Category: imidazoles-derivatives

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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, A new synthetic method of this compound is introduced below., name: 1,1′-Thiocarbonyldiimidazole

REFERENCE SYNTHETIC EXAMPLE 2; Synthesis of methyl l-hydrazinothiocarbonylpiperidine-4- carboxylate; To a solution of methyl isonipecotate (1.0 g, 7.0 mmol) in tetrahydrofuran was added thiocarbonyl diimidazole (1.24 g, 6.98 mmol) at room temperature, and the reaction solution was stirred at room temperature for1.5 hours and then stirred with hydrazine monohydrate(700 mg, 14.0 mmol) for 4 hours. After addition of saturated aqueous sodium chloride, the reaction solution was extracted with ethyl acetate and chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 114%) .Morphology: pale yellow solid LC/MS: condition 5, retention time 0.52 (min)LC/MS (ESI+)m/z; 218, [M+l] +

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; WO2006/62240; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 822-36-6, name is 4-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. Application In Synthesis of 4-Methyl-1H-imidazole

In a pressure tube with one end sealed, add 190 mg CuI (1 mmol), 1.64 g 4-methyl-1H-imidazole (20 mmol), 3.25 g Cs2CO3 (10 mmol), and after Nitrogen replacement, add 2.40 g 3-bromo-5-(trifluoromethyl)aniline (10 mmol), 350 mg 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (2 mmol) and 30 mL DMF was added into a flask. The mixture was stirred at 110 C. for 18 h under sealing. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by column chromatography to afford 2.19 g desired product (91%). 1H NMR (400 MHz, d-DMSO), delta 8.06 (s, 1H), 7.35 (s, 1H), 6.97 (s, 1H), 6.93 (s, 1H), 6.81 (s, 1H), 5.87 (br, 2H), 2.15 (s, 3H). MS (ESI), m/z: 242 (M++H+).

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

Reference:
Patent; Guangzzhou Institute of Biomedicine and Health, Chineses Academy of Sciences; Ding, Ke; Wang, Deping; Pei, Duanqing; Zhang, Zhang; Shen, Mengjie; Luo, Kun; Feng, Yubing; US2013/196985; (2013); 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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 4-Iodo-1-trityl-1H-imidazole

To a solution of 4-IODO-L-TRITYL-LH-IMIDAZOLE (1 eq) in THF at room temperature was added ethylmagnesium bromide (1.2 eq) under dry conditions. After stirring for 90 minutes, zinc chloride (1.2 eq) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (10%) and 5- bromo-2-methylpyridine (1.2 eq) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with a EDTA buffer (at approximately pH 9), NaCl, dried over sodium sulfate, filtered and concentrated. The crude product was disolved in ethanol and concentrated HCl was added to the solution at room temperature. The reaction mixture was heated in a 50C oil bath for 2 hours. Upon cooling, the reaction was filtered and washed with ethyl ether to yield 5- (1H- imidazol-4-yl) -2-methyl-pyridine (63%). MH+ (160)

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; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2, 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. 71759-89-2 name is 5-Iodo-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.

[0294] Sodium hydride (15.3 g, 385 mmol) was added to a mixture of 4-iodo-lH- imidazole (50 g, 257 mmol) in THF (150 mL) at 0 C. After stirring for 0.5 h, iodomethane (40.0 g, 282 mmol) was added to the solution and the resulting mixture was stirred at room temperature overnight under N2. TLC (DCM / EtOAc = 2/1, v/v) indicated that starting material was consumed and two new spots were formed. The reaction was quenched with MeOH (50 mL), then concentrated to dryness, the residue was purified by silica gel column (DCM / EtOAc = 10/1, v/v) to afford the desired product (higher Rf) (28 g, 52%) as a yellow solid. [0295] 1H NMR (400 MHz, CDCl3) d (ppm): 7.32 (s, 1H), 6.96 (d, 7= 1.2 Hz, 1H), 3.68 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Iodo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; HARVEY, Darren Martin; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; (246 pag.)WO2019/108824; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of 2-bromoethyl glucoside 2 (1.1 mmol) and the alkylated imidazole 4 (3.3 mmol) in xylene (2 mL) was heated to 125 °C for 1 h. The solvent was evaporated and the crude product was taken up in MeCN (10 mL) and extracted 4 times with hexane (60 mL) to remove remaining imidazole 4. The acetonitrile phase was concentrated under reducing pressure to provide the desired product 5 as a pale yellow syrup in ~95percent yield.

The chemical industry reduces the impact on the environment during synthesis 1-Octyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Salman, Abbas Abdulameer; Tabandeh, Mojtaba; Heidelberg, Thorsten; Hussen, Rusnah Syahila Duali; Ali, Hapipah Mohd; Carbohydrate Research; vol. 412; (2015); p. 28 – 33;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, The chemical industry reduces the impact on the environment during synthesis 57090-88-7, name is 1H-Imidazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

Step A. 1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-imidazole-4-carbonitrile 1H-imidazole-4-carbonitrile (300 mg, 3.22 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (662 mg, 3.385 mmol) were taken into anhydrous DMF (5 ml) and cooled to 0 C. Sodium hydride (150 mg, 3.7 mmol) was added to the solution portionwise and stirred at room temperature for 2 hours. The reaction was quenched with saturated ammonium chloride (10 ml) followed by evaporation of the solvent in vacuo. The residue was suspended in dichloromethane (20 ml) and water (20 ml). The aqueous layer was extracted further with dichloromethane (20 ml). The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to provide the crude product which was purified by column chromatography (SiO2) eluting with a gradient of heptanes to 100% ethyl acetate to provide the title product as a white solid (79 mg, 9.7% yield). 1 H NMR (300 MHz, CDCl3) delta H NMR (300 MHz, (m, 1H), 8.79-8.57 (m, 1H), 8.50-8.23 (m, 1H), 8.02-7.83 (m, 2H), 7.84-7.72 (m, 1H), 5.56 (s, 2H).

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17228-38-5, A common heterocyclic compound, 17228-38-5, name is N-Methyl-1H-benzo[d]imidazol-2-amine, molecular formula is C8H9N3, 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 intermediate 2-XI (70mg, 0.173 mmol) in ACN (1.5 mL) and DMF (0.15 mL) was added A/-methyl-1 /-/-1 ,3-benzodiazol-2-amine (51 mg, 0.347 mmol) and Cs2C03 (282 mg, 0.867 mmol). The reaction mixture was heated in a sealed tube at 130C for 40 hours. On cooling, H20 (50 mL) and EtOAc (40 mL) were added. A solid appeared in the interphase, it was filtered and washed with EtOAc and Et20 to give final product 32 as a white solid (35 mg). LC-MS1 , tR= 3.98 min, MS: 515.2 [M+H]+ 1 H NMR (300 MHz, DMSO) delta 7.97 (d, J = 7.6 Hz, 1 H), 7.88 (q, J = 4.9 Hz, 1 H), 7.25 (d, J = 7.3 Hz, 1 H), 7.07 (t, J = 7.1 Hz, 1 H), 6.98 (t, J = 7.6 Hz, 1 H), 4.43 – 4.29 (m, 1 H), 4.24 (m, 1 H), 4.10 – 3.76 (m, 8H), 3.56 (m, 1 H), 3.46 – 3.36 (m, 2H), 3.03 (m, 1 H), 2.99 (d, J=4.9Hz, 3H), 2.94 (s, 3H), 2.89 (m, 1 H), 2.30 – 1.96 (m, 4H).

The synthetic route of 17228-38-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUNDACION CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS CARLOS III; PASTOR FERNANDEZ, Joaquin; FERNANDEZ-CAPETILLO RUIZ, Oscar; MARTINEZ GONZALEZ, Sonia; BLANCO APARICIO, Carmen; RICO FERREIRA, Maria del Rosario; TOLEDO LAZARO, Luis Ignacio; RODRIGUEZ ARISTEGUI, Sonsoles; MURGA COSTA, Matilde; VARELA BUSTO, Carmen; LOPEZ CONTRERAS, Andres Joaquin; RENNER, Oliver; NIETO SOLER, Maria; CEBRIAN MUNOZ, David Alvaro; WO2014/140644; (2014); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O2

0.76 g of imidazole-4-carboxylic acid methyl ester (6 mmol) was dissolved in 10 ml of acetone solution.0.66 ml (6.6 mmol) of 1,3-dibromopropane was added in that order.K2CO31.66g (12mmol),Bu4N+Br-0.12g (0.36mmol),Heated at 51 C for 7.5 h.TLC monitoring showed completion of the reaction. The reaction solution is dried,Dilute with 25 ml of ethyl acetate.Washed 5-6 times, the organic phase was washed with saturated sodium chloride (20 ml).Dry over anhydrous sodium sulfate, suction filtration, spin dry, flash column chromatography (PE/EA = 1:1),Methyl 1-(3-bromopropyl)imidazole-4-carboxylate (light yellow solid)0.57 mg, yield 38.9%.

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 17325-26-7.

Reference:
Patent; China Pharmaceutical University; Chen Li; Xu Manyi; Li Na; Pei Jianghong; Bao Na; Shi Wei; (31 pag.)CN109336944; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 1H-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 288-32-4, Recommanded Product: 288-32-4

General procedure: To a solution of Cu(OAc)2·H2O (0.01 mmol) in DMF (2 mL) were added aryl iodide (1.2 mmol), nitrogen-containing heterocycle (1.0 mmol), and Cs2CO3 (2 mmol) under nitrogen atmosphere. The mixture was stirred at 110 C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel.

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:
Article; Xu, Zhong-Lin; Li, Hong-Xi; Ren, Zhi-Gang; Du, Wei-Yuan; Xu, Wei-Chang; Lang, Jian-Ping; Tetrahedron; vol. 67; 29; (2011); p. 5282 – 5288;,
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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., name: 1H-Imidazole

Step 1 1H-Imidazole (10 g, 147 mmol) was dissolved in THF (150 mL). Dimethylsulfamoyl chloride (19 g, 132 mmol) was added followed by the dropwise addition of triethylamine (20 g, 198 mmol). The mixture was stirred at room temperature overnight. The mixture was poured into H2O (200 mL) and extracted with EtOAc three times. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give crude N,N-dimethyl-1H-imidazole-1-sulfonamide (27 g) that was used without further purification.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; US2009/62253; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem