Month: January 2021

4887-83-6, name is 7-Methyl-1H-benzo[d]imidazole, 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: 4887-83-6

4-Methyl-1 H-benzimidazole (328 mg; APAC) was dissolved in DCM (7 ml_), di-te/f-butyl dicarbonate (0.634 ml.) was added and the solution was stirred at RT for 18 hr. The solvent was evaporated to give the title compound (575 mg) as a yellow oil. It was used without further purification, m/z [M+H]+: 233.2. Retention time 1.18 min (LC/MS method 3

The synthetic route of 4887-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

The ethyl 1-(4-chloro-1-oxo-2-indanyl)-imidazole-2-carboxylate can be prepared as in Example 1 for the preparation of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate but starting with 2.8 g of ethyl imidazole-2-carboxylate, 0.6 g of 80percent sodium hydride, 6.4 g of 2-bromo-4-chloro-1-indanone and a total of 80 ml of anhydrous dimethylformamide. After silica gel chromatography with a dichloromethane-ethyl acetate mixture (80-20 by volume), 1.85 g of ethyl 1-(4-chloro-1-oxo-2-indanyl)imidazole-2-carboxylate are obtained Rf=0.3, thin-layer chromatography on silica gel; solvent: dichloromethane-ethyl acetate (80-20 by[volume)]. The 2-bromo-4-chloro-1-indanone can be prepared in the following manner:

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

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5677306; (1997); A;,
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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1H-Imidazole-4,5-dicarboxylic acid

Into a 100mL round bottom flask, successively added the 1-hydimidazole-4, 5-dicarboxylic acid (600 mg, 1eq, 3.84mmol), thionyl chloride (1.81mL, 6.5eq, 24.8mmol), ultra-dry dimethylformamide (DMF) (0.15mL, 0.5eq, 1.92mmol) and 5mL of toluene, refluxed at 90 C for 16 h. After the reaction, cooling, by using too much toluene in the reaction solution with straw, dissolved in thionyl chloride and DMF aspiration, toluene washed twice and then obtained crude product (compound 1), without further purification directly use for the next step.

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-87-0

Methyl (1-N-methyl)imidazole-4-carboxylate. A mixture of 4-iodo-1-methyl-1H-imidazole (500 mg, 2.40 mmol), trans-dichlorobis(triphenylphosphine)palladium(II) (255 mg, 0.30 mmol) and triethylamine (3 mL) in methanol (30 mL) in a pressure vessel was purged with argon for 10 min. The vessel was then pressurized with carbon monoxide to 250 psi and heated at 100 C. for 2 days. After cooling to room temperature, the reaction mixture was filtered through Celite, and concentrated under vacuum. The resultant residue was purified by flash chromatograph on silica gel (5% MeOH in CHCl3) to give title compound. 1H NMR (400 MHz, CDCl3) delta 7.60 (s, 1H), 7.28 (s, 1H), 3.90 (s, 3H), 3.78 (s, 3H).

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; Payne, Linda S.; Tran, Lekhanh O.; Zhuang, Linghang H.; Young, Steven D.; Egbertson, Melissa S.; Wai, John S.; Embrey, Mark W.; Fisher, Thorsten E.; Guare, James P.; Langford, H. Marie; Melamed, Jeffrey Y.; Clark, David L.; US2003/229079; (2003); 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. 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H6N2O2

HOBt (3.7 g) and WSC (4.6 g) were successively added to a suspension of 2-methylimidazole-4-carboxylic acid (2.0 g) in acetonitrile (150 mL), and the mixture was stirred at room temperature for 20 minutes. To this reaction solution was added a solution of tert-butyl 4-[(2-hydroxyethyl)amino]piperidine-1-carboxylate (4.7 g) obtained in Example 38a) and triethylamine (8.0 mL) in acetonitrile (50 mL), and the mixture was stirred at room temperature for 15 hours. After acetonitrile was distilled off under reduced pressure, chloroform (100 mL) and water (100 mL) were added to the residue. An organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with a basic silica gel column (ethyl acetate: ethanol = 5:1) to obtain the title compound (1.0 g, 18%) as a colorless oil. NMR (200 MHz, CDCl3) delta: 1.47 (9H, s), 1.84 (4H, bs), 2.37 (2H, bs), 2.78 (2H, bs), 3.82 (4H, bs), 4.27 (3H, bs), 7.31 (1H, bs).

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 1457-58-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1564213; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Safety of 1H-Imidazole

General procedure: Iodobenzene (1.0 mmol), imidazole (1.5 mmol), TEPA (2.0 mmol), TBAB (0.3 mmol), CuI (0.1 mmol), and 3 mL H2O were added to a 10 mL flask, which was subsequently capped with a rubber balloon. The mixture was stirred in a preheated oil bath at 125 C for 12 h. After cooling the mixture to the room temperature, 5 mL water was added and the product was extracted by ethyl acetate (10 mL¡Á3). The combined organic layer was washed by brine (15 mL), dried over anhydrous MgSO4, and evaporated under the reduced pressure. Further purification by silica gel column chromatography (6:1 petroleum ether/ethyl acetate) give the 1-phenyl-1H-imidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-32-4, its application will become more common.

Reference:
Article; Yang, Qichao; Wang, Yufang; Yang, Li; Zhang, Mingjie; Tetrahedron; vol. 69; 30; (2013); p. 6230 – 6233;,
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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), A new synthetic method of this compound is introduced below., Formula: C6H12N6O4S

EXAMPLE 2 5-(4-Pyridyl)imidazo[1,2-a]pyrimidine A mixture of 5.29 g of 2-aminoimidazole hemisulfate, 3.28 g of anhydrous sodium acetate and 7.04 g of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one (prepared according to the procedure of Example 63 in U.S. Pat. No. 4,281,000) in 100 ml of glacial acetic acid was heated under reflux for 16 hours. The procedure of the above Example 1 was followed and the title compound was obtained as pale yellow needles, mp 244-245 C.

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; American Cyanamid Company; US4551530; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1, 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. 33543-78-1 name is Ethyl 1H-imidazole-2-carboxylate, 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.

A solution of the required amine (0.20 mmol; 2 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is quenched by the addition of a sat. aq. KH2P04 solution and the reaction mixture is stirred at rt for 20 h. The reaction mixture is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and ethyl imidazole-2-carboxylate and proceeding in analogy to Procedure AQ, the title compound was obtained, after purification by prep-HPLC (basic conditions), as an amorphous solid (22percent yield).MS (ESI, m/z): 340.10 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 305790-48-1, name is 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, 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 305790-48-1, Recommanded Product: 305790-48-1

A mixture of 6-bromo-l-methyl-l,3-dihydro-2H-benzo[d]imidazol-2-one (10.0 g, 44.2 mmol), l, -Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (3.6 g, 4.42 mmol), TEA (9.0 g, 88.5 mmol) in MeOH (200 mL) and DMF (10 mL) was sparged with carbon monoxide for about 10 min, placed under 4 atm carbon monoxide atmosphere, and heated to 130 C for 17 hours. The reaction mixture was cooled down to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE: EA = 2: 1 ) to give product (7.0 g, 76.9%) as a yellow solid. NMR (400 MHz, DMSO-d6) S 1 1.27 (s, 1 H), 7.77 – 7.53 (m, 2 H), 7.07 (d, J = 8.1 Hz, 1 H), 3.84 (s, 3 H), 3.33 (s, 3 H); LC/MS (ESI, m/z): [M +1]+ = 207.1.

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, 6-Bromo-1-methyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; MAINOLFI, Nello; JI, Nan; ZHANG, Yi; WEISS, Matthew M.; (223 pag.)WO2019/60693; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4238-71-5, name is 1-Benzyl-1H-imidazole, molecular formula is C10H10N2, 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. Computed Properties of C10H10N2

1 mol of the compound III obtained in the step (1)1 mol of benzyl chloride was dissolved in THF (tetrahydrofuran)Heated to reflux 12h,The above solution was spin-dry with a rotary evaporator,Then using 3: 1 CH 2 Cl 2 and CH 3 OH as the eluent for chromatographic separation,Obtained pale yellow oily liquid, which is Compound II;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4238-71-5, its application will become more common.

Reference:
Patent; Jiangsu Atomic Medical Institute; Lin Jianguo; Lv Gaochao; Qiu Ling; Guo Liubin; Yang Hui; Wang Tengfei; (17 pag.)CN104650155; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem