Category: imidazoles-derivatives

Reference of 6478-79-1, 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 6478-79-1 as follows.

To a solution of compound 1 (0.010?mol) in dry acetone, K2CO3 (0.025?mol) was added and the mixture was stirred at room temperature for 20?min. Then, methyl bromoacetate (0.011?mol) was added to the mixture and stirred at room temperature for one night. Afterwards, the reaction was completed (monitored by TLC, ethylacetate/hexane, 3:1). The product was precipitated by addition of water. It was filtrated off, and recrystallized from ethanol/water, 1:2. Yield: 92%, mp: 166-167?C. 1H NMR (DMSO-d6) ppm: 1.20 (3H, t, J?=?6.8?Hz, CH3), 2.44 (3H, s, CH3), 4.17 (2H. q, J?=?6.8?Hz, OCH2), 5.20 (2H, s, N-CH2), 7.78 (1H, s, Ar-H), 7.91 (1H, s, Ar-H). 13C NMR (DMSO-d6) ppm: 13.78, 14.42 (CH3), 45.12 (NCH2), 61.90 (OCH3), ArC:[112.25, 119.83, 124.45, 124.64, 135.65, 142.19], 155.72 (C=N), 168.35 (C=O). Anal. calcd. (%) for C12H12Cl2N2O2: C, 50.20; H, 4.21; N, 9.76. Found: C, 50.28; H, 4.26; N, 9.69.

According to the analysis of related databases, 6478-79-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mente?e, Emre; Emirik, Mustafa; Soekmen, Bahar Bilgin; Bioorganic Chemistry; vol. 86; (2019); p. 151 – 158;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-nitro-5-(phenylamino)phenol (KR-100061) (12.03 mmol, 2.77 g) in methanol (120 mL), PtO2 (0.60 mmol, 0.14 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (45 mL). The filtrate was concentrated in vacuo yielding an intense purple residue. The residue was quickly re-dissolved in acetonitrile (60 mL) and di(imidazole-1-yl)methanimine (30.08 mmol, 4.85 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (3:1 hexanes/ethyl acetate) provided a crystalline white solid in a 69% yield. The product of the reduction (2-amino-5-(phenylamino)phenol) is air unstable and appropriate measures should be taken to minimize air exposure.

The synthetic route of Di(1H-imidazol-1-yl)methanimine has been constantly updated, and we look forward to future research findings.

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

3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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. Formula: C14H19N3O2

Example-1 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III) Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 40.0 g, 0.153 mol) was added to 2-bromoethanol (80 mL) and agitated for 15-30 minutes. Acetonitrile (80 mL) and calcium carbonate (61.3 g, 0.61 mol) were added to the reaction mixture. The reaction mixture was heated to 80-90 C. within 2 hours and refluxed at 80-90 C. for 34-38 hours. The reaction mixture was cooled to below 70 C. and acetonitrile (80.0 mL) was added. The reaction mixture was further cooled to 20-30 C. and filtered through celite prewashed with acetonitrile. The filtrate was concentrated at 50-60 C. under vacuum till viscous mass is obtained. The viscous mass was cooled to 20-30 C. Dichloromethane (320.0 mL) was added to the viscous mass under stirring and washed with potassium carbonate solution (32.0 g in 200 mL water). The organic layer was washed with DM water twice. The organic layer (Dichloromethane) was concentrated under vacuum at 35-40 C. till viscous mass is attained. The viscous mass was dried under vacuum at 35-40 C. for one hour. Ethyl acetate (160.0 mL) was added to the viscous mass and cooled to 0-5 C. and stirred for one hour. The solid separated out was filtered and washed with ethyl acetate. The isolated solid was dissolved in dichloromethane and concentrated the solution under vacuum at 35-40 C. till viscous mass. The viscous mass was dissolved in acetone and cooled to 0-5 C. under stirring. The solid separated out was filtered, washed with acetone and dried at 40-45 C. under vacuum for 4-6 hours to give the title compound (III, 30.1 g; 56.30%), with a purity of 97.22%.

The synthetic route of 3543-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, Computed Properties of C3H4N2

A mixture of KI (29.3 g,176.0 mmol) and I2 (22.4 g, 88.0 mmol) inwater (60 mL) was addedto a solution of 1H-imidazole (3.0 g, 44.1 mmol) in 2 M NaOH(10.6 g, 264.5 mmol). The mixture was stirred at 20 C for 3 h andthen neutralized with 6 M HCl (pH 7). The resulting solid wascollected by filtration, recrystallization from ethanol to give 2 as agrey solid (14.0 g, 99.0%). Mp 166e168 C. 1H NMR (300 MHz,DMSO-d6) d(ppm) 12.75 (br s, 1H), 7.8 (br s, 1H). MS (EI) m/z 320.8[MH].

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

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2620-76-0, These common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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.

3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenylboronic acid (10.0g, 0.028mol) in 2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole (8.0g, 0.023mol), Pd (PPh3) 4 (1.3g, 0.0011mol), into the THF in 400ml potassium carbonate (9.5g, 0.069mol) was reacted with stirring for 18 hours at 65 . After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to afford 85 12.1g (75percent yield).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PH Tech Pvt. Ltd.; Hyeon, Seo Young; Yun, Young Ho; Kim, Tae Hwan; Oh, Hyeon Jin; (36 pag.)KR101593465; (2016); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53710-78-4, The chemical industry reduces the impact on the environment during synthesis 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: mmol), ethyl chloroacetate (0.147 g, 2.4 mmol), K2CO3(0.28 g,4 mmol) and DMF(10 ml) was stirred at 6 C for 12 h. DMF wasremoved under reduced pressure and the residue was purifiedthrough a column chromatography on silica with chloroform/methanol (V:V 50:1) as a white solid (0.59 g, 95.2% yield).

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, 1-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fan, Yan-Hua; Li, Wei; Liu, Dan-Dan; Bai, Meng-Xuan; Song, Hong-Rui; Xu, Yong-Nan; Lee, SangKook; Zhou, Zhi-Peng; Wang, Jian; Ding, Huai-Wei; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 95 – 106;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1072-62-4, These common heterocyclic compound, 1072-62-4, name is 2-Ethyl-1H-imidazole, 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.

To a solution of 2-ethylimidazole (15.000 g; 156.03 mmol; 1.0 eq.) in dioxane (250 ml), and water (250 ml) was added at rt (in one portion) successively Na2CO3 (49.614 g; 468.10 mmol; 3.0 eq.), and iodine (87.126 g; 343.27 mmol; 2.2 eq.). The resulting brown heterogeneous reaction mixture was further stirred at rt, under nitrogen, for 24 h. AcOEt (500 ml) was then added followed by an aq. solution of sodium thiosulfate (45.0 g Na2S2O3 in 300 ml of water). The yellow organic layer was separated, and additionally washed with an aq. solution of sodium thiosulfate (30.0 g Na2S2O3 in 300 ml of water), and finally with brine (200 ml). The resulting yellow organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give 2-ethyl-4,5-diiodo-1H-imidazole as a pale yellow solid which was further dried under HV (49.760 g; 92%). LC-MS: tR=0.55 min.; [M+H]+: 349.18 g/mol.

Statistics shows that 2-Ethyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 1072-62-4.

Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (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. 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Cyclopropyl-1H-imidazole

[0415] Into a 20-mL microwave tube was added Example 55a (300 mg, 1.339 mmol), Example 55b (173 mg, 1,61 mmol), Cul (100 mg, 0.53mmol), K3P04 (567 mg, 2.68 mmol) and Nu’,Nu2- dimethylcyclohexane-l,2-diamine (75 mg, 0.53mmol) successively. DMF (6 mL) was added by syringe. The mixture was degassed by nitrogen for three times and sealed. The reaction was heated up to 150C by microwave for lh. LC-MS showed reaction completed. The reaction was filtered, washed by MeOH and purified by flash chromatography to afford Example 55c (110 mg, yield: 32.6%, crude) as a yellow solid. LCMS [M+l]+ = 252.0

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; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 219814-29-6, These common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, 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.

[Example 6]; While a mixture of 23.9 g (100.0 mmol) of 2,4-dibromo-5-methylimidazole, 29.4 g (300.0 mmol) of cyclohexanone, and 23.9 g (259.4 mmol) of toluene was stirred at ordinary temperature, 22.5 g (150.0 mmol) of sodium iodide was added thereto to prepare a reaction liquid. After the reaction liquid was stirred at 105C for 12 hours under a nitrogen stream, the liquid was stirred under ice cooling for 1 hour. When 2-bromo-4-methylimidazole in the reaction liquid was analyzed by means of HPLC, it was confirmed that the product was formed in an amount of 13.7 g (82.3 mmol, conversion: 85.3%). After the reaction liquid was concentrated under reduced pressure, the product was purified by silica gel chromatography (ethyl acetate/hexane system) and, after volatile matter was further vaporized to solidify the product, crystals of 2-bromo-4-methylimidazole were obtained in an amount of 12.6 g (yield: 78.1%) as a residue. Incidentally, the NMR spectrum of the crystals was measured and was compared with the NMR spectrum of its specimen, whereby it was confirmed that the product is 2-bromo-4-methylimidazole.

Statistics shows that 2,5-Dibromo-4-methylimidazole is playing an increasingly important role. we look forward to future research findings about 219814-29-6.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; EP2141151; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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. COA of Formula: C7H10N2O2

A. N-(2-Fluorophenyl)-5-methyl-1H-imidazole-4-carboxamide To ethyl-4-methyl-5-imidazolecarboxylate (5 g, 32.4 mmol) was added 20 mL of 2-fluoroaniline and potassium carbonate (8.9 g, 64.8 mmol). The reaction mixture was heated to reflux for 18 h then cooled to room temperature and concentrated in vacuo. Water and hexane were added and the precipitate filtered to give the crude product.

The synthetic route of Ethyl 5-methyl-1H-imidazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Co.; US6235740; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem