Imidazoles-derivatives

6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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.

General procedure: To a stirred solution ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

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 6775-40-2.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

104619-51-4,Some common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, molecular formula is C7H7N5, 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.

Di(imidazole-1-yl)methanimine (17.59 mmol, 2.83 g) was added to a solution of 2-amino-6-chlorophenol (7.03 mmol, 1.01 g) in acetonitrile (40 mL) with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for ten hours. The reaction was then concentrated under reduced pressure and silica gel column chromatography (2:1 hexanes/ethyl acetate) provided a crystalline white solid in a 92% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Di(1H-imidazol-1-yl)methanimine, its application will become more common.

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 33016-47-6

[1816] To a stirred solution of starting material benzyl amine (0.99 g, 8.87 mmol) in MeOH (50 mL) under nitrogen inlet at room temperature, was added sodium acetate (0.73 g, 8.87 mmol), 3A molecular sieves (3.0 g) and aldehyde (3.0 g, 8.87 mmol). The resulting solution was stirred at room temperature overnight, followed by addition of NaBH4 (0.67 g, 17.74 mmol), then stirred for 4 hrs and concentrated to dryness, followed by extraction with CH2Cl2-1N NaOH. The combined organic layer was dried over MgSO4, filtered, concentrated to dryness and purified by column chromatography on silica gel, eluting with 2%MeOH-NH3/98%CH2Cl2 to give light yellow oil (3.75 g, 98% yield, MH+=430.2)

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, 33016-47-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhu, Hugh Y.; Njoroge, F. George; Cooper, Alan B.; Guzi, Timothy; Rane, Dinanath F.; Minor, Keith P.; Doll, Ronald J.; Girijavallabhan, Viyyoor M.; Santhanam, Bama; Pinto, Patrick A.; Vibulbhan, Bancha; Keertikar, Kartik M.; Alvarez, Carmen S.; Baldwin, John J.; Li, Ge; Huang, Chia-Yu; James, Ray A.; Bishop, W. Robert; Wang, James J-S; Desai, Jagdish A.; US2003/229099; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 152628-02-9, 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.

10 g (0.0329 mol) of 2-propyl-4-methyl-6-(r-methylbenzimidazole-2- yl)benzimidazole (1) was dissolved in 60 ml of dimethylsulfoxide (DMSO). 3.7 g (0.0329 mol) of Potassium tert-butoxide was added to the aforementioned solution and stirred at room temperature (25-3O0C) for 30 min. Afterwards, 11.45 g (0.0329 mol) of tert-Butyl-4-bromomethylbiphenyl-2-carboxylate (2) was added and the obtained mixture was stirred at room temperature (25-3O0C) for 3 h. At this stage, the reaction was quenched with water (400 ml) and stirred for 30 min. The reaction mass was filtered. The resulting wet cake was slurried in water (200 ml) and stirred for 30 min. The reaction mass was filtered and the obtained solid was dried under vacuum at 60-650C until constant weight. 18.3 g obtained (93% HPLC).

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Patent; INKE, S.A.; SINGH, Santosh; JOSHI, Anil; NEWADKAR, Ravindranath; WO2010/149565; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-50-2, The chemical industry reduces the impact on the environment during synthesis 3034-50-2, name is Imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

Intermediate 18:l-trityl-lH-imidazole-4-carbaldehyde[00417 ] Triethylamine (3.05 ml, 21.86 mmol) was added to a solution of lH-imidazole-4- carbaldehyde (2 g, 20.82 mmol) and triphenylmethyl chloride (5.80 g, 20.82 mmol) in N5N- dimethylformamide (20 ml). The reaction mixture was stirred at room temperature for 18 hours. The crude mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The organic phase was washed dried over sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallised from dichloromethane and hexanes to afford the title compound as a cream solid (4.7 g, 67% yield).[00418] 1H NMR (DMSO-d6, 400 MHz) delta 7.10-7.16 (6H, m), 7.36-7.57 (9H, m), 7.63 (IH, s), 7.64 (IH, s), 9.91 (IH, s).

The chemical industry reduces the impact on the environment during synthesis Imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2008/94992; (2008); A2;,
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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 2849-93-6

General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3242 – 3253;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-49-1, 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. 872-49-1, name is 5-Chloro-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-1-methyl-imidazole (4.0 g, 34.32 mmol) was dissolved in a mixture of 4.0 g of conc. nitric acid and 14 mL of water, and concentrated in vacuo to give a yellow slurry. To this mixture was added dropwise 12 g of conc. sulfuric acid and heated to 95C for 2 hours. Upon cooling, ice was added to the reaction mixture, which was then left standing 10 hours at 5C. The white precipitation was collected by filtration, washed with water, recrystallized from ethanol and dried in vacuo to give compound 60A.

The synthetic route of 5-Chloro-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; EP1066286; (2009); B1;,
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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows., 288-32-4

General procedure: Imidazole (3)/benzimidazole(5) (10 mmol) was dissolved in 10 ml of DMSO and solid NaOH(15 mmol) was then added it. The resulting pale yellow suspensionwas stirred in air at room temperature for 1.5 h, after which, thealkyl bromides or benzyl chlorides (15 mmol) were added andallowed to react until completion (TLC). Water (50 ml) was thenadded and the products were extracted with ethyl acetate. Combinedorganic layers were washed several times with water, thenwith brine, dried over Na2SO4 and subjected to chromatographicpurification over silica (100-200 mesh) using MeOH: EtOAc 5:95(v/v) as the mobile phase. Compounds 4a-f were isolated as yellowoils whereas, the compounds 7a-e were white solid. Spectroscopic data of the N-alkyl imidazoles are in accord with earlier literatureand thus are not shown here [30].

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; Chatterjee, Tanmay; Kumar, N. Tanmaya; Das, Samar K.; Polyhedron; vol. 127; (2017); p. 68 – 83;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Name is 2-(1H-Imidazol-1-yl)ethanol, 1615-14-1, 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.

Synthesis of benzyl (25,4a5,6a5,6bR,8a5, lOS, 12a5, l2bR, l4bR)-10-((2-(2-(1H-Imidazol-1-yl)ethoxy)-2-oxoethyl)carbamoyl)-2,4a,6a,6b,9,9, 1 2a-heptamethyl- 13 -oxo- 1,2,3 ,4,4a, 5,6,6a,6b,7, 8,8a,9, 10,11,12,1 2a, 1 2b, 13,1 4b-icosahydropicene-2-carboxylate (44-1). Into a 1 00-mL roundbottom flask, was placed EDCI (53.4 mg, 0.28 mmol, 1.50 equiv.), DCM (15 mL), DMAP (113 mg, 0.92 mmol, 5.00 equiv.). The resulting solution was stirred for 1 h at room temperature. 30- 2 (120 mg, 0.19 mmol, 1.00 equiv.) was added. The resulting solution was allowed to react, withstirring, for an additional 1 h at 55 C. 2-(1H-imidazol-1-yl)ethan-1-ol (83 mg, 0.74 mmol, 4.00 equiv.) was added. The resulting solution was allowed to react, with stirring, for an additional overnight at 55 C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (9:1). This resulted in 85 mg (62%) of 44-1 as an off-white solid.

Statistics shows that 2-(1H-Imidazol-1-yl)ethanol is playing an increasingly important role. we look forward to future research findings about 1615-14-1.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-67-6, 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. 33468-67-6 name is 2-Methyl-4-(trifluoromethyl)-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.

Compound 16.3. 2-Methyl-lH-imidazole-4-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution of 2 -methyl-4-(trifluoromethyl)-lH- imidazole (compound 16.2, 300 mg, 2.00 mmol) in 5% ammonium hydroxide (35 mL). The resulting solution was stirred for 4 days at room temperature, then the pH of the solution was adjusted to 7 with acetic acid. The aqueous phase was extracted with of ethyl acetate (3 x 10 mL) and the combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure to yield 170 mg (79%) of the title compound as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-4-(trifluoromethyl)-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem