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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 144689-93-0

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); 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. 1072-62-4, name is 2-Ethyl-1H-imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C5H8N2

2-Ethyl imidazole (1.01 g, 10.5 mmol) dissolvedin acetonitrile (25 mL) was combined with potassium hydroxide (0.58 g, 10.3mmol) and stirred for 30 minutes at 80C. 2-(Bromomethyl)naphthalene (1.73 g, 7.8 mmol) was added and the mixture wasstirred and heated at 80C overnight. The reaction mixture was filtered toremove a white solid (presumed to be potassium bromide) and the volatiles wereremoved from the filtrate to yield a yellow oil. The oil was suspended withdichloromethane (40 mL) and washed with a basic aqueous solution (1 x 30 mL)and water (3 x 30 mL). The organic layers were dried with magnesium sulfate andconcentrated to a yellow oil. The oil was resuspended in acetonitrile (7 mL)and 2-(chloromethyl)quinoline (1.59 g, 9.0 mmol) was added to the solution. Themixture was stirred and heated at 80C overnight. A white solid precipitatedfrom the hot acetonitrile and was filtered, washed with acetonitrile, and driedin air to yield 4-Cl (0.850 yield). MP = 204-207C. HRMS (ESI+) calcd for C26H24N3+[M-Cl] of m/z = 378.1965, found m/z = 378.2000. 1H NMR (500 MHz,DMSO- d6) delta = 8.48 (1H, d,Ar, J = 8.8 Hz), 8.03 (2H, t, Ar, J = 8.3 Hz), 7.98 (1H, m, Ar), 7.93 (3H, m,Ar), 7.90 (1H, m, Ar), 7.76 (2H, m, Ar), 7.64 (2H, m, Ar), 7.58 (2H, m, Ar),7.50 (1H, m, Ar), 5.90 (2H, s, CH2), 5.76 (2H, s, CH2),3.17 (2H, q, CH2, J = 7.6 Hz) 0.93 (3H, t, CH3, J = 7.6Hz). 13C NMR (125 MHz, DMSO- d6)delta = 154.2 (Ar), 149.1 (Ar), 146.7 (Ar), 137.4 (Ar), 132.7 (Ar), 132.5 (Ar),132.5 (Ar), 130.1 (Ar), 128.7 (Ar), 128.3 (Ar), 128.0 (Ar), 127.7 (Ar), 127.7(Ar), 127.2 (Ar), 126.9 (Ar), 126.7 (Ar), 126.6 (Ar), 126.4 (Ar), 125.0 (Ar),123.1 (Ar), 122.2 (Ar), 119.9 (Ar), 52.2 (CH2), 50.8 (CH2),16.6 (CH2), 11.2 (CH3). Crystal data for 4-Cl?H2O: C26H26N3O1Cl1,M = 431.95, Monoclinic, a =34.6333(13) A, b = 9.5796(4) A, c = 13.6475(5) A, beta = 92.286(2), V = 4524.8(3) A3, T = 100(2) K, space group C2/c, Z= 8, 16910 reflections measured, 4589 [R(int) = 0.0411]. The final R1 values were 0.0475 (I > 2sigma(I)). The final wR(F2)values were 0.1118 (I > 2sigma(I)).The final R1 values were0.0650 (all data). The final wR(F2) values were 0.1215 (alldata).

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; DeBord, Michael A.; Wagers, Patrick O.; Crabtree, Steven R.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 2; (2017); p. 196 – 202;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 3-tert-butyl-5-bromomethyl-2-hydroxybenzaldehyde [46,47] in toluene (5.0 mL) was addeddropwise to a solution of N-alkylimidazole (10.0 mmol) in toluene(20.0 mL) over 10 min at room temperature. The mixture was thenheated to reflux for 5 h. After cooling to room temperature, the pre-cipitate product was filtered, washed with toluene (3 × 5 mL) anddried under reduced pressure.

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, 1-Octyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Duan, Shuhui; Jing, Xinyao; Li, Dandan; Jing, Huanwang; Journal of Molecular Catalysis A: Chemical; vol. 411; (2016); p. 34 – 39;,
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. 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, A new synthetic method of this compound is introduced below., Recommanded Product: 2466-76-4

Add 1-acetylimidazole (0.035 g, 0.315 mmol) and triethylamine (0.04 mL, 0.286 mmol) to solution of 2-(R)-[2-(S)-amino-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]- piperidine-1-carboxylic acid tert-butyl ester (0.106 mg, 0.286 mmol) in dichloromethane (10 mL) and stir 18 h at room temperature. Dilute with ethyl acetate and wash with 1 N hydrochloric acid (3x), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with dichloromethane and ethyl acetate) to give the title compound as a white solid (0.089 g, 76percent). MS (ES): m/z = 411.2 [M-H].

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/108358; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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. COA of Formula: C3H4N2

General procedure: A mixture of imidazole (22 mmol, 1 equiv) and the alkyl bromide (1equiv) in toluene (30 mL) in the presence of tetraethylammonium iodide(0.2 equiv) and sodium hydroxide (3 equiv) was heated at refluxtemperature for 10 h. The resulting mixture was cooled to room temperature,water was added, and the mixture extracted twice with ethylacetate. The combined organic extracts were washed with brine, driedover sodium sulfate, and concentrated. Purification by flash-columnchromatography on silica gel using ethyl acetate as an eluent, followedby drying under high vacuum gave the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Article; Brockhausen, Inka; Kocev, Alexander; Kong, Xianqi; Melamed, Jacob; Szarek, Walter A.; Vlahakis, Jason Z.; Wang, Shuo; Xu, Yaozu; Bioorganic and medicinal chemistry; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 621-72-7, 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. 621-72-7, name is 2-Benzyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Metallic Na (76 mg,3.3 mmol) was added to t-BuOH (30 ml), and the mixturewas heated under reflux until effervescence ceased. Thenazole 3b-d or 6b,d,e (3 mmol) and 3,5-dibromo-1-(1,1-dioxidothietan-3-yl)-1H-1,2,4-triazole (1) (0.99 g, 3 mmol)were added. The reaction mixture was heated under refluxfor 2 h (for compounds 4b-d, 7d,e) or 3 h (for compound7b). The solvent was evaporated under reduced pressure,and H2O (15 ml) was added to the residue. The precipitatewas filtered off, dried at 60C, and recrystallized from asuitable solvent.

The synthetic route of 2-Benzyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Makarova, Nadezhda N.; Klen, Elena E.; Khaliullin, Ferkat ?.; Chemistry of Heterocyclic Compounds; vol. 55; 9; (2019); p. 823 – 826; Khim. Geterotsikl. Soedin.; vol. 55; 9; (2019); p. 823 – 826,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]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 705-09-9, SDS of cas: 705-09-9

Compound 2 (425 muetaetaomicronIota, 1.0 eq.) is dissolved in DMF (2 ml) and cooled to -5C, treated with anhydrous potassium carbonate (1 .44 eq.) and 2-(difluoromethyl)-1 H-benzo[c/]- imidazole (1 .4 eq.), stirred for 30 min and further stirred at room temperature for 4 h. The reaction mixture is diluted with water and the precipitate is filtered and washed with small amounts of water. Purification is done by silica gel flash column chromatography. Rf: 0.72 (methylene chloride/methanol, 95:5 v/v); 1H NMR (CDCI3, 400 MHz) delta 8.43 (d, J = 7.8 Hz, 1 H), 7.90 (d, J = 7.6 Hz, 1 H), 7.71 -7.43 (m, 3H), 4.00-3.95 (m, 4H), 3.86-3.80 (m, 4H); 19F NMR (CDCI3, 400 MHz) delta -1 19.20 (d, J = 53.9 Hz, 2F).

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-(Difluoromethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF BASEL; CMILJANOVIC, Vladimir; CMILJANOVIC, Natasa; GIESE, Bernd; WYMANN, Matthias; WO2011/135520; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-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.

2-Chloro-5,6-dibromobenzimidazole (17) To a suspension of 0.763 g (5 mmole) of 2-chlorobenzimidazole in 50 mL of 1:1 MeOH/H2 O, was added dropwise a solution of 1 mL of Br2 in 10 mL of MeOH over a period of 30 min. The reaction mixture was stirred at room temperature overnight and was then filtered. The solid was washed with portions of H2 O until the washings were neutral. This solid was air dried and recrystallized from MeOH to give 1.115 g (3 crops, 72%) of 17. mp 228 C.; 1 H NMR (DMSO-d6) d 13-14 (br. s, 1,1-NH), 7.93 (s, 2,4-H, 7-H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8, 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 33468-69-8 as follows.

Sodium hydride (7.91 mg, 0.198 mmol, 60% in mineral oil) was added to a solution of 4- (trifluoromethyl)-I H-imidazole (24.46 mg, 0.180 mmol) in dry N,N-dimethylformamide (0.4 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased. A solution of 2-(5- bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-(trifluoromethyl)pyridine (66.0 mg, 0.180 mmol) in N,N-dimethylformamide (2.0 ml) was slowly added and the reaction mixture stirred at room (0511) temperature for 30 minutes. Two more equivalents of the previously described solution consisting of sodium hydride and 4-(trifluoromethyl)-1 H-imidazole were then added and stirring continued overnight at 60C. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate) to afford 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (compound P2) as a solid (55 mg). LCMS (method 4): 423 (M+H)+, retention time 0.97 min. H-NMR (CDCb, ppm) 8.70 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H), 7.71 (m, 1 H), 3.81 (s, 3H), 3.06 (q, 2H), 1.42 (t, 3H).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; EDMUNDS, Andrew; RENOLD, Peter; BUCHHOLZ, Anke; (96 pag.)WO2018/41729; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C12H11N3O

3-Methoxy-4-(4-methyl-lH-imidazol-l-yl)benzonitrile (100 mg, 0.469 mmol) was placed in a reaction vessel, and a 5 M aqueous sodium hydroxide solution (1 mL) and methanol (2 mL) were successively added to the vessel. The resultant mixture was stirred at room temperature for 2 hours, and then further stirred at 65C for 5 hours. The resultant reaction mixture was concentrated under a reduced pressure, and a 2 M aqueous hydrochloric acid solution (4 mL) and water (4 mL) were successively added to the concentrate. The solids collected by filtration were dried under a reduced pressure to obtain 98 mg of a title compound. Yield: 78%.

The synthetic route of 1243204-92-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management CO., LTD.; YOSHIKAWA, Seiji; KAYANO, Akio; WO2011/37244; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem