Month: August 2021

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

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. 31722-49-3, name is 1H-Imidazole-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31722-49-3

Compound 234.2. 5-Iodo-lH-imidazole-2-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution lH-imidazole-2-carbonitrile (compound 234.1, 3.39 g, 36.42 mmol) in sodium hydroxide (54.7 mL, 2 M). Iodine (9.26 g, 36.46 mmol) was added to the reaction. The reaction mixture was stirred for 5h at room temperature. The pH of the solution was adjusted to 5 with HCl (2 M). The aqueous phase was extracted with 3 x 80 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/1.5) as eluent to furnish 1.02 g (13%) of the title compound as a white solid.

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:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Iodo-1-trityl-1H-imidazole

4-iodo-1-trityl-1H-imidazole (38.7 g, 88.8 mmol), (2-formylphenyl)boronic acid (20.0 g, 133 mmol)And K3PO4 (56.4 g, 266 mmol) was dissolved in 1,4-dioxane (300 mL) and water (60 mL).Nitrogen gas was bubbled through the reaction solution for 5 min, then Pd(PPh3)4 (5.12 g, 4.44 mmol) was added, and the reaction mixture was bubbled with nitrogen for 5 min.The reaction was heated at 90 C for 16 h under nitrogen.After the reaction was completed, the temperature was lowered, and the celite was filtered, and the filtrate was diluted with water (100 mL) and EA (300 mL), and the mixture was allowed to stand for separation. The aqueous phase was extracted with EA (300 mL×2; combined organic phase, water (100 mL) and saturated brine (100 mL × 3) washing.The organic phase was concentrated under reduced pressure to give a residue.Purified with PE/EA=3/1 column,Obtained a light brown viscous oil 2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (15.0 g, 40.8%).

The synthetic route of 96797-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Weixin Biological Technology Co., Ltd.; Yu Jindi; Lu Xianping; Li Zhibin; Xin Lijun; Zhu Jiangfei; Fu Chao; (67 pag.)CN108203438; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 96797-15-8,Some common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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 suspensionof 4 (3.0 g, 6.9 mmol), the appropriate 2-formyl boronic acid(1.6 g, 10.7 mmol) and K3PO4 (4.4 g, 20.8 mmol) in DMF (30 mL) andwater (6 mL) was purged with nitrogen for 5 min, followed by theaddition of Pd(PPh3)4 (0.6 g, 0.5 mmol) and the mixturewas purgedwith nitrogen for another 5 min. The reaction mixture was stirredat 90 C for 16 h under an atmosphere of N2. The solution wasallowed to cool and was filtered through a plug of celite. Themixture was diluted with water (50 mL) and was extracted withethyl acetate to afford the crude product which was purified byflash column chromatography on silica gel to yield 6 as a white solid(1.9 g, 66.7%). Mp 147e149 C. 1H NMR (300 MHz, Chloroform-d)d(ppm) 7.97 (dd, J 7.8, 1.4 Hz, 1H), 7.72e7.54 (m, 3H), 7.38 (h,J 3.2 Hz,11H), 7.25e7.19 (m, 6H), 7.07 (d, J 1.3 Hz, 1H). MS (EI) m/z 415.2 [MH].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-trityl-1H-imidazole, its application will become more common.

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

Reference of 13570-08-6, 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. 13570-08-6 name is 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, 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 stirred solution of compound 80 (tosyiate) (536 mg, 1.36 mmol), compound 79 (200 mg, 1. 13 mmol) and HOBt (230 mg, 1.70 mmol) in 5 mL DCM, was added DIPEA (0.99 mL, 5.7 mmol) drop-wise and stirred at 0 C for 10 min under inert atmosphere. Then EDC-HC1 (283 mg, 1.48 mmol) was added to the reaction mixture and allowed to stir at room temperature for 16 h. After completion [confirmed by TLC (70% EtOAc-Hexane, Rf-0.4) and LC-MS] reaction mixture was partitioned between water (70 mL) and DCM (3×60 mL). Organic layer was separated, dried (MgSCfi) and concentrated. Resultant crude was purified by column chromatography (eluent: 30-65% EtOAc-hexane, S1O2) to yield compound 81 (210 mg, 48.8%) as white solid. Mass [ESI]: m/z. 379.45 [M++l]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; CYTOSITE BIOPHARMA INC.; BILCER, Geoffrey, Malcolm; KELLY, Terence, Alfred; (190 pag.)WO2019/160916; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7098-07-9,Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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: A generic experimental procedure is described: N-substituted imidazoles 1-6 (1 mmol equivalent) and 2,6-bis(chloromethyl)pyridine 7 (0.5mmol equivalent for each compound, m.p 73-78 °C; ALDRICH) were mixed together under inert condition in a 50 ml round bottom flask with gentle stirring. The temperature was then gently raised to 60 °C; giving a molten substance that was allowed to continue stirring for 16 h at 60 °C. The resultant grey or light brown crude solid was allowed to cool to room temperature and loaded onto a short plug of silica. Unreacted starting materials are rinsed-out with ethyl acetate while the salts were obtained (Rf value 0.01) as methanol (100percent) eluents. Solvent is then removed under reduced pressure to yield pure imidazolium salts 8-13.

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

Reference:
Article; Ibrahim, Halliru; Bala, Muhammad Dabai; Tetrahedron Letters; vol. 55; 46; (2014); p. 6351 – 6353;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39513-26-3, These common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, 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.

5-bromo-1,3-dihydro-2H-benzo[d]imidazol-2-one (50 mg, 0.235 mmol), 20 (124 mg, 0.352 mmol), and Pd(PPh3)4 (14mg, 5 mol%), were combined in a microwave vial and flushed with N2 for5 min. Dioxane (3 mL) and aq. K3PO4 (1 M, 0.5 mL) wereadded and the mixture was heated in a Biotage microwave at 100 C for 1 h. H2O(3 mL) and EtOAc (7 mL) were added and the organic layer was separated, driedusing Na2SO4 and evaporated. Gilson HPLC purificationafforded 22 (1.44 mg, 2%).

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lotesta, Stephen D.; Marcus, Andrew P.; Zheng, Yajun; Leftheris, Katerina; Noto, Paul B.; Meng, Shi; Kandpal, Geeta; Chen, Guozhou; Zhou, Jing; McKeever, Brian; Bukhtiyarov, Yuri; Zhao, Yi; Lala, Deepak S.; Singh, Suresh B.; McGeehan, Gerard M.; Bioorganic and Medicinal Chemistry; vol. 24; 6; (2016); p. 1384 – 1391;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem