Category: imidazoles-derivatives

Application of 95470-42-1, 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. 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

(1) Ethyl 2-bromo-4-methyl-1 H-imidazole-5-carboxylate (2.75 g, 11.81 mmol) described in Example 1(1) was dissolved in DMF (20 mE), potassium carbonate (3.26 g, 23.62 mmol) and 2,5-dichlorobenzyl bromide (3.4 g, 14.17 mmol) were added thereto, and the mixture was stirred at 90° C. for 3 hours. Afier the reaction, water (50 mE) was added and the mixture was extracted twice with ethyl acetate (50 mE). The organic layer was washed with saturated aqueous sodium chloride and subsequently dried over sodium sulfate. After concentrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-1 -(2,5- dichlorobenzyl)-4 -methyl-i H-imidazole-5-carboxylate(1.72 g):10160] ?H-NMR (CDC13) oe: 7.34 (1H, d, J=8.8 Hz), 7.20(1H, dd, J=8.8, 2.4 Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s),4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz);10161] ESI-MS mlz=391 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); 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. 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Bromophenyl)-1H-imidazole

Step K 1-(4-Toluenesulfonyl)-2-(2-bromophenyl) imidazole A solution of 2.50 g (11.6 mmol) of 2-(2-bromophenyl)imidazole in 10 mL of methylene chloride was treated with 1.9 mL of triethylamine (13.8 mmol), 2.64 g (13.8 mmol) of p-toluenesulfonyl chloride and 100 mg of 4-dimethylaminopyridine. The reaction mixture was stirred at room temperature for 15 minutes then transferred to a separatory funnel and washed with water, 5percent aqueous citric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and solvents removed under vacuum. The crude product was chromatographed on silica, eluding with hexane/ethyl acetate (1:1), to give 4.16 g (11.0 mmol 95percent) of the product which was recrystallized from hexane. FAB-MS: calculated for C16 H13 BrN2 O2 S 376,378; found 377,379 (M+H, 50percent). 1 H NMR (200 MHz, CDCl3): 2.32 (s, 3H), 7.09 (d, 2 Hz, 1H), 7.12 (d, 8 Hz, 2H), 7.28 (m, 5H), 7.46 (m, 1H), 7.57 (d, 2 Hz, 1H).

The synthetic route of 162356-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5583130; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4,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.

General procedure: In a 100 mL round bottom flask, Cu-grafted catalyst (0.05 g), aryl-boronic acid (1 mmol), N-H heterocycles (1.2 mmol), and 10 mLmethanol were stirred under nitrogen atmosphere, at 40C. Thereaction mixtures were collected at different time interval and identified by GC-MS and quantified by GC analysis. After the com-pletion of the reaction, the catalyst was filtered off and washedwith water followed by acetone and dried in oven. The filtrate wasextracted with ethyl acetate (3 × 20 mL) and the combined organiclayers were dried with anhydrous Na2SO4by vacuum. The filtratewas concentrated by vacuum and the resulting residue was puri-fied by column chromatography on silica gel to provide the desiredproduct.

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

Reference:
Article; Islam, Sk.Manirul; Salam, Noor; Mondal, Paramita; Roy, Anupam Singha; Ghosh, Kajari; Tuhina; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 7 – 19;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

REFERENCE EXAMPLE 8 (+)-4,5,6,7-tetrahydrohenzimidazole-5-carboxylic acid hydrochloride Methyl benzimidazole-5-carboxylate was subjected to catalytic reduction according to the method described in CROATICA CHEMICA ACTA 45, 297-312 (1973), to obtain methyl 4,5,6,7-tetrahydrobenzimidazole-5-carboxylate.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Tanabe Company Limited; US5677326; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

68282-53-1, Adding some certain compound to certain chemical reactions, such as: 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, 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 68282-53-1.

COMPOUND 12.1. 20: 4- {5. 8-DIMETHOXY-2-rf4-METHYL-l-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}-N,N- DIETHYLBENZAMIDE; INTERMEDIATE 5.1. 10 (115 mg, 0.31 mmol) and 4-methyl-5- imidazolecarbaldehyde (108 mg, 0.62 mmol) were dissolved in DCE (5.0 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (197 mg, 0.93 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman 1PS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (103 mg, 0. 20 mmol, 65%).’H NMR (500 MHz, CDC13) : 8 0. 99, 1.18 (2 brs, 6H), 2.58-2. 74, 3.17-3. 50 (2 m, 8H), 3.32, 3.35 (2 s, 6H), 3.44, 3.65 (2 d, J 12.0 Hz, 2H), 5.05 (s, 1H), 6.51, 6.63 (2 d, J 9. 0 Hz, 2H), 6.87 (s, 1H), 7.00, 7.14 (m, 4H), 7. 21 (m, 5H), 7.80 (d, J 3. 5 Hz, 2H).

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 68282-53-1.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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: An equimolar mixture (1.0 mmol) of thecorresponding 2-amino-4-arylimidazole 1, aromatic aldehyde 2and Meldrum?s acid 3 was refluxed in iPrOH (3 mL) for3-5 min. After cooling, the solid products 4 were filtered off,washed with iPrOH and dried on air. 4a: colourless solid, 77%;mp 243-245 C; IR (KBr, cm-1) nu: 3404-2800 (NH2, NH, OH),1684 (C=O); 1H NMR (200 MHz, DMSO-d6) delta 12.27 (br s, 2H,NH, OH), 7.61-7.49 (m, 2H, Harom), 7.48-7.31 (m, 5H, Harom),7.27-7.01 (m, 5H, NH2,, Harom), 5.48 (s, 1H, CH), 1.51 (s, 6H,CH3); 13C NMR (125 MHz, CDCl3) delta 166.8 (C=O), 146.6(C-OH), 144.0, 129.4, 128.9, 128.4, 128.3, 127.5, 127.4, 127.2,125.9, 121.1, 100.6, 76.0 (C=COH), 35.1 (CH), 26.4 (CH3),25.9 (CH3); MS (m/z) (%): 289 (76), (391 [M+?] – 44 -58), 247(53), 159 (36), 104 (19), 77 (8), 44 (39), 43 (100); anal. calcdfor C22H21N3O4 (391.5) C, 67.52; H, 5.37; N, 10.74; found: C,68.77; H, 5.93; N, 10.79.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4, 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. 288-32-4 name is 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.

The starting material was prepared as follows: Imidazole (20.4 g, 300 mmol) and ethylene carbonate (28.6 g, 325 mmol) were heated at 125 C. for 1 hour. Once the CO2 evolution had ceased the reaction mixture was allowed to cool to ambient temperature, was suspended in methylene chloride/methanol (10/1, 50 ml) and was placed on the top of a short plug of silica. Elution was done using an increasingly polar solvent mixture of methylene chloride/methanol (100/10 up to 100/15). Removal of the solvent by evaporation gave crude 2-(imidazol-1-yl)ethanol (20.1 g, 60%).

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

Reference:
Patent; Zeneca Limited; US6294532; (2001); B1;,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, A new synthetic method of this compound is introduced below., Computed Properties of C5H8N2O

Add sodium hydride (0.79 g; 1.1 equiv; 19.75 mmoles) slowly to a 0 C. solution of 1H-imidazole-1-ethanol (2.01 g; 1.0 equiv; 17.93 mmoles) in tetrahydrofuran (90 mL). Stir for 1 hour, then add acetic acid, bromo-, 1,1-dimethylethyl ester (4.03 mL; 1.49 equiv; 26.76 mmoles) dropwise at 0 C. Warm the solution to ambient temperature and stir for 3 hours, then add 250 mL saturated aqueous sodium bicarbonate solution. Extract the mixture with dichloromethane (3*150 mL). Wash the combined organic extracts with brine (100 mL), dry over sodium sulfate, filter, and concentrate to afford the crude product. Purify this residue by column chromatography (0 to 20% methanol in dichloromethane) to afford tert-butyl 2-(2-imidazol-1-ylethoxy)acetate (0.85 g; 21%) as a viscous yellow-brown oil: MS (m/z): 227(M+1).

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; Eli Lilly and Company; Beauchamp, Thomas James; Dao, Yen; Jones, Spencer Brian; Norman, Bryan Hurst; Pfeifer, Lance Allen; US2014/200231; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-1H-imidazole, molecular formula is C6H10N2, 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.

Take a 100 mL two-necked flask, add N-propyl imidazole (2.17 g, 19.0 mmol), 35 mL toluene,3-Bromopropyldiphenylphosphine oxide (6.46 g, 20.0 mmol) was added dropwise with heating and stirring; the reaction was carried out at 85°C for 8 h and cooled to room temperature. The upper layer of toluene is poured out, and 100 mL of deionized water is added to dissolve the product to obtain an aqueous phase.The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL x 4) to separate the aqueous phase two;Di(2-ethylhexyl)phosphate (P204) (6.12 g, 19.0 mmol) was refluxed for 23 h under sodium.The resulting sodium salt was dissolved in dichloromethane and the previously separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. Wash the organic phase with deionized water (20 mL x 5)Separate the organic phase two, add anhydrous Na2SO4 to dry the organic phase two, filter,The majority of CH2Cl2 was evaporated under reduced pressure and vacuum dried at 70°C for 3 hours.The pale yellow viscous liquid was 10.93 g (yield 90percent),

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

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem