Month: February 2021

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;,
Imidazole – Wikipedia,
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

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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H8N2O

COMPOUND 12.1. 10: N,N-DIETHYL-4-{6-METHOXY-2-[(2-PHENYL-1H- IMIDAZOL-5-YL) METHYL1-1, 2, 3, 4-TETRAHYDROISOQUINOLIN-1- YUBENZAMIDE; INTERMEDIATE 5.1. 7 (15 mg, 0.04 mmol) and 2-phenyl-4 (5)- imidazolecarbaldehyde (20 mg, 0.12 mmol) were dissolved in DCE (2 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (34 mg, 0.16 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman 1PS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (80 mg, 0.016 mmol, 77%). 1H NMR (500 MHz, CDCl3) : 1.05, 1.15 (2 brs, 6H), 3.10-3. 35 (m, 4H), 3.40-3. 65 (m, 4H), 3.68 (s, 3H), 3.82 (m, 2H), 5.82 (s, 1H), 6.55-6. 82 (m, 4H), 7.30-7. 77 (m, 6H), 7.98 (d, J 9 Hz, 1H), 8. 32 (d, J 2.5 Hz, 2H). (+) LRESIMS m/z 493 [M+H]+.

The synthetic route of 68282-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4238-71-5, 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. 4238-71-5, name is 1-Benzyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cold (-50 0C) suspension of 1 -benzyl -IH- imidazole (1.58 g, 10.0 ramol) in anhydrous diethyl ether (50 mL) under nitrogen was added ?-butyl lithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) dropwise. After being stirred for 20 min at -50 0C, dry carbon dioxide (passed through Drierite) was bubbled into the reaction mixture for 10 min before it was allowed to warm up to 25 0C. The heavy precipitate which formed on addition of carbon dioxide to the reaction mixture was filtered to yield a hygroscopic, white solid which was taken up in water (7 mL) , acidified to pH = 3, cooled, and induced to crystallize with scratching. Filtration of the precipitate gave a white solid which was suspended in methanol, treated with IN HCl/diethyl ether (4 mL) and concentrated in vacuo. Lyophilization of the residue from water (5 mL) afforded Cap-136 as a white solid (817 mg, 40%) . 1H NMR (300 MHz, DMSO~d6) 6 7.94 (d, J = 1.5 Hz, IH), 7.71 (d, J = 1.5 Hz, IH) , 7.50-7.31 (m, 5H),5.77 (s, 2H} ; Rt = 0.51 min (Cond. -MS-W5) ; 95% homogenity index; LRMS: Anal. CaIc. for [M+H] + CnH12N2O2: 203.08; found: 203.11.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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, Recommanded Product: Ethyl 1H-imidazole-2-carboxylate

To a solution of ethyl 1H-imidazole-2-carboxylate (500 mg, 3.57 mmol) in DMF (10 mL) were added tert-butyl (2-bromoethyl)carbamate (800 mg, 3.57 mmol) and K2CO3 (986 mg, 7.14 mmol), and the resulting white suspension was stirred at 60 C. for 16 h, allowed to cool to RT, then concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (20% to 100% EtOAc in hexanes) to give the title compound as a white solid (751 mg, 74%). MS (ES+) C13H21N3O4 requires: 283, found: 284 [M+H]+.

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem