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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 3034-50-2

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in ice water bath. After 10min,Add triethylamine (TEA) (278 mul, 2.0 mmol) to the reaction flask,The mixture was stirred in an ice-water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask.The reaction was moved to room temperature and reacted overnight. After the reaction was detected by TLC, the solvent was spin-dried.Alumina column chromatography (PE: EA = 2: 1) gave Intermediate 1b.

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; Xihua University; Wang Zhouyu; Qian Shan; Yang Lingling; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (23 pag.)CN110294714; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1964-77-8, 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. 1964-77-8, name is 5-Bromo-2-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To 5-bromo-2-methylbenzimidazole (38 g, 180 mmol) in TEtaF (400 mL) was added di-tert-butyl dicarbonate (39 g, 189 mmol). The reaction mixture was stirred at room temperature for 24 h and then concentrated. Ethyl acetate (400 mL) was added to the residue, and the solution was washed with 10% aqueous citric acid (2 x 100 mL), water (100 mL), and brine (100 mL), dried over sodium sulfate, and concentrated. Column chromatography on silica (gradient 20-30% ethyl acetate in hexane) provided 1,1 -dimethyl 6-bromo-2-methyl-lH- benzimidazole-1-carboxylate (27 g, 48% yield) as a beige solid. MS (EI) for Ci3Hi5BrN2O2: 312 (MH+)

The synthetic route of 5-Bromo-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; AAY, Naing; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen, E.; KIM, Angie, Inyoung; MANALO, Jean-claire, Limun; PACK, Michael; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WANG, Longcheng; WO2010/138490; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

930-62-1, name is 2,4-Dimethylimidazole, 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. Application In Synthesis of 2,4-Dimethylimidazole

PREPARATION 39 1-(3-Methyl-4-nitrophenyl)-2,4-dimethylimidazole STR118 A mixture of 5-fluoro-2-nitrotoluene (10.3 g), 2,4-dimethylimidazole (6.36 g) and sodium carbonate (7.5 g) was heated with stirring in dimethylformamide (40 cm3) at 130 for 40 hours. The cooled mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (2*25 cm3) to remove any neutral material. The combined aqueous phases were basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3*250 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was chromatographed on silica (Merck “MK 60.9385” [Trade Mark]) eluding with methanol:ethyl acetate, 1:19. Combination and evaporation of appropriate fractions afforded a solid (8.4 g) which was recrystallized from ethyl acetate to give 1-(3-methyl-4-nitrophenyl)-2,4-dimethylimidazole, m.p. 135.5-138. Analysis %: Found: C, 62.0; H, 5.7; N, 17.9; Calculated for C12 H13 N3 O2: C, 62.3; H, 5.7; N, 18.2.

The synthetic route of 930-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4728653; (1988); A;,
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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2,4-Dimethylimidazole

A. Sulfuric acid (30 ml, 0.56 mole) was added dropwise to 2,4-dimethylimidazole (10 g, 0.104 mole), and urea (6.24 g, 0.104 mole), in a 1 l. flask cooled in ice. This was followed by the addition of fuming nitric acid (30 ml, 0.72 mole). When all had been added, the flask was heated at 200 C. for 1-2 minutes, whereupon a vigorous reaction ensued, necessitating the removal of the heat. When the reaction subsided, heating is continued for 10 minutes. The flask was then allowed to cool, and the reaction mixture was added to 300 ml of H2 O. The solution was adjusted to pH 5 with aqueous sodium hydroxide (about 40 g of sodium hydroxide was required). The resulting precipitate was filtered off and dried in vacuum to give 9.9 g of 2,4-dimethyl-5-nitroimidazole.

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 930-62-1.

Reference:
Patent; Merck & Co., Inc.; US4678799; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, 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. category: imidazoles-derivatives

(b) 5-Bromo-lH-imidazole[00356] 2,4,5-Tribromo-lH-imidazole (32 g , 0.105 mol) was refluxed with 20% aqueous sodium sulphite solution (66.34 g, 0.527 mol) for 8 h. The solid product precipitated upon cooling and was collected by vacuum filtration to yield 12.5 g of the desired product. LC-MS: 147, 149 (M+H+).

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emerson; HEWITT, Michael, Charles; JONES, Philip; XIE, Linghong; WO2011/150156; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, 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 89830-98-8 as follows.

J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0¡ãC under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0¡ãC. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H).

According to the analysis of related databases, 89830-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; BONFANTI, Jean-Francois; DOUBLET, Frederic Marc Maurice; EMBRECHTS, Werner; FORTIN, Jerome Michel Claude; MC GOWAN, David Craig; MULLER, Philippe; RABOISSON, Pierre Jean-Marie Bernard; WO2013/68438; (2013); 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 360-97-4 as follows. Application In Synthesis of 4-Amino-1H-imidazole-5-carboxamide

EXAMPLE 3 Preparation of 1-(m-cyanobenzyl)-5-aminoimidazole-4-carboxamide A mixture of 5-aminoimidazole-4-carboxamide (5.00 g), potassium carbonate (12.0 g), and alpha-bromo-m-tolunitrile (9.80 g) were refluxed in acetone (300 ml) for 24 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and filtered. The solid residue was washed with acetone and the combined filtrates were evaporated to dryness. The residual solid was dissolved in acetone (50 ml), concentrated to a volume of 20 ml in vacuo, and diluted with diethyl ether (100 ml) to provide a gum. The solvent was decanted from the residue and deposited crystals of crude product on standing. The gum was triturated twice with acetone, and the acetone layers were combined with the above crystals, and evaporated to provide 5.9 g of a dark gum. The gum was dissolved in methanol (100 ml), filtered, added to 100 ml. E. Merck 7734 silica gel, and evaporated to dryness in vacuo. The product on silica gel was placed on top of a column of 1200 ml E. Merck 7734 silica gel and eluted with 9:1 v/v methylene chloride/methanol. After a forerun of 1.0 l, 400 ml fractions were collected and fractions 8-11 and 12-15 were combined separately and evaporated to dryness. The solid product from fractions 8-11 was triturated with a small volume of acetone and filtered. The filtrate was combined separately with the product from fractions 12-15 and evaporated to dryness. The product was recrystallized from methanol to provide 320 mg of 1-(m-cyanobenzyl)-5-aminoimidazole-4-carboxamide, m.p. 246-247 C.

According to the analysis of related databases, 360-97-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4659720; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 25676-75-9, name is 4-Bromo-1-methylimidazole, 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. category: imidazoles-derivatives

To a solution of compound 82-1 (0.04 g, 0.10 mmol, 1.0 eq) and compound 82-2 (1104) (16.3 mg, 0.10 mmol, 1.0 eq) in dioxane (5.0 mL) was added H20 (0.5 mL) Pd(dppf)Cl2 (7.4 mg, 10.14 umol, 0.1 eq) and Na2C03 (21.5 mg, 0.20 mmol, 2.0 eq). The mixture was stirred at 80 C for 16 hour under N2 atmosphere. LCMS showed desired compound was found. The reaction was filtered through Celite and concentrated under reduced pressure to give a residue. The crude product was purified by prep-HPLC to give Compound 82 (6.64 mg, 18.86 umol, 18.60% yield). LCMS (ESI): RT = 0.634 min, mass calc. for Ci7H24N402S 348.16, m/z found 348.9 [M+H]+; 1HNMR (400 MHz, CDC13) delta 8.55 (s, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.54 (dd, J = 2.3, 8.8 Hz, 1H), 7.47 (s, 1H), 7.24 (s, 1H), 6.69 (d, J = 9.0 Hz, 1H), 4.24 (q, J= 5.4 Hz, 1H), 3.75 (s, 3H), 3.44 (s, 1H), 2.62 (d, J = 5.5 Hz, 3H), 2.12 – 2.00 (m, 2H), 1.86 – 1.75 (m, 2H), 1.69 – 1.64 (m, 1H), 1.48 – 1.25 (m, 5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25676-75-9, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); 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, Product Details of 28890-99-5

250ml four bottles,In the atmosphere of nitrogen gas,0.01 mol of 5H-benzimidazol [1,2-a] benzimidazole was added,0.015 mol of raw material C,0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,250ml toluene,Heated to reflux for 24 hours,Sampling point plate, the reaction is complete, natural cooling, filtration, the filtrate steamed, silica gel column, the target product, purity 95.26, yield 19.70%.

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; Jiangsu Sanyue Photoelectric Technology Co., Ltd.; Wang, Lichun; Li, Chong; Xu, Kai; Zhang, Zhaochao; Ye, Zhonghua; (39 pag.)CN106467552; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 25 mL flask with a magnetic stirring bar was charged with CuI(9.6 mg, 0.05 mmol), metformin (0.1 mmol), Cs2CO3 (652 mg,2.0 mmol), imidazole (1.0 mmol), an aryl halide (1.1 mmol), andDMF (5 mL). The mixture was stirred for 10 min at room temperature,and then heated to 110?C for the appropriate amount of time(see Table 2). The progress of the reaction was monitored by TLC.After completion of the reaction, the mixture was extracted with EtOAc (5 1 mL) and the organic phase separated and evaporated. Further purification by column chromatography gave the desired coupled product.

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

Reference:
Article; Ghorbani-Vaghei, Ramin; Hemmati, Saba; Veisi, Hojat; Tetrahedron Letters; vol. 54; 52; (2013); p. 7095 – 7099;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem