Author: Jessica.F

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

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

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

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

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.

The compound 5-e (540 mg, 1.30 mmol), compound 29-e (see Patent: WO2012142237)(400 mg, 1.37 mmol), potassium carbonate (360 mg, 2.60 mmol) and ethanol (20 mL) was refluxed for 1 hour. Will reverseThe mixture was concentrated under reduced pressure, dichloromethane (50 mL) was added, washed successively with water (20 mL x 3) and saturated brine (50 mL).The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from petroleum ether and ethyl acetate to giveCompound 29-d (590 mg, 78%) as a white solid.

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:
Patent; Shanghai Yingli Pharmaceutical Co., Ltd.; Xu Zusheng; Lou Yangtong; Wu Tianzhi; (87 pag.)CN106478634; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 822-36-6, name is 4-Methyl-1H-imidazole, 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 822-36-6, Recommanded Product: 822-36-6

Example 18: Preparation of 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl benzoic acid : In 3 lit four necked round bottom flask equipped with mechanical stirrer, thermometer, reflux condenser and an addition funnel, 3-fluoro-5-(trifluoromethyl)benzoic acid (80 g), 4-methylimidazole (47.2 g) and dimethylacetamide (400 ml) was added, heated to 80-85C and stirred for 12 hrs at the same temperature. The reaction mass was cooled to room temperature, diluted with water (500 ml) and extracted with ethyl acetate (1000 ml). The solvent from organic layer was distilled off under vacuum and th obtained residue was titrated with water to get the title compound. Yield: 63 g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; LAURUS LABS LTD; BOLLU, Ravindra Babu; BANDLAMUDI, Veera Narayana; KUDIRILLA, Vivek Kumar; VEMULA, Rambabu; VASIREDDI, Uma Maheswer Rao; (36 pag.)WO2019/130254; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 152628-02-9, 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. 152628-02-9 name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 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.

90 gm of BIM in 500 ml DMF was added at about 150C followed by addition of 41.4 gm potassium tertiary butoxide and stirred for about 15-20 minutes at 15-200C. 138.7 gm of Ethyl-4-(bromomethyl) biphenyl-2-carboxylate in 250 ml DMF was added slowly over 45 to 60 minutes maintaining temperature 15-200C. The reaction mixture was stirred for about 30 minutes. 1500 ml of Ethyl acetate and 2000 ml water were added to the reaction mixture at 20-300C and the layer was allowed to separate. Aqueous layer was extracted with 1000 ml of ethyl acetate. The combined organic layer was washed with water [3 X 1000 ml]. The organic layer was dried over anhydrous sodium sulfate and dried ethyl acetate solution was filtered. The ethyl acetate was removed by distillation under vacuum at 50-550C. 500 ml of fresh ethyl acetate was added to the residue to make a solution at 60-650C. The reaction mixture was cooled to 50-550C. 200 ml of hexane was added and stirred for 30 minutes. The reaction mixture was cooled to 100C and further stirred for about 1 hour at 5-10 C.The material was filtered and washed with a mixture of ethyl acetate and 200 ml hexane (7:3 v/vl) at 8-120C. The wet cake was dissolved in 600 ml ethyl acetate at 60-650C and cooled to ~50 0C. 240 ml of hexane was added and mixture was cooled with stirring to 100C and then stirred for about one hour. The material was filtered and washed with a mixture of 120 ml Ethyl acetate and hexane (7:3 v/v) at 8-12 C. The material was suction dried and used as such. 108.2 gm of product is obtained with 99.6 % purity (By HPLC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; CADILA PHARMACEUTICALS LTD.; KHAMAR, Bakulesh, Mafatlal; SIDDIQUI, Ishrat, Husain; PONNAIAH, Ravi; MODI, Indravadan, Ambalal; WO2010/18441; (2010); A2;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H4N2

(1) will p-nitrochlorobenzene 0.158g (1.0mmol), imidazole 0.069g (1.0mmol), Cu (OAc)2·H2O 0.030g (0.15mmol), 2,2- biimidazole 0.022g (0.15mmol), cesium carbonate 0.652g (2mmol), DMSO (2mL) was added the reaction tube with a piston, was heated to 80 deg.] C with stirring for 48 hours reaction.(2) TLC until the reaction was complete the reaction was followed ends.After the reaction was cooled to room temperature, diluted with water, extracted with ethyl acetate 3-4 was added, and the combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product.After the end of (3) to obtain the crude product was purified by column chromatography (petroleum ether / ethyl acetate elution) to give the desired product 17 (79% yield).

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; Soochow University (Suzhou); Zeng Runsheng; Zhou Chunmei; Zou Jianping; (15 pag.)CN104447557; (2017); B;,
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. 25676-75-9, name is 4-Bromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Product Details of 25676-75-9

General procedure for preparation of Compound 10-6: A solution of Compound 10-3 (169 mg, 0.3 mmol) in a mixture of dioane (10 mL)-H20 (1 mL), was added Compound 10-5 (55.8 mg, 0.3 mmol), Cs2C03 (195 mg, 0.6 mmol) and Pd(dppf)Cl2 (22 mg, 0.03 mmol) and heated under irradiation of M W at 130C for 30 min under N2. Catalyst was filtered through diatomite and concentrated in vacuum to give the crude product (100 mg, yield 61.3%).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC; CHEN, Huifen; CRAWFORD, Terry; MAGNUSON, Steven, R.; NDUBAKU, Chudi; WANG, Lan; WO2013/113669; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, 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. category: imidazoles-derivatives

EXAMPLE 23 1-(6-{[(1S)-1-(3-Fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6 carboxamide: To a stirred mixture of 6-chloro-N-[(1S)-1-(3-fluorophenyl)ethyl]pyrazin-2-amine (242 mg, 0. 96 mmol) and 5-benzimidazole carboxamide (318 mg, 1. 97 mmol, 2, 1 eq) in 18 dimethylformamide (5 mL) was added cesium carbonate (460 mg, 1.41 mmol, 1.5 eq). This solution was then heated at 120C under a nitrogen atmosphere for 48 hours at which time a second amount of cesium carbonate (180 mg, 0. 6 eq) was added. The mixture was heated at 120C for a further 62 hours before being cooled to room temperature, diluted with chloroform (15 mL) and filtered, The filtrate was then concentrated in vacuo and subjected to silica column chromatography (stepwise gradient from dichloromethane to 9: 1 dichloromethane : methanol) to yield the 5-carboxamide product (100. 7 tng, 28%) along with the desired 6-carboxamide product (63.7 mg, 18%). ‘H NMR (d6-acetone, 300 MHz) No. 1.64 (3H, d, J = 6. 9 Hz), 2.76-2. 80 (2H, brm), 5.35 (1H, m), 6.93 Cm, m), 7. 29-7. 36 (3H, m), 7. 42 (1H, dm,/= 7. 7 I Iz), 7. 77 (1H, dd, J = 8.5, 0.5 Hz), 7.93 (1H, dd, 1. 7, 8. 5 Hz), 8.05 (1H, s), 8. 31 (1H, s), 8. 73 (1H, s), 8.40 (1H, dd, J = 0. 5, 1. 6 Hz). MS (c. i.) m/z 376 (M+, 89%).

The synthetic route of 1H-Benzo[d]imidazole-6-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem