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. 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O

To a solution of 1,3-dihydro-1,N-methyl-2-oxobenzimidazole (3.185 g, 21.5 mmol) in DMF (60 mL) is added NaH (60% in mineral oil,1.03 g, 25.78 mmol) portionwise at 0 C. After stirring at 0 C for 30 min.2,4-dichloropyrimidine (3.20 g, 21.5 mmol) is added, and the mixture is allowed to stir at 15 C for 12 hrs. The resulting mixture is quenched with water (200 mL) and the mixture is extracted with EtOAc (100 mL x 3), and washed with water (100 mL x 4), dried with Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (petroleum ether: EtOAc =10:1), to give 2-chloro-4-(1,3-dihydro-3,N-methyl-2-oxobenzimimidazol-1-yl)pyrimidine.

According to the analysis of related databases, 1849-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CS PHARMASCIENCES, INC.; SONG, Yuntao; BRDIGES, Alexander, James; (524 pag.)WO2017/120429; (2017); 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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Preparation of 4-[(2′-dimethylaminomethyl)imidazol-1′-yl]aniline. To a solution of 4-fluoronitrobenzene (7.87 g) and 2-imidazole-carboxaldehyde (5.90 g) in DMF (60 mL) was added K2CO3 (9.26 g). The mixture was heated at 80C under N2 for 16 h. The mixture was poured into water, and the precipitate was filtered to give 6.70 g of yellow solid. The filtrate was then extracted with EtOAc, and the organic layer was washed brine, dried over MgSO4, and concentrated to a yellow solid (5.40 g). Both batch were identified as the 4-[(2′-carboxaldehyde)imidazol-1′-yl]nitrobenzene. ESI mass spectrum z (rel. intensity) 218 (M+H, 100).

The synthetic route of 10111-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP991638; (2005); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 muM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H2O (1.0 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into an oil bath, which was preheated to 70 C (90 C for alkyl amine, 120 C for imidazole). The reaction mixture was stirred for another 16 h (8 h for imidazole). After allowing the mixture to cool to room temperature, the reaction mixture was filtrated, the precipitates were washed with water and ethyl acetate thoroughly. The filtrate was extracted with ethyl acetate (3¡Á25 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel to afford the desired products.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Liye; Yu, Ruina; Zhu, Xinhai; Wan, Yiqian; Tetrahedron; vol. 69; 42; (2013); p. 8974 – 8977;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4887-83-6, 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. 4887-83-6 name is 7-Methyl-1H-benzo[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.

To a solution of 1 -chloro-5-fluoro-3,3,4,4-tetramethyl-isoquinoline (1 .67 mmol, 0.430 g) in pyridine (0.20 M, 9.0 mL) at room temperature was added 4-methyl-1 H-benzimidazole (1 .5 equiv., 2.69 mmol, 0.356 g) and the mixture was stirred at 90 C for 15 hours. The reaction mixture was allowed to cool down to room temperature and then concentrated under vacuo. The residue obtained was purified by flash chromatography to give 5-fluoro-3,3,4,4- tetramethyl-1 -(4-methylbenzimidazol-1 -yl)isoquinoline (0.525 g, 87% yield) as a beige solid : mp= 1 18-120C, LC-MS (Method G) UV Detection: 220 nm, Rt = 1 .19, MS: (M+1 ) = 336; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1 .32 (s, 6 H) 1 .47 (s, 6 H) 2.71 (s, 3H) 6.91 -6.95 (m, 1 H) 7.10 – 7.25 (m, 5 H) 8.18 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Methyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; BOU HAMDAN, Farhan; QUARANTA, Laura; TRAH, Stephan; WEISS, Matthias; (101 pag.)WO2016/156085; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 3034-38-6, name is 5-Nitro-1H-imidazole, molecular formula is C3H3N3O2, 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. Product Details of 3034-38-6

Nitroimidazole (4.52 g, 40 mmol) was dissolved in conc. aq NH3 (70 mL) to give a clear yellow solution. A solution of silver nitrate (6.8 g, 40 mmol) in water (40 mL) was added dropwise(20 min) with moderate stirring at rt. After further stirring (10 min) the resultant pale yellow precipitate was filtered off, washed well with ethanol and dried under high vacuum to give the product 11 (8.16 g, 93%) as apale yellow/white chalky powder. mp >300 C (lit.17, > 300 C). 1H NMR (250.1 MHz, DMSO-d6): d 7.34 (s, 1H,CH), 7.89 (s, 1H, CH), not observed (CNO2). MS (CI) m/z (%) 112 (M-, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3034-38-6, its application will become more common.

Reference:
Article; Clayton, Russell; Davis, Michael L.; Li, Wei; Fraser, William; Ramsden, Christopher A.; Arkivoc; vol. 2017; 3; (2017); p. 87 – 104;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

A small sample of the free base (50mg) was derivatized as its trifluoroacetyl analogue for chiral HPLC analysis. The sample was dissolved in acetonitrile (4ml) and treated with 1- (trifluoroacetyl)imidazole (0.4ml). The solution was stirred at 65 for 1 h, concentrated in vacuo and the residue dissolved in dichloromethane (5ml). The organic layer was washed with dilute sulphuric acid(2ml), then the organic layer concentrated and disssolved in hexane-isoproplyalcohol (98:2) for injection onto the HPLC column. Chiral HPLC (Chiracel-OD-H column, lot no. 09-02-20709, eluent hexane-isopropylalcohol 98:2, flow rate 1 ml/min, detection uv 230nm, temperature 40) retention time 12.93 mins.

The chemical industry reduces the impact on the environment during synthesis 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-50-2, These common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, 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: preparation of tert-butyl 4-formyl-1 H-imidazole-1-carboxylateTo di-tert-butyl dicarbonate (23.25 g, 107 mmol) and 1H-imidazole-4-carbaldehyde (9.75 g,101 mmol) in THF (200mL) was added DMAP (100 mg, 0.819 mmol). The reaction was stirredfor two hours. The reaction mixture was then diluted with saturated NaHCO3 solutuion/EtOAc(100 mL/100 mL). The aqueous was then extracted with EtOAc (2 x 100 mL) and thecombined organic was dried (Na2504) and concentrated to give crude product (19.9 g). m/z197.2 (M + H)

Statistics shows that Imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 3034-50-2.

Reference:
Patent; NOVARTIS AG; CHO, Young Shin; LEVELL, Julian Roy; LIU, Gang; SHULTZ, Michael David; VAN DER PLAS, Simon Cornelis; WO2014/141153; (2014); 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. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(1-Trityl-4-imidazolyl)benzaldehyde

2-(1-triphenylmethyl-1H-imidazol-4-yl)benzaldehyde (0105-1) (263 mg, 0.635 mmol, 1 eq),Compound (2-(6-Fluoro-2,3-dihydrobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0403-42) (377 mg, 1.3 mmol, 1.3 eq. )And cesium carbonate (412 mg, 1.27 mmol, 2 eq.)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product 1-(6-fluoro-2,3-dihydrobenzofuran-5-yl)-3-(2-(1-triphenylmethyl-1H-) Imidazol-5-yl)phenyl)prop-2-en-1-one (280 mg, crude) was a yellow solid.

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 103057-10-9, 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 103057-10-9 as follows.

4.1. 1,1-dimethylethyl (S)-2-[[(phenylmethoxy)carbonyl]amino]-4-[[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]thio]butanoate 6 g of potassium thioacetate is added to a solution of 3.58 g (10 mmoles) of 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole in 40 ml of ethanol under nitrogen. The reaction mixture is agitated by sonification for 15 minutes before being poured onto ether. The organic phase is washed successively with water, a saturated solution of sodium hydrogen carbonate, a saturated solution of sodium chloride, before being dried over magnesium sulphate and evaporated under reduced pressure. The residue is dissolved in 100 ml of methanol degassed with nitrogen and containing 1.9 ml (10 mmoles) of a 5.3N solution of sodium methoxide. After stirring for 15 minutes, a solution of 4.63 g (10 mmoles) of 1,1-dimethylethyl (S)-4[[4-methylphenyl)sulphonyl]-2[[(phenylmethoxy)carbonyl]amino]butanecarboxylate in 40 ml of degassed methanol is added. The reaction mixture is stirred for 24 hours at room temperature and the precipitate obtained is drained and washed with methanol and then with water. 3 g of product is obtained after drying. Melting point=183-185 C. Yield=50%

According to the analysis of related databases, 103057-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Synthelabo; US5453430; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, A common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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.

To 38.1 g (0.250 mol) 2-chlorobenzimidazole, 25.6 g 0.275 mol) aniline in 250 ml NMP 26.4 g(0.275 mmol) methane sulfuric acid is added. The reaction mixture is stirred at 100 00 for 3 hunder nitrogen. The reaction mixture is poured on a saturated solution of sodium hydrogencarbonate in water. The water phase is extracted with ethyl acetate. The organic phase is 3times washed with water and the organic phase is dried with magnesium sulfate. The solvent is removed in vacuum. The product is decocted in 100 ml dichloromethane.Yield 43.6 g (83%)The above reaction is carried out according to a procedure given in US20090186879 (page 57).1H NMR (400 MHz, DMSO-d6): oe = 10.9(s, 1H), 9.38 (s, 1H), 7.29-7.36(d, 2H), 2.29-7.36(m,4H), 6.96-7.02(m, 2H), 6.91-6.94 (m, 1H).

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; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; BARDON, Kristina; NAGASHIMA, Hideaki; (315 pag.)WO2017/56055; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem