Category: imidazoles-derivatives

Synthetic Route of 33468-67-6, These common heterocyclic compound, 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-1H-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.

a) To a vial was added 2-methyl-4-(trifluoromethyl)-1H-imidazole (750 mg, 5 mmol), 5 mL of THF, 2.5 mL of DMF, and K2CO3 (2.07 g, 15 mmol). To this mixture was slowly added ethyl bromoacetate (1.00 g, 6 mmol). After 2 hours, the slurry was diluted with EtOAc, filtered on Celite, and concentrated. The residue was purified by flash chromatography (SiO2, 80 g column, eluting with 15-100% EtOAc in hexanes) to provide 476 mg (40%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.20 (s, 1H), 4.61 (s, 2H), 4.28 (q, J=7.0 Hz, 2H), 1.63 (s, 3H), 1.31 (t, J=7.0 Hz, 3H); MS: (ES) m/z calculated for C9H12F3N2O2 [M+H]+ 237.1, found 237.1. The regiochemistry of the system was confirmed by nOe between the alpha-methylene and both the imidazole ring and methyl protons.

The synthetic route of 33468-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15813-09-9, 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. 15813-09-9, name is 4,5-Diiodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

4,5- Diiodoimadazole (15.1 g, 47 mmol) and 2-aceteoxyethyl acetoxymethyl ether (Compound 4, 10.0 g, 57 mmol) were dissolved in anhydrous acetonitrile (150 mL) under inert atmosphere. N,0-bis(trimethylsilyl) acetamide (70.0 mL, 284 mmol) was added. The reaction mixture was stirred at rt for 5 h, and then cooled to 0C. Trimethylsilyl triflouromethane sulfonate (14.0 mL, 71 mmol) was added slowly and then the solution was heated to 90C and stirred for 12 h. The reaction mixture was quenched by addition of aq. NaHC03 (30 mL) and stirred for 30 min. The solution was separated and the aqueous layer was extracted with CH2C12 (2 x 50 mL). The organic layers were combined, washed with H20 (3 x 50 mL) and brine (50 mL), and dried over MgS04. The solvent was removed under reduced pressure. The resultant syrup was purified by flash chromatography over silica gel to obtain colorless solid compound 5. (11.6 g, 47%). 1H NMR (CDC13, 400 MHz): delta 7.73 (1H, s), 5.35 (2H, s), 4.19 (2H, t, J= 4.6 Hz), 3.64 (2H, t, J= 4.6 Hz), 2.06 (3H, s). 13C NMR (CDC13, 100MHz): delta 170.9, 141.8, 97.5, 81.9, 78.1, 66.9, 62.8, 21.0. HRMS calcd for C8Hi0I2N2O3 436.8859, found 436.8860 [M + H+].

The chemical industry reduces the impact on the environment during synthesis 4,5-Diiodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE COUNTY; KATHOLIEK UNIVERSITEIT LEUVEN; LIEDEN UNIVERSITY MEDICAL CENTER; RADTKE, Katherine, L.; PETERS, Hannah, L.; NEYTS, Johan; JOCHMANS, Dirk; SNIJDER, Eric, J.; (33 pag.)WO2016/123318; (2016); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 75370-65-9,Some common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H7N3O, 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 a solution of 29f (0.48g, 1.85 mmol) in THF (20mL) was added CDI (2.1 mol eq, 0.63g) and the mixture was heated for 5 h. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure. The oil obtained (0.78 g, quantitative yield) was dissolved in DMF (20 mL) and the bicyclic amine la was added (0.8 mol eq, 0.26g), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (9.5:0.5 EtoAc:MeOH) to obtain the product as a pale yellow solid (0.14g, 0.32 mmol, 15% Yield). 1HNM (DMSO, 400 MHz) delta 1.63 (m, 6H), 3.09 (m, 4H), 4.36 (d, 2H, J=6), 6.61 (d, 1H, J=8), 6.84 (t, 2H), 6.95 (d, 1H, J=6), 7.42 (d, 1H, J=8), 7.87 (d, 1H, J=6), 8.37 (s, 1H), 10.01 (bs, 1H), 10.59 (bs, 1H). [M+1] 434.91 (C20H21F3N6O2 requires 434.41).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); 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. 131020-36-5, name is Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate

Example 11B : 5-Hydroxymethyl-l-methylbenzimidazole A solution of methyl [L-METHYLBENZIMIDAZOLE-5-CARBOXYLATE] (1.6 g, 8.42 mmol) in dry THF (80 mL) was treated with [LIALH4] (1.59 g, 42.1 mmol) and the mixture stirred for 2 hours. 1.5 mL of 5% [NAOH] solution was then added, and the solid which precipitated was filtered through diatomaceous earth. The filtrate was collected and the solvent removed under reduced pressure to give 0. [8] g of the title compound. [C9HLON20] NMR (400 MHz, DMSO-d6): 3.85 (3H, s, NCH3) ; 4.65 (2H, s, [CH20H)] ; 5.25 [(1H,] bs, OH); 7.3 [(1H,] dd, [J =] 1 and [8] Hz, aryl-H); 7.55 [(1H,] d, [J] [=] [8] Hz, aryl-H); 7.65 [(1H,] d, J= 1 Hz, aryl-H); 8.2 [(1H,] s, imidazole-H)

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; AMGEN, INC.; WO2003/99814; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2620-76-0, 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. 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 50 mL three-neck flask were put 1.4 g (5.2 mmol) of 2-(4-bromophenyl)-1,3-benzoxazole, 0.8 g (2.5 mmol) of N,N’-diphenylbenzidine, 1.0 g (10 mmol) of sodium tert-butoxide, and 28 mg (50 mumol) of bis(dibenzylideneacetone)palladium(0), and the air in the flask was replaced with nitrogen. Then, 20 mL of dehydrated xylene was added to this mixture. After the mixture was deaerated while being stirred under reduced pressure, 0.3 mL (0.2 mmol) of tri(tert-butyl)phosphine (10 wt percent hexane solution) was added thereto. This mixture was stirred under a nitrogen atmosphere at 130° C. for 4.5 hours to be reacted.After the reaction, 200 mL of ethyl acetate was added to this reaction mixture, and this suspension was filtered through Florisil and Celite. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent, toluene:ethyl acetate=9:1). The obtained fraction was concentrated, and acetone and methanol were added thereto. The mixture was irradiated with supersonic and then recrystallized, so that the object of the synthesis was obtained as 1.7 g of a yellow powder in a yield of 96percent.A reaction scheme of the above synthesis method is illustrated in the following scheme (B-1). The Rf values of the object of the synthesis, 2-(4-bromophenyl)-1,3-benzoxazole, and N,N’-diphenylbenzidine were respectively 0.35, 0.67, and 0.30 which were found by silica gel thin layer chromatography (TLC) (developing solvent, ethyl acetate_hexane=1:5).Results of nuclear magnetic resonance spectrometry (1H-NMR), by which the compound obtained by the above synthesis method was analyzed, are shown below. In addition, the 1H-NMR charts are shown in FIGS. 10A and 10B. FIG. 10B illustrates an enlarged view within a range of 6 ppm to 9 ppm in FIG. 10A. The results reveal that N,N’-diphenyl-N,N’-di-{4-(1,3-benzoxazol-2-yl)-phenyl}benzidine (abbreviation: BOxABP), which is the triarylamine compound of one embodiment of the present invention represented by the structural formula (135) shown above, was obtained.1H NMR (CDCl3, 300 MHz): delta (ppm)=7.11-7.24 (m, 14H), 7.28-7.35 (m, 8H), 7.51-7.55 (m, 6H), 7.70-7.73 (m, 2H), 8.90 (d, J=8.7 Hz, 4H).Next, ultraviolet-visible absorption spectra (hereinafter, simply referred to as “absorption spectra”) and emission spectra of BOxABP were measured. The absorption spectra were measured using an ultraviolet-visible light spectrophotometer (V550 type manufactured by Japan Spectroscopy Corporation). The emission spectra were measured using a fluorescence spectrophotometer (FS920 manufactured by Hamamatsu Photonics Corporation). The absorption spectra and the emission spectra of a toluene solution of BOxABP and a thin film of BOxABP were measured. Put in a quartz cell, the toluene solution (0.120 mmol/L) was subjected to the measurements at room temperature. As for the measurements of the absorption spectrum of the thin film, the thin film which was evaporated over a quartz substrate was used and a value obtained by subtraction of an absorption spectrum of quartz from absorption spectra of the thin film and quartz is shown.FIGS. 11A and 11B show measurement results of the absorption spectra and emission spectra. FIG. 11A shows the measurement results of the toluene solution of BOxABP. FIG. 11B shows the measurement results of the thin film of BOxABP. In each of FIGS. 11A and 11B, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit) or emission intensity (arbitrary unit). In each of FIGS. 11A and 11B, the two solid lines are shown, and the thin line represents absorption spectrum while the thick line represents emission spectrum.In the case of the toluene solution of BOxABP, an absorption peak is observed at around 381 nm as shown in FIG. 11A. In the case of the thin film of BOxABP, an absorption peak is observed at around 384 nm as shown in FIG. 11B.Further, in the case of the toluene solution of BOxABP, the maximum emission wavelength is 435 nm (excitation wavelength: 380 nm) as shown in FIG. 11A. In the case of the thin film of BOxABP, the maximum emission wavelength is 472 nm (excitation wavelength: 400 nm) as shown in FIG. 11B.As described above, BOxABP was found to emit blue light and accordingly can be used for a blue light-emitting material.Further, the HOMO level and the LUMO level of BOxABP were obtained by cyclic voltammetry (CV) measurements. An electrochemical analyzer (ALS model 600A or 600C, manufactured by BAS Inc.) was used for the CV measurements.Further, as for a solution used for the CV measurements, dehydrated dimethylformamide (DMF, manufactured by Sigma-Aldrich Inc., 99.8percent, Catalog No. 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (n-Bu4NClO4, manufactured by Tokyo Chemical Industry Co., Ltd., Catalog No. T0836), which was a supporting electrolyte, was dissolved in the solvent such that the concentration of tetra-n-butylammonium perchlorat…

The synthetic route of 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; US2012/330025; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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 4857-06-1

(5) 0.078 mol of 2-chlorobenzimidazole was dissolved in 90 mL of dry N,N-dimethylformamide, and 0.079 mol of 60% sodium hydrogen was added in portions in an ice bath and under a nitrogen atmosphere, followed by an ice bath. Stir for 30 minutes under nitrogen atmosphere, add 0.079 mol of 2-(trimethylsilyl)ethoxymethyl chloride, react at 20C for 16 hours, and turn the reaction solution into a yellow suspension, ice bathUnder cooling, 200 mL of water was slowly added, extracted with ethyl acetate, the organic phases were combined, and after drying, petroleum ether: ethyl acetate was used as eluent at a volume ratio of 10:1 to separate 16 g of white solid compound VII. The yield was 71.93%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; He Xu; Hu Yongzhu; Zhang Chi; Liu Chun; Cui Xilin; (26 pag.)CN107663192; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, SDS of cas: 288-32-4

Step A: 4-chloro-1H-imidazole To a solution of 1H-imidazole (10.0 g, 0.15 mol) in chloroform (100 mL) was slowly added a solution of chlorine (2.08 g, 0.0294 mol) in chloroform (18.6 mL). The reaction was cooled to 0 C., then left stirring overnight, gradually warming to room temperature. Aqueous sodium bisulfite was added and the layers were separated. The aqueous was extracted with ethyl acetate (3*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-10% methanol/dichloromethane) gave 4-chloro-1H-imidazole (400 mg) as a light yellow solid. 1H NMR (400 MHz, CD3OD, delta): 7.58 (s, 1H), 7.05 (s, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PFIZER INC.; US2012/202834; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, HPLC of Formula: C19H13BrN2

A mixture of compound 1a (1.745 g, 5.0 mmol),(1.91 g, 7.5 mmol) and KOAc (1.47 g, 15.0)Was dissolved in anhydrous 1,4-dioxane (40 mL)After nitrogen replacement,Pd (dppf) Cl2 (0.18 g, 0.25 mmol) was added,Heated to reflux for 3h.After completion of the reaction, the mixture was cooled to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4 and the solvent was removed by steaming.The final crude product was purified using n-hexane / ethyl acetate (v / v = 1: 3) SiO2 column,A white powdery solid was obtained.Yield: 1.88 g, 95%.

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, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China University of Mining and Technology; Ni Zhonghai; Zhang Ran; Zhang Lifang; Zhao Yun; (20 pag.)CN106905242; (2017); A;,
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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17325-26-7

b) 3-(3-Acetoxy-7-chloro-2,2-dimethyl-indan-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of acetic acid 4-chloro-3-hydroxy-2,2-dimethyl-indan-1-yl ester (1.55 g, 6.1 mmol) in THF (30 mL) is added methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.53 g, 12.2 mmol), and triphenylphosphine (3.2 g, 12.2 mmol). The reaction is cooled to 0 0C and di-f-butyl azodicarboxylate (2.81 g, 12.2 mmol) is added. The reaction is placed at room temperature and permitted to stir for ca. 12 hours and then is heated to 40 0C for 1.5 hours. The reaction mixture is cooled to 0 0C, quenched with 4 N HCI in dioxane (20 ml_, 80 mmol), and stirred for 30 minutes. The reaction is concentrated to near dryness and diluted with ethyl acetate. The organic layer is extracted three times with 1 N aqueous HCI. The aqueous extracts are combined, neutralized with Na2CO3, and extracted three times with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1 :3) to furnish 3-(3-acetoxy-7-chloro-2,2-dimethyl-indan-1- yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 332.04 (M+H)+.

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 17325-26-7.

Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-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 33468-69-8, SDS of cas: 33468-69-8

Example 5: Preparation of Compound 25A microwave vial was charged with Intermediate F (20 mg, 0.044 mmol), 4-(trifluoromethyl)- lH-imidazole (20 mg, 0.15 mmol), CS2CO3 (43.2 mg, 0.133 mmol) and DMA (500 mu). The mixture was heated at 150C under microwave irradiation for 3 h. The mixture was then purified by reverse-phase preparative HPLC (0: 100 to 95 :5 MeCN:water: 0.1% v/v TFA modifier) to afford 1-25 as the TFA salt. ‘H NMR (500 MHz, DMSO-d6) delta = 8.68-8.20 (m, 4H), 5.00 (s, 1H), 4.55-4.38 (m, 1H), 4.22-4.16 (m, 1H), 4.12 (q, 3=1 A, 2H), 3.35-3.24 (m, 1H), 3.22-3.01 (m, 2H), 2.33-2.21 (m, 1H), 2.21-2.09 (m, 1H), 1.30 (d, /=6.9, 5H), 1.24 (t, /=7.2, 3H). MS (EI) Calc’d for C20H24F3N10 [M+H]+, 461; found 461.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem