Imidazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, 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 33543-78-1, SDS of cas: 33543-78-1

PREPARATION 32 1H-imidazole-2-carboxylic acid 21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL). The reaction mixture was warmed up to reflux, and stirred for 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum. The crude residue (3.0 g) was used in next step without further purification. LRMS (m/z): 113 (M+1)+.

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; Almirall, S.A.; EP2518070; (2012); 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. 29914-81-6, name is 1,3-Bis(1H-benzo[d]imidazol-2-yl)benzene, A new synthetic method of this compound is introduced below., Formula: C20H14N4

General procedure: To 10 mL dry acetone were added [Ru(H2bip)Cl3] (54 mg,0.10 mmol) and AgOTf (96 mg, 0.37 mmol). The mixture wasrefluxed for 2 h before cooling to room temperature. The resultingAgCl precipitate was removed by filtration, and the filtrate wasconcentrated to dryness. To the residue were added ligand Mebib(36.9 mg, 0.11 mmol), DMF (10 mL), and t-BuOH (10 mL). Themixture was then refluxed for 24 h. After cooling to room temperature,the solventwas removed under reduced pressure, and theresiduewas dissolved in a mixture of 10 mL methanol and 1mL 1Maq. HCl. The mixture was then treated with 100 mg KPF6. Theresulting precipitate was collected by filtration and washing withwater and Et2O. The obtained solid was subjected to flash columnchromatography on silica gel (eluent: CH3CN/H2O/aq.KNO3, 100/10/0.2) to give 34.5 mg of 1(PF6)2 in 37% yield.

The synthetic route of 29914-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Jiang-Yang; Zhong, Yu-Wu; Journal of Organometallic Chemistry; vol. 845; (2017); p. 144 – 150;,
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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H8N2O

To a 0¡ãC solution of 1 -methyl- lH-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3 x 50 mL) and CH2Cl2 (1 x 50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1 -methyl- lH-benzimidazol-2-yl)methanol was obtained (1.1 g, 99percent yield). The product was used without further purification.

The synthetic route of 3012-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHLORION PHARMA, INC.; UNIVERSITE LAVAL; ATTARDO, Giorgio; TRIPATHY, Sasmita; WO2010/132999; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17325-26-7, 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. 17325-26-7 name is Methyl 1H-imidazole-5-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 mixture of 4-(bromomethyl)- 1,2-difluorobenzene (10.0 g, 48.3 mmol), 1H-imidazole-4-carboxylate (12.2 g, 96.6 mmol) and potassium hydroxide (5.4 g, 96.6 mmol) in tetrahydrofuran (100 mL) was heated at 70 C for 12H. After cooled, the mixture was filtered and the filtrate was concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 100%) ethyl acetate in petroleum ether) to afford methyl 1-(3,4-difluorobenzyl)-1H-imidazole-4-carboxylate (5.0 g, 41% yield) as a white solid: LCMS (5 to 95% acetonitrile in water + 0.03% trifluoroacetic acid over 1.5 mins) retention time 0.70 min, ESI+ found [M+H] = 252.8.

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

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 760212-58-6,Some common heterocyclic compound, 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, molecular formula is C19H13BrN2, 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.

In one 250 mL flask, 2.4 g (5.00 mmol) of Int.16, 1.9 g (5.50 mmol) of intermediate (13) 0.06 g (0.50 mmol) of Pd(PPh3)4, 0.7 g (12.5 mmol) of K2CO3, 50 mL of toluene, 25 mL of EtOH and 25 mL of H2O were mixed and then refluxed. After the reaction is complete, cool to room temperature and add 200 mL H2O. The mixture was extracted twice with 300 mL of dichloromethane (DCM), the extract was dried with Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The solid was dissolved in chloroform and purified by silica gel column chromatography (dichloromethane (DCM) / ethyl acetate (EA)). Solidification with dichloromethane (DCM) / n-hex and filtration gave 1.3 g (yield: 43.3%) of compound 4-418 (WS16-30-067) as a beige solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Raepto Co., Ltd.; Kim Gyu-ri; Go Byeong-su; Kim Hye-jeong; Ryu Yong-jae; Im Cheol-su; Park Yong-pil; Yoon Jeong-hun; Han Gap-jong; Oh Yu-jin; (85 pag.)KR2017/142950; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-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 693-98-1, COA of Formula: C4H6N2

General procedure: To a solution of 1 (0.02 mmol) in H2O/MeCN (v/v=2/1, 4 mL) was added 1H-imidazole (1.0 mmol) and arylboronic acid (2 mmol)under O2 atmosphere. The mixture was stirred at 60 ¡ãC for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and CH2Cl2. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. 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.

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:
Article; Xue, Jiang-Yan; Li, Jun-Chi; Li, Hong-Xi; Li, Hai-Yan; Lang, Jian-Ping; Tetrahedron; vol. 72; 44; (2016); p. 7014 – 7020;,
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. 53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, A new synthetic method of this compound is introduced below., Product Details of 53484-15-4

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-(tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoic acid (2.35 g, 9.47 mmol, 1.00 equiv) in CH3CN/toluene (70/12 mL), 5-bromo- l-methyl- lH- benzo[d] imidazole (2 g, 9.48 mmol, 1.00 equiv), Pd(PPh3)4 (548 mg, 0.47 mmol, 0.05 equiv), sodium carbonate (0.4M, 50 mL, 2.00 equiv). The resulting solution was stirred for 18 h at 90C. After cooled to room temperature, the reaction mixture was poured into 50 ml of water. The mixture was washed with 2×100 mL of ethyl acetate and the aqueous layer was collected. The pH value of the solution was adjusted to 4 with hydrochloric acid (IN). The solids were collected by filtration and dried under vacuum. This resulted in 2 g (84%) of the title compound as a white solid, which was dried under vacuum. LC- MS (ES, m/z): 253 [M+H]+

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; FORMA THERAPEUTICS, INC.; BAIR, Kenneth, W.; LANCIA, David, R.; LI, Hongbin; LOCH, James; LU, Wei; MARTIN, Matthew, W.; MILLAN, David, S.; SCHILLER, Shawn, E.r.; TEBBE, Mark, J.; WO2014/164749; (2014); 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. 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C8H14N2

1.86 g (5 mmol) of dysprosium oxide was dissolved in about 51 mmol of a 25% by volume aqueous solution of nitric acid,Stirring until completely dissolved,Further, 2.76 g (20 mmol) of 1-butyl-2-methylimidazole,60 reaction conditions 18h,The solvent was evaporated,To give 7.50 g of a light yellow transparent liquid 1-butyl-2-methylimidazole penta nitryloidate ion liquid.

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; Sichuan University; Tao, Guohong; Tang, Ning; He, Ling; (16 pag.)CN106146541; (2016); 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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9ClN2

General procedure: To a 25mL flask was added 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (0.46 g, 2mmol), 4-(2-chloroethyl)morpholine (0.30 g, 2mmol), potassiumcarbonate (0.42 g, 3mmol) and DMF (8 mL), the reaction mixturewas heated at 60 C and stirred for 6 h. After the reaction was completed,the DMF was removed at reduced pressure and the residue was purified onsilica gel with chloroform/methanol (V:V 100:1) to give the title compoundas awhite powder. Yield 94.1%, m.p. 80-82 C. 1H NMR (600MHz,DMSO-d6) delta 7.51 (d, J=2.2 Hz, 1H, Ar-H), 7.17 (dd, J=8.5, 2.2Hz, 1H,Ar-H), 6.97 (d, J=8.5 Hz, 1H, Ar-H), 4.65 (s, 2H, Ar-H), 4.02 (t,J=6.4Hz, 2H, CH2), 3.53 (s, 4H, CH2¡Á2), 2.47 (t, J=6.4 Hz, 2H, CH2),2.43 (s, 4H, CH2¡Á2). ESI-MS: m/z 341.0 [M+H]+.Compounds 2b-j were synthesized according to the procedure describedin 2a.

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 53710-78-4.

Reference:
Article; Dong, Fu-Dan; Liu, Dan-Dan; Deng, Cheng-Long; Qin, Xiao-chun; Chen, Kai; Wang, Jian; Song, Hong-Rui; Ding, Huai-Wei; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3982 – 3991;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 86718-07-2,Some common heterocyclic compound, 86718-07-2, name is Ethyl 4-(1-Imidazolyl)benzoate, molecular formula is C12H12N2O2, 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 2 N-(4-Methoxy-3-(4-methyl-1-piperazinyl)phenyl)-4-(imidazol-1-yl) benzamide Ethyl 4-(imidazol-1-yl)benzoate (0.5 g, 2.3 mmol) was heated at reflux in 5N HCl (40 ml) for 1 h, evaporated to dryness under reduced pressure and the resulting white solid dried in vacuo to afford 4-(imidazol-1-yl)benzoic acid This was suspended in dry toluene (40 ml) and thionyl chloride (2 ml) added under argon. The mixture was heated to reflux for 1.5 h and then evaporated to dryness under reduced pressure. The oil was dissolved in dichloromethane under argon and 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (551 mg, 2.3 mmol) was added followed by triethylamine (2 ml). The mixture was stirred at room temperature under argon for 2 h and then partitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml), and the organic extracts dried (sodium sulphate). The organic solution was filtered, evaporated to dryness under reduced pressure and purified by column chromatography (silica, chloroform/methanol 5-10%) to afford the amide (809 mg, 90%) which was crystallized from methanol diethyl ether as the oxalate salt. 1H NMR (CDCl3) (free base) delta: 2.38 (3H, s), 2.66 (4H, bm), 3.15 (4H, bm), 3.90 (3H, s), 6.87 (1H, d), 7.29 (2H, m), 7.37 (1H, s), 7.52 (2H, d), 7.86 (1H, s), 7.93 1H, s), 8.01 (2H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-Imidazolyl)benzoate, its application will become more common.

Reference:
Patent; SmithKline Beecham p.l.c.; US5834471; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem