Month: March 2021

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. 40197-20-4, name is 5-Bromo-1H-benzo[d]imidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 40197-20-4

N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride (1.2 g) was added to a mixture of 5-bromo-1H-benzimidazol-2-carboxylic acid (1.0 g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0 g), 1H-benzotriazol-1-ol (840 mg),and N,N-dimethylformamide (10 ml: hereinafter, abbreviated as DMF), followed by stirring at room temperature overnight.A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by stirring atroom temperature for 1 hour, and the resulting solid was collected by filtration, followed by drying under reduced pressure.The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) while heating to reflux. Themixture was cooled to room temperature and then hexane (100 ml) was added thereto. The resulting solid was collectedby filtration, followed by drying under reduced pressure, thereby obtaining (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.4 g) as a solid.

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; Astellas Pharma Inc.; NAGASHIMA, Takeyuki; TSUJIMOTO, Susumu; (27 pag.)EP3231425; (2017); 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Isopropyl-1H-imidazole

43-a : Synthesis of 1-(4-chloro-2-nitrophenyl)-2-isopropyl-1H-imidazole A mixture of 1.01 g of 4-chloro-1-fluoro-2-nitrobenzene, 634 mg of 2-isopropylimidazole, 1.46 mL of N,N-diisopropylethylamine and 12 mL of acetonitrile was heated under reflux for 15 hours. The solvent was distilled off, water was added, and the reaction liquid was rendered acidic with diluted hydrochloric acid, followed by washing with diethyl ether. The aqueous layer was rendered alkaline with aqueous sodium hydroxide solution, and extracted twice with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and removed of the solvent by distillation to provide 0.98 g of the title compound. 1H-NMR(CDCls,delta):1.22(6H,d,J=6.9Hz),2.5-2.8(1H,m), 6.81(1H,d,J=1.2Hz),7.09(1H,d,J=1.5Hz),7.39(1H,d,J=8.5Hz), 7.71(1H,dd,J=2.3,8.5Hz),8.05(1H,d,J=2.7Hz) MS(m/z):267(M++2), 265(M+)

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 36947-68-9.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP2123301; (2009); 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. 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 67085-11-4

(1) 3 kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1-hydro-imidazole was dissolved in 30 kg of methylene chloride.3.5 kg of thionyl chloride was added dropwise at a rate of 1.5 ml/s at 20C and slowly warmed to 33C.The reaction was incubated for 1 hour, then refluxed at 60C for 1 hour, and slowly cooled to below 15C to obtain a reaction liquid;(2) In the reaction liquid obtained in step (1), add 10 C. water at a rate of 0.5 ml/s with stirring, and the volume ratio of the reaction liquid to water is 0.005:1, and then 1.0 to 1.5 kg/L. Add anhydrous sodium carbonate, suction filter, discard the solid,The liquid was concentrated at 55[deg.] C. until no dichloromethane was distilled off, dried and obtained.Upon detection, the yield of the product of this example was 99.18%. The target product and impurity levels were determined using HPLC and standards.The target product, 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole, was detected to be 99.17%.The content of 1-(1-chloro-4-(4-chlorophenyl)butan-2-yl)-1-hydro-imidazole is 0.53%.The 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole content was 0.12%.

The synthetic route of 67085-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Peng Kaifeng; Zhang Yingshuai; Wen Fengqiu; Li Sanxin; Gong Yun; Li Fujun; (10 pag.)CN105175338; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7,Some common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, molecular formula is C5H6N2O2, 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.

d) 3-(2,2-Dimethyl-4-oxo-1 ,2,3,4-tetrahydro-naphthalen-1 -yl)-3H-imidazole-4-carboxylic acid methyl ester; To a solution of 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2.87 g, 13.88 mmol) and methyl 4-imidazolecarboxylate (CASNo. 17325-26-7, 1.25 g, 9.72 mmol) in THF (80 ml.) at 0 0C is added triphenylphosphine (3.68 g, 13.88 mmol) and dimethyl azodicarboxylate (40% in toluene, 5.14 ml_, 13.88 mmol) and the cooling bath is removed. After 15 hours, the mixture is concentrated and the resulting residue is dissolved in ethyl acetate (250 ml.) and is extracted five times with 1 M aqueous HCI (40 mL portions). The acidic aqueous phases are cooled to 0 0C and the pH is adjusted to ca. 12 with 4M aqueous NaOH at 0 0C. The aqueous phase is then extracted three times with dichloromethane. The combined organic layers are dried over MgSO4 and filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (dichloromethane-methanol, 49:1) to give 3-(2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4- carboxylic acid methyl ester; MS: (ESI) m/z 299.0 (M+H)+; 1H NMR (400 MHz, CDCI3) delta ppm 0.97 (S, 3 H), 1.15 (s, 3 H), 2.63 (d, J=16.8 Hz, 1 H), 2.74 (d, J=16.8 Hz, 1 H), 3.93 (s, 3 H), 6.79 (s, 1 H), 7.02 (d, J=7.6 Hz, 1 H), 7.35 (s, 1 H), 7.47 (t, J=7.6 Hz, 1 H), 7.55 (td, J=7.6, 1.5 Hz, 1 H), 7.86 (s, 1 H), 8.13 (dd, J=7.6, 1.5 Hz, 1 H);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-imidazole-5-carboxylate, its application will become more common.

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

68892-07-9, name is Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate, 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. Safety of Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate

To a mixture of example 159 (60 mg, 0.125 mmol, 1 equiv), methyl 2-mercapto-l-methyl-lH-imidazole-5-carboxylate (30.2 mg, 0,176 mmol, 1.4 equiv) and PPh3 (46.2 mg, 0.176 mmol. 1.4 equiv) in toluene (0.35 mL) at 0 C was added dropwise diethyl azodicarboxylate (40 % wt in toluene, 80 muEpsilon, 0, 176 mmol. 1.4 equiv). The mixture was stirred at rt for 3 h, concentrated, and then purified by column to give 79 mg (100%) of intermediate 161a as a white solid.

The synthetic route of 68892-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, COA of Formula: C13H9N3

d) Compound 8-3 (3.0 g, 8.10 mmol), benzimidazolo[1,2-a]benzimidazole (1.85 g, 8.91mmol), and potassium phosphate (1.96 g, 16.2 mmol) were added to NMP (30 mL). Themixture was stirred at 190 C for 17 h. In addition, potassium phosphate (3.92 g, 32.4 mmol) was added there, and the mixture was stirred at the same temperature for 27 h. Af8-2 ter reaction mixture was cooled at room temperature, it was diluted with water to give asolid. The solid was collected by filtration, and it was washed with 300 mL of MeOH. Thecrude product was purified by by column chromatography on silica gel eluting with CH2CI2to yield 4.7 g (78%) of compound (B-29) as a white solid. LC-MS (m/z) 745.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; NISHIMAE, Yuichi; KOHLSTEDT, Julia; SCHAeFER, Thomas; NAGASHIMA, Hideaki; (114 pag.)WO2016/97983; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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. Recommanded Product: 137049-00-4

To a solution of intermediate 2.40 (20. mg, 0.078 mmol) and triethylamine (30 muL, 0.2 mmol) in dichloromethane (0.5 mL) at ambient temperature was added 1-methyl- 1H-imidazole-4-sulfonyl chloride (21 mg, 0.12 mmol). The resulting mixture was stirred for 18 h, then diluted with wet dimethyl sulfoxide (0.5 mL), filtered through Celite and purified via mass-directed isolation using ultra-performance liquid chromatography (21 mg, 68% yield).1H NMR (500 MHz, Acetonitrile-d3) d 8.64 (s, 1H), 7.70 (dd, J = 11.8, 2.4 Hz, 1H), 7.62 (d, J = 1.4 Hz, 1H), 7.54 (d, J = 1.4 Hz, 1H), 7.37 (t, J = 8.6 Hz, 1H), 7.22 (ddd, J = 8.8, 2.4, 1.2 Hz, 1H), 3.80 (ddd, J = 11.7, 3.7, 1.9 Hz, 1H), 3.71 (s, 3H), 3.63 (d, J = 12.1 Hz, 1H), 2.65 (t, J = 11.1 Hz, 1H), 2.58 (ddt, J = 10.8, 7.2, 3.5 Hz, 1H), 2.52 (td, J = 11.9, 3.0 Hz, 1H), 1.93- 1.89 (m, 1H), 1.85- 1.74 (m, 1H), 1.65- 1.52 (m, 1H), 1.52- 1.39 (m, 1H); AMM (ESI) m/z 401.0858 [calc for C16H19ClFN4O3S (M+H)+ 401.0850].

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; VAL-CHUM, LIMITED PARTNERSHIP; GRENIER, Melissa Carey; SMITH, Amos B., III; FINZI, Andres; DING, Shilei; CHAPLEAU, Jean-Philippe; (240 pag.)WO2020/28482; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-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.

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give the title compound.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1072-63-5, 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. 1072-63-5 name is 1-Vinyl-1H-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.

In a round bottom flask, bromoethane (4.07 g, 0.367 mol) was added dropwise to 1-vinylimidazole (2.10 g, 0.213 mol),The reaction was refluxed at 40 C for 16 hours.The yellow-white solid obtained by filtration was washed several times with ethyl acetate and dried in a vacuum oven.The ionic liquid monomer ViEtlmBr was obtained.Yield: 3.27 g (76%).

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

Reference:
Patent; Liaoning University; Xia Lixin; Wang Kaili; Jiang Yi; (16 pag.)CN108677211; (2019); B;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Example 5; Preparation of ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityl tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (100 g), N-(triphenylmethyl)-5-(4′-bromomethyl biphenyl-2-yl)tetrazole (250 g), potassium carbonate (170 g) & tetra butyl ammonium bromide (15 g) in acetone (2.5 L) were refluxed for 10-16 hours. Progress of reaction was monitor by HPLC. After completion of reaction, reaction mass was cooled and filtered to remove the salts. Inorganic salts were washed with acetone (300 mL). Acetone from combine the filtrate and washings was distilled. The residue obtained was crystallized in acetonitrile to get ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate (280 g).HPLC Purity=98.5%

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ramanjaneyulu, Gorantla Seeta; Mohan, Bandari; Ray, Purna Chandra; Sethi, Madhuresh Kumar; Rawat, Vijendra Singh; Krishna, Yerramalla Raja; Lakshminarayana, Vemula; Srinivas, Mamidi; US2009/281327; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem