Category: imidazoles-derivatives

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(1H-Benzo[d]imidazol-2-yl)aniline

Example 37: Preparation OF 2-BENZO L, 3] DIOXOL-5-VL-N- [3- (LH-BENZIMIDAZOL-2-YL)- PHENYLL-ACETAMIDE (Compound M To a 5.0 ml methylene chloride solution of (3,4-methylene-dioxy) phenyl acetic acid (182. 9 mg, 1.0 mmol) was added methylene chloride oxalyl chloride solution (2 M, 0.60 ml, 1.2 mmol). Five drops of DMF was added with stirring at ambient temperature. Methylene chloride and other volatile materials were removed by reduced pressure after it was stirred at ambient temperature for 3.0 h. To the residue was added DMAP (10 MG), 4-(1H-benzimidazol-2-yl)-phenylamine (83 mg, 0.40 mmol) and pyridine (2.0 ml). The mixture was stirred at 60 C for 20 hrs. Water (20 ml) was added. The solid formed was collected and was washed with aq. NAOH (3 N, 2x 10 ml), water (10 ml), aq. HCl (2 N, 3 x 10 ml), water (2 x 5 ml), ether (2 x 5 ml). An off-white compound (12 mg, 8%) was obtained. MS M/Z = 372.05 (M+H) ; IH NMR delta 10.56 (s, 1 H), 8.15 (d, J=8. 7 Hz, 2 H), 7. 87 (d, J=8. 7 Hz, 2 H), 7.72 (m, 3 H), 7.42 (m, 2 H), 6.94-6. 80 (m, 3 H), 6.00 (s, 2 H), 3.63 (s, 2H).

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/30206; (2005); 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. 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. Recommanded Product: 2-(Hydroxymethyl)-5-bromobenzimidazole

Synthesis of 5-bromo-1H-benzimidazole-2-carboxylic acid hydrochloride 44 was prepared using 5-bromo-1H-benzimidazole-2-yl)-methanol 28 (0.23 g, 1.0 mmol) dissolved in acetone (10 mL) and potassium permanganate (0379, 2.4 mmol) dissolve in water (10 mL). The crude product was recrystallised from water. 5-Bromo-1H-benzimidazole-2-carboxylic acid in Yield 37% was recovered as a creamy white powder.

The synthetic route of 540516-28-7 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

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (purity 55%)(516 mg, 12.0 mmol) was added to a N,N-dimethylformamide solution (8.0 ml) of 2-chloro-1H-benzimidazole (1.52 g, 10.0 mmol), at 0C, under nitrogen stream, and stirring was carried out for 20 minutes. Methyl iodide (0.750 ml, 12.0 mmol) was further added, and stirring was carried out under room temperature for 2 hours. Water was added to the reaction solution, and the resulting solid substance was collected by filtration to afford 2-chloro-1-methyl-1H-benzimidazole (1.51 g, yield 91%) as a white solid.

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

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2466-76-4, 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. 2466-76-4 name is 1-(1H-Imidazol-1-yl)ethanone, 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.

Step 7: Synthesis of methyl 2-(2-bromophenyl)-3-oxobutanoate: To a stirred solution of methyl 2-(2-bromophenyl)acetate ( 2 g, 8.72 mmol) in dry THF ( 20 mL) at -78 °C, LiHMDS (1M in toluene, 17.4 mL, 17.4 mmol) was added under nitrogen atmosphere and stirring was continued for 1 h. Then a solution of l-(lH-imidazol-l- yl)ethanone (1.15 g, 10.47 mmol) in dry THF:DMF (10 mL: 2mL) mixture was added. The reaction mixture was allowed to warm up to ambient temperature. The progress of the reaction was monitored by TLC. Upon completion the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the title compound (2.1 g, 88percent).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10078; (2015); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 53316-51-1, name is 4,5-Dimethyl-1H-imidazole hydrochloride, 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 53316-51-1, category: imidazoles-derivatives

Step 1 : l-(2-((tert-butyldimethylsiIyl)oxy)ethyl)-4,5-dimethyl-lH-imidazole [001009] A solution of 4,5-dimethyl- lH-imidazole hydrochloride (2.94 g, 22.2 mmol) was in N,N-dimethylformamide (30.0 mL, 387 mmol) was cooled to 0 C. Sodium hydride (3.55 g, 88.7 mmol) was slowly added and the solution was stirred for 30 mins at 0 C. Potassium iodide (4.417 g, 26.61 mmol) and (2-bromoethoxy)-tert-butyldimethylsilane (6.365 g, 26.61 mmol) were added and the mixture was allowed to warm to room temperature with stirring over 30 minutes. The reaction as quenched with methanol (3 mL) and diluted with water ( 150 ml). The resulting aqueous mixture was extracted with ethyl acetate (3 x 70 mL). The combined organic portions was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 15% MeOH in EtOAc) to provide 4.34g (77%) of the title compound. NMR (400 MHz, Chloroform-Patent; DUFFEY, Matthew O.; ENGLAND, Dylan; FREEZE, Scott; HU, Zhigen; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; ONO, Koji; XU, He; (684 pag.)WO2016/4136; (2016); 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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Chloro-6-(trifluoromethyl)benzimidazole

Preparation 16 tert-Butyl 2-chloro-5-(trifluoromethyl)-1H-1,3-benzimidazole-1-carboxylate STR61 Di-tert-butyldicarbonate (593 mg) was added to a solution of 2-chloro-5-(trifluoromethyl)-1H-1,3-benzimidazole (500 mg) [see JP 02306916 A2 901220] in acetonitrile (5 ml), and dimethylaminopyridine (27 mg) was then added. The reaction mixture was stirred for 10 minutes at room temperature, after which time the solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluding with a solvent gradient of 100:0 changing to 85:15, by volume, hexane:ethyl acetate, in 5% increments, to afford tert-butyl 2-chloro-5-(trifluoromethyl)-1H-1,3-benzimidazole-1-carboxylate (678 mg) as a gum, as 1:1 mixture of regioisomers. 1 H-NMR (CDCl3)delta: 8.25 (0.5H, s), 8.05 (0.5H, d), 7.95 (0.5H, s), 7.80 (0.5H, d), 7.60 (1H, d), 1.80 (9H, s).

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 123470-47-3,Some common heterocyclic compound, 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H4F2N2S, 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.

Under argon atmosphere, N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]-2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]acetamide (4.0 g, 8.43 mmol), 5,6-difluoro-2-mercaptobenzimidazole (5.8 g, 31.2 mmol) and triphenylphosphine (7.8 g, 29,7 mmol) were dissolved in N,N-dimethylformamide (170 mL), and under cooling with ice diethyl azodicarbonate (40% w/v toluene solution, 11.0 mL, 25.3 mmol) was added dropwise to the mixture, followed by stirring for 1.5 hours at the same temperature. To the reaction mixture, ethylacetate and 1 mol/L of hydrochloric acid, and aqueous layer was separated. The organic layer was further extracted with 1 mol/L hydrochloric acid. The aqueous layer was combined and the resultant mixture was alkalized by sodium hydroxide (1 mol/L), followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (developing solvent; chloroform ammonia-saturated methanol=100:3), to thereby yield 2-[4-[2-(5,6-difluorobenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (4.9 g, yield: 90.1%) as colorless crystals.

The synthetic route of 123470-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kowa Co., Ltd.; US2005/20606; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, A common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, molecular formula is C4H5BrN2, 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.

Intrmdiate Example 11.5-(I-Methyl-1H-imidazol-4-yl)-1H-benzo[d]imidazolea) 4-(1-Methyl-1H-imidazol-4-yl)-2-nitroanilineA solution, of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(1.45 g, 5.55 mmol, 1.1 eq) in 1 ,2-dimethoxyethane (15 ml) was degassed by N2bubbling for 5 mi 4-Bromo-1-methyi-1H-imidazole (0.81 g, 5 mmol, 1 eq) was added and the mixture was degassed for another 5 mm. Pd(dppf)Cl2 (0.4 g, 0.5 mmol, 0.1 eq) and aqueous sodiumcarbonate (1.59 g, 15 mmol, 3 eq) were added, sequentially using the procedure of Intermediate Example 1 and then heated at 100 C for 4 h. The reactionmixture was then quenched and extracted as in Intermediate Example 1. The solvent was distilled off to afford the crude residue which was purified by columnchromatography (60-120 silica gel, 50 % ethyl acetate in hexane) to afford the title product in 60 % yield (0.6 g). LC-MS (ESI): Calculated mass: 218.08; Observed mass:219.2 [M+HJ (rt: 0.09 mm).

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; RAJAGOPALAN, Srinivasan; APPUKUTTAN, Prasad; NARASINGAPURAM ARUMUGAM, Karthikeyan; UJJINAMATADA, Ravi Kotrabasaiah; GEORGE, Shyla; LINNANEN, Tero; WO2014/162039; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 36947-68-9,Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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.

Preparation 20; 4-(2-isoPropyl-1H-imidazol-1-yl)piperidine; Methanesulphonyl chloride (0.27 mL, 3.4 mmol) was added dropwise to a stirring mixture of 1-tertbutoxycarbonyl-4-hydroxypiperidine (457 mg, 2.27 mmol) and triethylamine (0.95mL, 6.8 mmol) in dichloromethane (10 mL) at 0 C. under nitrogen. After 20 mins, the mixture was allowed to warm to room temperature and stirred for a further 30 mins. Water (10 mL) was added and the organic layer was separated and the solvent evaporated under reduced pressure. The residue was taken up in acetonitrile (10 mL) and 2-isopropylimidazole (250 mg, 2.27 mmol) and cesium carbonate (880 mg, 22.7 mmol) were added. The mixture was refluxed for 3 days and then allowed to cool. The mixture was filtered and the solvent was removed in vacuo. The residue was filtered through a silica plug using ethyl acetate and the solvent was removed under reduced pressure. The residue was dissolved in methanol (5 mL) and ethereal hydrogen chloride (5 mL of a 2N solution) was added. The mixture was stirred overnight, the solvent was removed in vacuo and the residue was chromatographed on silica gel using an elution gradient of dichloromethane to 94:6:0.6 dichloromethane:methanol:0.88 ammonia as eluant to afford the title compound as a white solid, 28 mg.LRMS: m/z APCI 194 [MH]+

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

Reference:
Patent; PFIZER INC; US2009/209578; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16681-56-4, 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. 16681-56-4, name is 2-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To 7.3 g (50 mmol) of 2-bromo-1H-imidazole, 11.1 g of 9-anthracene boronic acid(50 mmol) and 3.5 g (5 mmol) of bistriphenylphosphine palladium dichloride were added 130 ml of 2M aqueous sodium carbonate solution, 260 ml of methylBenzene and 86 ml of ethanol at 100 C for 12 hours. After the system had cooled down, extract with methylene chloride and wash with distilled waterThe organic phase is then washed with anhydrous magnesium sulfate and the solvent is evaporated to dryness. Column chromatography (n-hexane: dichloromethane = 20: 1)Purification gave 8.43 g of intermediate A-1.

The synthetic route of 2-Bromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhou Wenting; Cai Hui; (17 pag.)CN107383071; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem