different substituted ethan-1-one (1 mol equiv.) was added to asolution of NaOEt (attained from Na (2 mol equiv.) dissolved inEtOH (1.4 M) at 0 C), followed by the addition of intermediate 6(1 mol equiv.). The yellow liquid was stirred at room temperaturefor 3 h. The solvent was removed under reduced pressure and thesaturated NH4Cl solution was added to the mixture to quench thereaction. The mixture was diluted with water, and was extractedwith dichloromethane to afford the crude product, which was usedto the next step without any further purification.

The chemical industry reduces the impact on the environment during synthesis 2-(1-Trityl-4-imidazolyl)benzaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem