Category: imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

(2) Synthesis of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid Ethyl diethylphosphonoacetate (5.7 g) and lithium hydroxide monohydrate (1.3 g) were sequentially added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5.0 g) in THF (20 mL) and ethanol (5 mL), and the reaction solution was stirred at room temperature for nine hours. A 2 N sodium hydroxide solution (20 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was cooled to 0 C., and 2 N hydrochloric acid (20 mL) was added to the reaction solution. The resulting precipitate was collected by filtration. The resulting precipitate washed with water and ethyl acetate to obtain 5.1 g of the title compound. The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 2.15 (s, 3H), 3.88 (s, 3H), 6.66 (d, J=16.0 Hz, 1H), 7.16 (s, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.56 (s, 1H), 7.60 (d, J=16.0 Hz, 1H), 7.81 (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; Eisai R&D Management Co., Ltd.; US2007/219181; (2007); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Ethyl 1H-imidazole-2-carboxylate

Ethyl 1-amino-1H-imidazole-2-carboxylate To a stirred suspension of ammonium chloride (228 g, 4.28 mol) in MTBE (2.4 L), aq. NH3 (1.2 L) was added at -20 C., prior to the addition of 11-14% sodium hypochlorite (3.5 L, 4.79 mol) at the same temperature over a period of 30 min. The reaction mixture was stirred at the same temperature for 1 h, after which the MTBE layer was separated and washed with brine solution. MTBE layer was dried over Na2SO4 and kept in the refrigerator and used immediately. In an another flask NaH (20 g, 513.9 mmol) was suspended in DMF (600 mL) at -10 C., to which a solution of ethyl 1H-imidazole-2-carboxylate (60 g, 428.2 mmol) in DMF (150 mL) was added slowly. The reaction mixture was stirred at room temperature for 1.5 h and cooled to -20 C., prior to the drop-wise addition of the chloramine solution in MTBE. The reaction was stirred at -10 C. for 1 h and at room temperature for 2 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 0 C. and quenched with 1 L of 10% Na2S2O3 solution. Organic layer was separated; and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered and evaporated to get crude ethyl 1-amino-1H-imidazole-2-carboxylate as a solution in DMF, which was used in the next step as such. A small portion of the solution was dried in vacuo to remove DMF and the product was characterized by 1H-NMR and LC-MS. ES+, m/z 156.3 [M+1].

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Polaris Pharmaceuticals; WEBBER, Stephen E.; TAO, Xueliang; BRIN, Elena; (85 pag.)US2017/369489; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 22884-10-2, A common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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.

Example 6:(Comparative) Preparation of Zoledronic Acid in PEG-400:[0025] Example 3 was repeated substituting PEG-400 (400ml) for diglyme. After the addition of phosphorus trichloride and increased temperature of the reaction mass, a solid formed that eventually returned to solution upon further heating. The yield of zoledronic acid was 7 % (isolated yield). 1HNMR (D2O/NaOD): 7.72 (s, 1 H); 7.22 (s, 1 H); 6.87 (s, 1 H); 4.82 (O-H, 7.02 H); 4.45 (m, 2 H). 31P NMR (D2O/NaOD): 17.0 (m). Not only was there a substantial decrease in yield, but the product purity deteriorated as well.

The synthetic route of 22884-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALBEMARLE CORPORATION; WO2007/109542; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. Product Details of 1450-93-7

1.1. 7-(pyrimidin-4-yl)-1 H-imidazo[1,2-a]pyrimidin-5-one A mixture containing 2.9g (15 mmol) of 3-oxo-3-(pyrimidin-4-yl)-propionic acid ethyl ester (prepared by analogy to the method described in patent DE 2705582), 2g (15 mmol) of 2-aminoimidazole hemisulfate and 1.2g (15 mmol) of ammonium acetate was heated at 140ØC during 18 h. The cooled mixture was treated with 30ml of acetonitrile and filtered and the precipitate was added to water and heated at reflux temperature for 30 min. The resulting solution was cooled and the precipitate recovered by filtration. The crude product thus obtained was recrystallised from ethanol to give 1.75g of pure product as a gray solid. Mp: 345-346ØC

The synthetic route of 1H-imidazol-2-amine sulfate(2:1) has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION; EP1340759; (2003); 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step B:; To a solution of 77.1 b (300 mg, 1.01 mmol) in THF (5 ml) was added ‘PrMgCI. LiCI (1 M in THF, 1.3 ml, 1.3 mmol) and stirred at room temperature for 10 min, followed with addition of 77.1c (216 mg, 1.01 mmol). The resulting mixture was stirred overnight, then quenched with saturated aqueous NH4CI, extracted with EtOAc (3 X). The combination of organic layers was washed with brine, dried (Na2SO4), concentrated and purified by flash chromatography to afford product 77.1 as colorless oil (210 mg, 48%). 1H NMR (CDCI3, ppm) 7.39-7.36 (m, 1 H), 7.31-7.25 (m, 3H), 7.20- 7.10 (m, 2H), 7.09-7.02 (m, 4H), 6.44-6.35 (m, 1 H), 6.28-6.20 (m, 1 H), 5.85 (d, 1 H), 3.89 (d, 3H), 2.47 (s, 3H), 1.75-1.70 (m, 3H); MS (ES-LCMS, M+1 ) 434.2. Retention time: 2.55 min.

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/32277; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 25 ml round bottom flask is added 4 – nitroimidazole (0.052 g, 0 . 461 mmol), potassium carbonate (0.152 g, 1 . 10 mmol), for 10 ml b the nitrile does solvent 60 C under stirring 1 hour later, adding imidazole and benzo thiazole derivatives VI – 6 (0.2 g, 0 . 423 mmol), continue to 60 C under stirring reaction, thin-layer chromatography tracking until a reaction is finished. Removing the acetonitrile is distilled under reduced pressure, then the saturated salt water and chloroform extraction, concentrate, column chromatography, recrystallization, post-treatment such as drying to obtain compound II – 6 (0.176 g), yield 83.0%; white solid

The synthetic route of 5-Nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Zhou Chenghe; Ma Dili·siweita·kaweisiwarui; Li Zhenzhen; (24 pag.)CN108383859; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10351-75-4,Some common heterocyclic compound, 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, molecular formula is C9H6N2O4, 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 reaction mixture of MnCl2 (0.2 mmol, 25.2 mg), H3bidc(0.1 mmol, 20.6 mg), and phen (0.1 mmol, 19.8 mg), H2O(4mL) and DMF (4 mL) was stirred for half an hour, thentransferred and sealed in a 10 mL glassflask. The system washeated in an oven at 85C for 24 hours and cooled to roomtemperature. Accordingly colourless block crystals were isolated by filtering, washed with distilled water and dried at inair. The yield of colorless crystalline product was 58% (basedon Mn). Anal. Calcd for C9H6N2O5Mn: C, 38.98; H, 2.17;N, 10.10%. Found: C, 38.85; H, 2.04; N, 10.02%. IR (KBrcm1): 3398(s), 3119(s), 1548(s), 1412(s), 1270(w), 1176(s),1122(s), 959(m), 876(m), 804(m), 629(w), 589(w), 429(m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, its application will become more common.

Reference:
Article; Zhang, Huijie; Zhou, Guangpeng; Fan, Ruiqing; Wang, Xinming; Yang, Yulin; Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry; vol. 46; 8; (2016); p. 1224 – 1235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 solution of 5-bromo-1-methyl-1H-imidazole (25.0 g, 155 mmol; dried over 3 A molecular sieves, then filtered) in DCM (310 mL) was stirred on an ice bath while iPrMgCl (72 mL, 2.01 M solution in THF, 145 mmol) was added rapidly dropwise under argon via pressure-equalizing addition funnel. Residual iPrMgCl was rinsed down with 50 mL THF, and the ice bath was removed and the reaction stirred for 25 minutes. A solution of tert-butyl 4-formylpiperidine-1-carboxylate (27.6 g, 130 mmol) (PharmaCore) in THF (65 mL) was added dropwise over ?5 minutes via pressure-equalizing addition funnel at room temperature. After stirring 1 hour at room temperature, the yellow mixture was quenched with 5 M aqueous NH4Cl (250 mL) in one portion. The organic layer was dried (Na2SO4), filtered, and concentrated to provide the crude title compound as a clear light amber oil.

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

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Pierce, Joan; Goldberg, Steven; Fourie, Anne; Xue, Xiaohua; US2014/107094; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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. Recommanded Product: 1-(1H-Benzo[d]imidazol-2-yl)ethanone

General procedure: To the solution of 2-acetyl benzimidazole 1 (0.01 mol) in MeOH (20 mL) was added 10% aqueous NaOH (2 mL) at 0C with stirring. Then, the solution of aromatic aldehydes (0.01 mol) in MeOH was added drop-wise. The reaction mixture was magnetically stirred for 12 h. After completion of the reaction (monitored by TLC) the reaction mixture was poured over crushed ice. The separated solid was filtered, washed with water and dried. The residue was purified by column chromatography (silica gel with 10% ethyl acetate in petroleum ether) to afford pure benzimidazole derived chalcone 2a-m.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-70-8, its application will become more common.

Reference:
Article; Meshram, Gangadhar A; Vala, Vipul A.; Wagh, Pramod A.; Deshpande, Shruti S.; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 5; (2016); p. 613 – 623;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 7152-24-1, 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. 7152-24-1 name is 2-(Methylthio)benzimidazole, 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 following compound was prepared from 2-(3-nitrophenylamino)-benzoyl chloride and 2-methylthiobenzimidazole: 5-(3-nitrophenyl)-benzimidazo-[2,1-b]-quinazolin-12(5H)-one STR14 Yield: 62% of theory, melting point 294 C.; N calculated 15.72%; N found 15.73%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Methylthio)benzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; Troponwerke GmbH & Co.; US4539402; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem