Author: Jessica.F

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. Recommanded Product: 1H-Imidazole

General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), Cu2O/nano-CuFe2O4 magnetic composite (0.010 g) and anhydrous DMSO (2 mL) was stirred at 100 C. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and with diluted ethyl acetate and the catalyst was separated by an external magnet from the mixture, washed with acetone, dried in an oven at 80 C for 3 h and re-used for a consecutive run under the same reaction conditions. The combined ethyl acetate layer was washed with water, dried over anhydrous MgSO4, The residue was purified by recrystallization or short column chromatography on silica gel to afford the target products in excellent yield.

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:
Article; Elhampour, Ali; Nemati, Firouzeh; Kaveh, Mahdieh; Chemistry Letters; vol. 45; 2; (2016); p. 223 – 225;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2034-23-3, name is 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, 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 2034-23-3, category: imidazoles-derivatives

Step 1. A mixture of 5-chloro-lH-benzo[d]imidazol-2(3H)-one (200 mg, 1.19 mmol), cesium carbonate (850 mg, 2.61 mmol) and tert-butyl 2-bromoacetate (0.37 mL, 2.5 mmol) in acetone (10 mL) was sealed and heated in an oil bath at 65 C for 6 h. The reaction mixture was filtered and concentrated in vacuo, taken up into DCM (20 mL), washed with 5% citric acid and brine, dried over MgSCn, filtered and concentrated in vacuo. The residual solid was recrystallized from 2: 1 hexanes-EtOAc (10 mL) to afford di-tert-butyl 2,2′-(5-chloro2-oxo-lH-benzo[d]imidazole-l,3(2H)-diyl)diacetate (160 mg) as a white solid. LC-MS retention time = 1.38 min; m/z = 285.1 [M-2(t-Bu)+H]+. (Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7^m-particles; Solvent A = 100% Water/ 0.05% TFA; Solvent B = 100% Acetonitrile/0.05% TFA; Flow Rate = 0.8 mL/min. Start % B = 2; Final % B = 98; Gradient Time = 1.5 minutes; Wavelength = 220 nm).

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

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 540516-28-7, 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. 540516-28-7, name is 2-(Hydroxymethyl)-5-bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N-Methyl-2-methanol 5-bromobenzimidazole 50 was prepared according to the procedure by Gonzlez-Chvez et al. [28]. A solution of 5-bromo-(1H-benzimidazole-2-yl)-methanol 28 (0.60 g, 2.60 mmol), and sodium hydroxide (0.10 g, 2.60 mmol) were stirred in dry acetone (10 mL) for 30 min. Then, iodomethane (0.37 g, 2.60 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl. The solid was washed with water (100 mL) and purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (50) as a bright yellow crystals Yield 16%.

The synthetic route of 2-(Hydroxymethyl)-5-bromobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

623577-60-6, name is 4-Bromo-1-isopropyl-1H-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. Product Details of 623577-60-6

A mixture of methyl 5-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine-2- carboxylate (300 mg, 1.08 mmol), 4-bromo-l -(propan-2 -yl)-lH-imidazole (307.0 mg, 1.62 mmol), Pd(PPh3)4 (250.2 mg, 0.22 mmol), K2CO3 (448.8 mg, 3.25 mmol) in dioxane (5 ml) was stirred at 100 C under nitrogen atmosphere overnight. The resulting mixture was 39 concentrated under vacuum and purified by reverse phase flash chromatography with 0-37% MeCN/fhO to afford compound 23-a (180 mg, 64.12%) as yellow oil.

The synthetic route of 623577-60-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WANG, Guoqiang; SHEN, Ruichao; GRANGER, Brett; HE, Jing; XING, Xuechao; HE, Yong; LONG, Jiang; MA, Jun; WANG, Bin; OR, Yat, Sun; (99 pag.)WO2019/213244; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 144689-93-0, 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 144689-93-0 as follows.

First, alkyl 4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylate (20.0 g, 83.2 mmol) and sodium hydroxide powder (6.6 g, 165.0 mmol) were dissolved in 100 ml of acetone and distilled water, and the mixture was stirred and refluxed at 110 C for 3 hours. After cooling to room temperature, the acetone was removed by concentration under reduced pressure. The distilled water layer was titrated with 5N HCl acid at 0C. The solids were filtered off and dried to give compound 2 (14.46 g, 82%).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTC Bio Co.,Ltd; Oh, Chang Hyun; Kim, Jung Hoon; Yu, Sung Won; Kim, Hyun Ir; (9 pag.)KR101628758; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 18075-64-4,Some common heterocyclic compound, 18075-64-4, name is 1-Phenyl-1H-imidazole-4-carboxylic acid, molecular formula is C10H8N2O2, 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 185 Synthesis of 1-Phenyl-1H-imidazole-4-carboxylic acid {2-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide DIPEA (170 mg, 1.3 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid (55 mg, 0.29 mmol) in DMF (5 mL) followed by HOBt (43 mg, 0.32 mmol) and EDCI (140 mg, 0.7 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (98.5 mg, 0.32 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by washing with ether to afford 63.5 mg (49.6% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-[4-(2,5-difluoro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 441.17. 1H NMR (300 MHz, DMSO-d6): delta 8.4 (s, 1H), 8.3 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6 (t, 2H), 7.44 (t, 1H), 7.3 (m, 1H), 6.84 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 4.0 (bs, 1H), 3.8 (bs, 1H), 3.7 (bs, 2H), 3.5 (bs, 1H), 2.1 (t, 2H), 1.8 (d, 2H).

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

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-22-5, 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. 934-22-5, name is 6-Aminobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2,3-di-bromo-6-hydroxy-5-methoxybenzaldehyde (0.1g, 0.32 mmol), 5-amino-benzimidazole (0.03g, 0.21 mmol) and isoamyl alcohol (2 mL) and N2It was stirred at room temperature.It was added dropwise acetic acid (0.07 mL) and the mixture was refluxed overnight.Filtering the reaction mixture, CH2Cl2and dried and then washed with MeOH, the orange powder obtained in26to give a (0.06g, 0.14mmol, 65.4%).

The synthetic route of 6-Aminobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yonsei University Industry-Academic Cooperation; Sungkyunkwan University Academic Cooperation; Lee, Sung Taek; Noh, Kyung Tae; Sim, Hyun Jae; Jung, Young Hoon; Yang, Hey Lan; (34 pag.)KR101639289; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 9; PREPARATION OF A CUCURBITURIL TRIMER HAVING A RIGID ASSMEBLING UNIT; An exemplary pathway for preparing a cucurbituril trimer having a rigid assembling unit, according to the present invention, is presented in Figure 25. Coronene-1,2, 5,6, 9, 10-HEXANE (Figure 25, Compound 41), a derivative of coronene, is reacted with urea, so as to afford an assembling unit which includes three glycolurils units fused therein. The assembling coronene unit is then reacted with glycoluril, Compound 2, in a 1: 15 ratio, and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby obtain the rigid derivatized cucurbituril trimer (Figure 25, Compound 42).

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, Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15108-18-6, 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. 15108-18-6, name is 2-Hydrazinyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-hydrazinobenzimidazole (750 mg;5mmol) in a mixture of 10mL of water and 0.75mL of concentrated HCl was gradually added 1,1,3,3-tetramethoxypropane(820mL; 5mmol). The resulting mixture was heated at reflux for 2 h, then was allowed to cool and filtered.The filtrate was neutralised with solid potassium carbonate,causing the product to precipitate as a pale tan solid, which was filtered and dried in vacuo. Yield 650mg (71%). m.p. 233-2358C; dH(500MHz, d6-DMSO) 6.66 (m, br, 1H,H2), 7.19-7.21 (m, 2H, H6 H7), 7.46 (d, 1H, J 6.1 Hz,H5), 7.58 (d, 1H, J 7.7 Hz, H8), 7.94 (d, 1H, J 1.5 Hz,H3), 8.59 (d, 1H, J 2.9 Hz, H1), 13.10 (s, br, 1H, H4);dC(125MHz, d6-DMSO) 109.2, 111.6, 118.4, 122.2, 122.5,129.1, 133.7, 141.7, 142.9, 146.1; m/z (HR-ES-MS)185.0821 ([M H], calculated for C10H9N4 185.0822);y max(KBr)/cm21 2943m br, 1628m, 1574s, 1479m, 1460s,1387m, 1324m, 1273m, 1226m, 1076s, 927s, 740s.

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

Reference:
Article; Hawes, Chris S.; Kruger, Paul E.; Supramolecular Chemistry; vol. 27; 11-12; (2015); p. 757 – 771;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. Recommanded Product: 1-Methyl-1H-imidazole-2(3H)-thione

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem