Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 621-72-7, name is 2-Benzyl-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 621-72-7, Recommanded Product: 621-72-7

To the reaction vessel was added 8.2 g of dibazole,63 g of 10 wt% hydrochloric acid solution and 1.2 g of activated carbon,Air was introduced into the reaction vessel while stirring, and the temperature was raised to 95 C.The reaction was stirred for 10 hours while the reaction was completed, and the air was stopped.Drop to 15 C, filter, and evaporate the filtrate under reduced pressure to give 8.5 g of crude material;The crude product was mixed with 70 g of anhydrous methanol and stirred and dissolved at 55 C.The mixture was filtered while hot, and the filtrate was stirred at 0 C for 3 hours, and filtered.Drying, 7.8 g of diazol oxidized impurity reference substance was obtained, and the yield was 89.3%.The purity was determined by HPLC to be 99.95%.

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

Reference:
Patent; Wuhan Xian Lu Pharmaceutical Technology Co., Ltd.; Huang Li; Ning Fan; Wu Bo; Wang Ge; Xie Shuwei; Chen Weijiang; (6 pag.)CN108863946; (2018); A;,
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. 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-(4-Nitrophenyl)-1H-imidazole

General procedure: To a stirring solution of 4-CNPy (104 mg, 1.0 mmol, 2 equiv) in ethanol (25 ml), Ru(NO)Cl3·2H2O (136 mg, 0.5 mmol, 1 equiv) was added and contents of the flask heated under reflux for 12 h. After cooling to room temperature a red solid separated which was isolated by filtration, washed with ethanol, diethylether and dried under vacuo. Crystals suitable for X-ray diffraction analyses were obtained by slow diffusion of hexane into dichloromethane solution of the complex. Yield: 138 mg (62%),

The synthetic route of 2301-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Amit; Pandey, Rampal; Gupta, Rakesh Kumar; Ghosh, Kaushik; Pandey, Daya Shankar; Polyhedron; vol. 52; (2013); p. 837 – 843;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C8H6N2O2

General procedure: The aryl carboxylic acid (1.1 eq.) and TBTU (1.2) were suspended in anhydrous THF (11 mL/mmol eq.) at r.t. under N2 atmosphere. DiPEA (2.4 eq.) was then added dropwise to the reaction mixture,followed by the different (thieno[2,3-d]pyrimidin-4-yl)-hydrazine (8a-d or f-i) (1 eq.) dissolved in anhydrous THF (11 mL/mmol eq.). The mixture was stirred at r.t. for 4 h, then concentrated under vacuum. The residue was dissolved in EtOAc (30 mL/mmol eq.), washed with water (30 mL/mmol eq.), saturated NaHCO3 solution (30 mL/mmol eq.), and finally with brine (30 mL/mmol eq.). The organic phase was concentrated under vacuum after drying over MgSO4. The crude residue was purified by recrystallisation or flash column chromatography.

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:
Article; Bassetto, Marcella; Leyssen, Pieter; Neyts, Johan; Yerukhimovich, Mark M.; Frick, David N.; Brancale, Andrea; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 31 – 47;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1072-84-0, A common heterocyclic compound, 1072-84-0, name is 1H-Imidazole-4-carboxylic acid, molecular formula is C4H4N2O2, 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 a mixture of 1H-imidazole-4-carboxylic acid (5.00 g, 44.6 mmol, CAS1072-84-0) in MeOH (50 mL) was added SOCl2 (10.6 g, 89.2 mmol, 6.47 mL). The reaction mixture was stirred at 70 C. for 16 hours. On completion, the reaction mixture was concentrated in vacuo to give the title compound (5.60 g, 99% yield) as white solid. The residue was used to the next step directly without further purification. 1H NMR (400 MHz, DMSO-d6) delta 9.29-9.25 (m, 1H), 8.37 (s, 1H), 3.87 (s, 3H).

The synthetic route of 1072-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.

300 mg of 3 (1 eq., 0.55 mmol), 86 mg of 1 (1 eq., 0.55 mmol),326 mg of Cu(OAc)2·H2O, 18 mg of potassium iodide (0.2 eq.,0.11 mmol) and 6 mg of Pd(OAc)2 were dissolved in 3 mL of dimethylsulfoxide and 12 mL acetonitrile. The reaction vessel was set under anatmospheric pressure of carbon monoxide (CAUTION: highly toxic) andshortly warmed with a hot water bath (40 C). After 1 h the reactionmixture was taken up in EtOAc and washed with sat. NaHCO3 andwater. The combined aqueous solutions were washed with EtOAc andthe combined organic solutions were washed with brine, dried overMgSO4 and the solvent was removed under reduced pressure. The crudeproduct was dried in vacuo overnight. Purification was performed usingcolumn chromatography (EtOAc/petrol ether 9:1). Yield: 160 mg(40%). 1H NMR (500 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.65 (s, 1H), 8.41(s, 1H), 8.23 (s, 2H), 7.84 (s, 1H), 7.54 (dd, J = 8.9, 5.0 Hz, 1H), 7.45(t, J = 8.7 Hz, 1H), 7.38 (s, 1H), 7.28 (s, 1H), 6.15 (d, J = 6.6 Hz, 1H),5.30 – 5.19 (m, 2H), 4.52 (t, J = 10.9 Hz, 1H), 3.96 (s, 3H), 3.10 (dd,J = 23.1, 11.6 Hz, 2H), 2.23 (d, J = 11.4 Hz, 2H), 2.15 – 2.06 (m, 2H),1.73 (d, J = 6.6 Hz, 3H), 1.43 (s, 9H) ppm. ESI-MS (M + Na): calc:755.19 found: 755.39.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Berger, Walter; Bielec, Bjoern; Heffeter, Petra; Keppler, Bernhard K.; Kowol, Christian R.; Schueffl, Hemma; Terenzi, Alessio; Bioorganic Chemistry; vol. 99; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 87941-55-7, These common heterocyclic compound, 87941-55-7, name is 4-Bromo-1-trityl-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.

To a suspension of 3.00 g (7.71 mmol) of 4-bromo-1-trityl-1H-imidazoie in 30 ml of dioxane1.58 g (9.23 mmol) of 4-methoxymethyi boronic acid, 3.47 g (10.5 mmol) of cesiumcarbonate and 0.121 g (0.131 mmol) of tris-(dibenzylideneaceton)dipalladium are added, followed by 0.315 ml (0.308 ml) of a solution of 5 g of tri-t-buylphosphine in 25 ml of dioxane. The mixture is heated at 80C and stirred for 6.5 hours. After cooling to room temperature the suspension is diluted with dichloromethane and filtered, the filter cake washed with ethyl acetate and the filtrate concentrated to dryness. The residue is purified by flash chromatography on silica (40 – 63 urn particle size) with hexane / ethyl acetate 7:3, yielding 2.805 g of 4-(4-methoxymethyl-phenyl)-1-trityl-1H-imidazole, Rt = 4.659 min by HPLC on a nucleosil C18HD column with acetonitril + 0.05% TFA / water + 0.05% TFA, 20/80 to 100/0 over 6 min, 1.0 ml/min solvent flow. MS (API-ES, pos. scan): e/m = 431 (M+1).

Statistics shows that 4-Bromo-1-trityl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 87941-55-7.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/10591; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 84946-20-3, 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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-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.

EXAMPLE 43 Norastemizole. To a 25 mL 3-neck flask equipped with a thermometer, ref lux consenser and stir bar were added, under a nitrogen atmosphere, 822 mg (4.8 mmol) of Compound XVI, obtained according to the procedure of Example 6, and 0.93 mL (8.0 mmol) of lutidine. The mixture was heated to 120 C., whereupon a solution of 1.04 g (4 mmol., 1 eq.) of Compound X (Aldrich Chemical Co., Milwaukee, Wis.), 8 mmol of tetrabutylammonium fluoride (obtained from its 1.0M THF solution by distillation under vacuum with anhydrous toluene) and 4 mL of N-methylpyrrolidinone was added slowly over 2 h. The reaction mixture was allowed to stir at 120 C. for 2 h. High-performance liquid chromatography revealed >95% coversion to Compound XVIII. The reaction mixture was allowed to cool to ambient temperature, and slowly poured into a solution of 5% aqueous NaOH while stirring. The resulting suspension was allowed to stir at 0-10 C. for 30 minutes, and the resulting solid product was collected by vacuum filtration, washed with water (3*5 mL), and air dried for 30 minutes under vacuum to afford a crude mixture of Compound XVIII and 6% (HPLC) of migration product Compound XIX. NMR data for Compound XVIII: 1 H NMR (300 MHz, DMSO-d6) delta7.30-7.02 (6H, m two groups), 6.95 (1H, pseudo t, J=7.8, 2.3 Hz), 6.85 (1H, pseudo t, J=7.8, 2.3 Hz), 5.35 (2H, s), 4.33 (1H, pseudo d), 4.02 (1H, m), 3.83 (1H, pseudo d), 3.17 (1H, pseudo t), 2.75 (1H, pseudo t), 2.02 (3H, s), 2.0 (2H, m overlapped), 1.45 (2H, m); 13 C NMR (75 MHz, DMSO-d6) delta168.0, 163.0 and 159.7 (13 C-19 F coupling), 153.9, 142.8, 134.3, 133.5, 129.1, 129.0, 128.2, 120.5, 118.4, 115.5, 115.2, 107.9, 44.8, 43.7, 32.3, 31.5, 21.4. It is to be noted that under the same reaction conditions as above, but without the use of tetrabutylammonium fluoride, only 4.9% conversion (high-performance liquid chromatography) to Compound XVIII was achieved after 3 h at 120 C. In addition, without the use of tetrabutylammonium fluoride, the ratio of Compound XVIII:Compound XIX was 4:1. The mixture of Compound XVIII obtained above was placed in a 50 mL, 3-neck flask equipped with a thermometer, reflux condenser and stir bar. 5 mL of 6N hydrochloric were added, and the resulting mixture was heated to 110 C. and allowed to stir at that temperature for 5 h. After the reaction was complete (>98% conversion to norastemizole as shown by high-performance liquid chromatography), the reaction mixture was allowed to cool to room temperature, and 10 mL of toluene and 10 mL of water were added, with stirring.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Sepracor Inc.; US5817823; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 38993-84-9 as follows. Application In Synthesis of (1-Methyl-1H-imidazol-5-yl)methanol

To the solution of (1 -methyl- lH-imidazol-5-yl)methanol (570 mg, 5 mmol) in dioxane (50 niL) in a 250 mL round bottom flask, was added NCS (815 mg, 6 mmol). The resulting mixture was stirred at room temperature overnight. Dioxane was removed under vacuum.

According to the analysis of related databases, 38993-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 4857-06-1 as follows. Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole

Example 1N-(4-Fluoro-3-trifluoromethyl-benzyl)-N-(1-methyl-1H-benzimidazol-2-yl)-benzenesulfonamide (Compound No.15)Step A: 2-Chloro-1-methyl-1H-benzimidazoleTo a solution of 2-chloro-1H-benzimidazole (5.03 g, 33.0 mmol) in anhydrous DMF (33 mL) at 0 C. was added portion-wise 95% NaH (871 mg, 36.3 mmol). The ice bath was removed and the resulting mixture was stirred at room temperature for 1 h. Iodomethane (4.68 g, 33.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The resulting mixture was then diluted with water, and the resulting precipitate was collected by filtration and purified by recrystallization from hexane to yield 2-chloro-1-methyl-1H-benzimidazole. MS 167 (M+1)+

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jetter, Michele C.; Macielag, Mark J.; Xia, Mingde; Xu, Xiaoqing; US2011/3801; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

The synthetic route of 1-Methyl-1H-imidazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem