Tag: M.W=200-300

Reference of 1964-77-8, A common heterocyclic compound, 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole, molecular formula is C8H7BrN2, 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.

STEP 1 :[00224] To 5-bromo-2-methylbenzimidazole (38 g, 180 mmol) in THF (400 mL) was added di-/ert-butyl dicarbonate (39 g, 189 mmol). The reaction mixture was stirred at room temperature for 24 h and then concentrated. Ethyl acetate (400 mL) was added to the residue, and the solution was washed with 10% aqueous citric acid (2 x 100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (gradient 20-30% ethyl acetate in hexane) provided 1 , 1 -dimethylethyl 6-bromo-2- methyl- lH-benzimidazoie-l -carboxylate (27 g, 48% yield) as a beige solid. MS (EI) for Ci3H,5BrN202: 312 (MH+).

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; EXELIXIS, INC.; RICE, Kenneth; WO2012/71501; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 28890-99-5, These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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.

Intermediate compound 1: (E)- 1 ,3-dibromo-2-(4- methoxystyryl)benzene is synthesized starting from the formation of phosphonium salt with 1,3-dibromo-2-(bromom- ethyl)benzene and triphenylphosphine, followed by Wittig olefination with 4-methoxybenzaldehyde. 1 then undergoes hydrogenation to afford 1 ,3-dibromo-2-(4-methoxyphen- ethyl)benzene, whereby the methoxy sub stituent is deprotected to give phenol derivative intermediate compound 2. Intermediate compound 2 is treated with standard palladium catalyzed reaction conditions to form diaryl ether 3 from intramolecular C-O cross-coupling using known methods (Journal of the American Chemical Society 2011, 133, 9282-92 85, which is incorporated by reference herein in its entirety). 3, together with 1 ,3-dibromobenzene and dichlorodiphenylsilane, undergoes lithiation with n-butyllithium to afford intermediate compound 4. Inventive host compound 5 is then synthesized by a cross-coupling reaction between4 and 5H-benzo[d]benzo[4,5]imidazo[1 ,2-a]imidazole under standard l3uchwald-Hartwig amination reaction conditions.

Statistics shows that 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole is playing an increasingly important role. we look forward to future research findings about 28890-99-5.

Reference:
Patent; Universal Display Corporation; Wolohan, Peter; Drennan, Diana; Fitzgerald, George; (171 pag.)US2018/315942; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3543-73-5, 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. 3543-73-5 name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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.

Example 1 :Preparation of lH-benzimidazol-l-methyI-5-N,N-di(2-hydroxyethyl)-2-butanoic acid ethyl esterlH-Benzimidazol-l-methyl-5-amino-2-butanoic acid (50 gm), water (285 ml) and acetic acid (80 ml) were added at room temperature. The solution was then cooled to 0 to 5C under stirring and ethylene oxide gas was passed in the reaction till the reaction mixture weight increases to 60 gm. The reaction mass was maintained for 1 hour at 0 to 5C and then temperature allowed to room temperature. The reaction mass was maintained for 30 hours at room temperature and then added water (2000 ml) and dichloromethane (2000 ml). To the reaction mass was added sodium bicarbonate (230 gm) and then the layers were separated. The aqueous layer was extracted with dichloromethane. The organic layers were combined and the solvent was distilled off under vacuum to obtain a residual solid. To the residual solid was added hexane (400 ml) and stirred for 30 minutes at room temperature. The solid obtained was collected by filtration, washed with cyclohexane and then dried at 35 to 40C for 2 hours 30 minutes to obtain 63 gm of lH-benzimidazol-l-methyl-5-N,N-di(2-hydroxyethyl)-2-butanoic acid ethyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, and friends who are interested can also refer to it.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; VAMSI KRISHNA, Bandi; WO2012/176214; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1450-93-7, 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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 5-methylfuran-2-carbaldehyde (200 mg, 2 equiv.), 2- aminoimidazole hemisulfate (240.1 mg, 1 equiv.) and TEA (281 pL, 2.2 equiv.) in dichloromethane (6 mL) was added Ti(/PrO)4 (619.5 mg, 2.4 equiv.) and the mixture was stirred at room temperature for 16 hours. Volatiles were evaporated. The concentrated mixture was dissolved in MeOH (6 mL) and NaBH4 (172 mg, 5 equiv.) was added portionwise every 30 minutes until almost complete conversion to the wanted amine. The reaction mixture was transferred to a separatory funnel containing NaHCCf (15 mL), and extracted with DCM (2x 15 mL). The combined organic extracts were dried over Na2S04, were filtered, and the solvent was removed in vacuo to yield the crude product (222 mg). LCMS: MW (calcd): 177.20; MS (ES+, m/z)·. 178.08 [M+H]+.

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, 1H-imidazol-2-amine sulfate(2:1), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E-THERAPEUTICS PLC; POLJAK, Tanja; MODRIC, Marina; VADLAMUDI, Srinivasamurthy; STUBBERFIELD, Colin; (0 pag.)WO2019/229464; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

Add 2-ester benzimidazole (0.5 mmol) and 5-chloro-2-bromobenzaldehyde (0.6 mmol) to the dry Schlenk tube, evacuate nitrogen, and add piperidine (0.05 mmol), 1, 4-Dioxane (2 ml), and the reaction was stirred at room temperature for 3 hours. At room temperature, CuI (0.05 mmol) K2CO3 (1 mmol) and 1,10-phenanthroline (0.1 mmol) were added to the reaction system, and then the mixture was heated to 90 C. and stirred for 8 hours. After stopping the reaction, 15 ml of CH2Cl2 was added to the reaction system, filtered through a sand funnel, and washed with CH2Cl2 three times. The filtrate and washing solution were combined, dried over anhydrous Na2SO4, and concentrated and separated by silica gel column chromatography (eluent: ethyl acetate). Ester: dichloromethane = 30: 1) to obtain the pure product. The material was a yellow solid with a yield of 37%.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Zhou Bingwei; Lu Lulu; Bao Hanyang; (18 pag.)CN110872288; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 14741-71-0,Some common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

Step P: Preparation of 1H-benzo[d]imidazole-2-acethydrazide 15 g 1H-benzo[d]imidazole-2-acetic acid ethyl ester (0.074mol), 100 mL anhydrous ethyl alcohol and 37 mL of 80% hydrazine hydrate were added to a three-necked bottle and reacted under reflux for 4 hours. A white solid was isolated. After sucking filtration, the filter cake was washed with ethanol. After drying, 10.7 g white solid was obtained. Yield: 76%, MS: 191(M+1).

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

Reference:
Patent; Shenyang J & Health Pharmaceutical Co., Ltd.; EP2468730; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

Example 2; Recrystallization of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I from IPA/waterA 50 mL flask was charged with 1 g of the compound of Formula I crude (purity of 82.5%) and 3.5 mL of IPA. The mixture was heated to 45 C. under stirring until the entire solid dissolved. At 45 C., 6 mL of water was added drop-wise. The mixture was stirred for 10 min and cooled slowly to 010 C. The mixture was stirred at 010 C. for 10 min and filtered to obtain the recrystallized compound of Formula I having a purity of 98%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 152628-03-0

A suspension of 2 (2.18 g, 10 mmol) in thionyl chloride (20 mL, 276 mmol) was refluxed for 2 h, and then the excess thionyl chloride was removed under a vacuum to provide the crude acid chloride (3) as an off-white solid. The crude product 3 was used in the next step without further purification.

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 152628-03-0.

Reference:
Article; Zhang, Jun; Wang, Jin-Liang; Zhou, Zhi-Ming; Li, Zhi-Huai; Xue, Wei-Zhe; Xu, Di; Hao, Li-Ping; Han, Xiao-Feng; Fei, Fan; Liu, Ting; Liang, Ai-Hua; Bioorganic and Medicinal Chemistry; vol. 20; 14; (2012); p. 4208 – 4216;,
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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Example 1[51] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzamide [52][53] Method A[54] In a reactor, potassium tert-butoxide (20.9g, 186.56mmol) was dissolved in tetrahydrofuran (167ml), and then was cooled to -20+50C. To the resultant product, 3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) dissolved in tetrahydrofuran (80ml) was added and stirred for 30 minutes. When the stirring was completed, 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester (15.5g, 45.60mmol) dissolved in tetrahydrofuran (90ml) was slowly added to the resultant product. After the addition, the temperature of the mixture was slowly elevated to room temperature, and stirring was carried out until the reaction was completed. When the reaction was completed, the reaction mixture was cooled to 5-1O0C, and then 15% sodium chloride aqueous solution (337ml) was slowly added to the reaction mixture. After the addition, the temperature of the reaction mixture was slowly elevated to room temperature again, and then water (170ml) was added thereto and an organic layer was extracted and separated.[55] To the organic layer, ethyl acetate (400ml) was added. Then, the layer was washed with water (200ml), separated and was subjected to vacuum concentration. When the concentration was completed, methanol (220ml) was added thereto. Then, the resultant layer was subjected to reflux- stirring for 1 hour, cooled to room temperature, and then stirred for 2 hours.[56] The obtained solid was filtered, sufficiently washed with methanol (100ml), and then dried to provide a pale yellow solid final compound (17.51g, yield 81%).[57] 1H-NMR(DMSOd6, delta= 2.19(s,3H), 2.36(s,3H), 7.24(s,lH), 7.35(m,2H), 7.47 (s,lH),7.64(d,lH), 7.71(d,lH), 7.92(d,lH), 8.01(s,lH), 8.11(s,lH), 8.30(s,2H), 8.47(d,lH), 9.00(s, IH), 10.49(s,lH)

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem