Category: imidazoles-derivatives

Reference of 84946-20-3, These common heterocyclic compound, 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]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.

EXAMPLE 42 To a 25 mL 3-neck flask equipped with a thermometer, reflux consenser and stir bar were added, under a nitrogen atmosphere, 885.6 mg (4.8 mmol) of Compound XXII, obtained according to the procedure of Example 41, and 0.93 mL (8.0 mmol) of lutidine. The mixture was heated to 120 C., whereupon a solution of 1.04 g (4 mmol., 1 eq.) of Compound X (Aldrich Chemical Co., Milwaukee, Wis.), 8 mmol of tetrabutylammonium fluoride (obtained from its 1.0M THF solution by distillation under vacuum with anhydrous toluene) and 4 mL of N-methylpyrrolidinone was added slowly over 2 h. The reaction mixture was allowed to stir at 120 C. for 1 h. High-performance liquid chromatography revealed >95% coversion to Compound XXIII. The reaction mixture was allowed to cool to ambient temperature, and slowly poured into a solution of 5% aqueous NaOH while stirring. The resulting suspension was allowed to stir at 0-10 C. for 30 minutes, and the resulting solid product was collected by vacuum filtration, washed with water (3*5 mL), and air dried for 30 minutes under vacuum to afford crude Compound XXIII: 1 H NMR (300 MHz, CDCl3) delta7.52 (1H, d, J=7.8 Hz), 7.20-7.00 (7H, m, two groups), 5.13 (2H, s), 4.40 (1H, NH br. d), 4.32 (2H, pseudo d), 4.20 (1H, m), 3.00 (2H, pseudo t), 2.15 (2H, pseudo d), 1.30 (2H, m overlapped), 1.26 (9H, s); 13 C NMR (75 MHz, CDCl3) delta176.3, 164.2 and 161.0 (13 C-19 F coupling), 153.3, 142.4, 134.6, 131.4, 128.4, 121.7, 120.0, 116.6, 116.4, 116.1, 107.5, 50.5, 45.1, 44.2, 38.9, 33.1, 28.6. It is to be noted that under the same reaction conditions as above, but without the use of tetrabutylammonium fluoride, only 3.5% conversion (high-performance liquid chromatography) to Compound XXIII was achieved after 3 h at 120 C. The Compound XXIII obtained above was placed in a 50 mL, 3-neck flask equipped with a thermometer, reflux condenser and stir bar. 5 mL of 48% hydrobromic acid was added, and the resulting mixture was heated to 110 C. and allowed to stir at that temperature for 2 h. After the reaction was complete (>98% conversion to norastemizole as shown by high-performance liquid chromatography), the reaction mixture was allowed to cool to room temperature, and 10 mL of toluene and 10 mL of water were added, with stirring.

The synthetic route of 84946-20-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sepracor Inc.; US5817823; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-42-2,Some common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, molecular formula is C4H5N3O2, 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 compound 1(2.9 g, 22.83 mmol) in THF (35 mL) was added LiHMDS (1.0 M THF solution, 24 mL, 24 mmol) at -40 C under argon. The mixture was stirred at -40 C for 15 minutes.The aldehyde was added slowly with inner temperature kept below -30 C. The mixture was stirred at – 40 C for 75 minutes before quenched with aqueous saturated NH4C1 solution (10 mL).The reaction mixture was extracted with EtOAc (40 mL x 3), washed with brine (50 mL), dried over Na2504.The solvents were removed under reduced pressure and the residue was purified via flash column to afford clear oil (1.5 g, yield 33%).1HNJIVIR (CDC13, 400 IVIHz) : 7.97 ( s, 1H), 4.22 (m, 1H), 4.00 (s, 3H), 2.24-2.14 (m, 1H), 1.06 (d, J = 6.4 Hz, 3H), 0.93 (dd, J = 1.2, 6.4 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-5-nitroimidazole, its application will become more common.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; MATTEUCCI, Mark; CAI, Xiaohong; CAO, Yeyu; JIAO, Hailong; MA, Jing Yuan; DUAN, Jian-Xin; (52 pag.)WO2016/210175; (2016); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

First, 4-imidazole formaldehyde (1a, 960 mg, 10 mmol) was added to the reaction flask.Place in an ice water bath. After 10 min, triethylamine (TEA) (278 mul, 2.0 mmol) was added to the reaction flask, and the mixture was stirred in the ice water bath for 5 min.Di-tert-butyl dicarbonate (2.4 g, 1.0 mmol) was then added to the reaction flask, and the reaction was moved to room temperature to react overnight.After the reaction was detected to be complete by TLC, the solvent was spin-dried and alumina column chromatography (PE: EA = 2: 1) was used to obtain intermediate 1b.

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 3034-50-2.

Reference:
Patent; Xihua University; Yang Lingling; Wang Zhouyu; Qian Shan; Li Ling; Xu Wei; Yang Huan; Liu Siyan; Yao Hao; Yan Jie; Li Chao; (21 pag.)CN110294713; (2019); 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Imidazole-4,5-dicarboxylic acid

In H2O (12ml) solvent, was added CuCl (0.841g, 0.85mmol), 2,2′-bipyridine (0.086g, 0.5mmol), 4,5-imidazole acid (0.078g, 0.5mmol), NaOH (0.020 g, 0.5mmol), placed on a magnetic stirrer was stirred for 30 minutes, the reaction was placed in 25ml teflon-lined autoclave, sealed in a high temperature oven, constant-temperature 160 C for five days to 5 C / h rate down to room temperature, a blue precipitate in the reactor bulk crystal, in 60% yield (based on copper).

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; Capital Normal University; Lu, Xiaoming; Cheng, Yifeng; (14 pag.)CN103965224; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 7: (3-(4-1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(1-methyl-1H-imidzol-5-yl)methanolA solution of n-BuLi (2.5 M in hexanes, 0.4 mL, 1 mmol) was added dropwise by syringe to a solution of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (0.500 g, 1.15 mmol, Intermediate 4: step c) in dry THF (13.5 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (141.6 mg, 1.286 mmol) in dry THF (0.2 mL) was added dropwise. The reaction was stirred for 5 minutes and moved to an ice bath for 1.5 hours before allowing the reaction to warm to room temperature. The reaction was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The combined organic phase was dried (Na2SO4), filtered, and concentrated. Crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM), followed by reverse-phase chromatography (acetonitriIe H2O + 0.05% TFA). Product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2SO4), filtered, and concentrated to provide the title compound. 1H NMR (400 MHz, CD3OD) delta ppm 8.43 (s, 1H), 8.12 (d, J = 2.4 Hz, 1H), 7.96 (dd, J = 8.7, 3.8 Hz, 1H), 7.83 (dd, J = 8.7, 1.6 Hz, 1H), 7.66 (dd, J = 9.6, 2.2 Hz, 1H), 7.62 (d, J = 8.8 Hz, 3H), 7.30 (dd, J = 12.9, 6.5 Hz, 2H), 6.56 (s, 1H), 6.48 (t, J = 2.1 Hz, 1H), 6.14 (s, I H), 4.57 (d. J = 6.1 Hz, 2H), 3.69 (s, 3H); MS m/e 464.1 [M+H]+

Statistics shows that 1-Methyl-1H-imidazole-5-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 39021-62-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi, A.; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; WO2015/57206; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

Ten (10) mL of a 36% aqueous solution of formaldehyde was added to a solution containing 1.00 g of A- trifluoromethylimidazole and 0.4 mL of a 10% tetra-n- butylammonium hydroxide solution in 10 mL of tetrahydrofuranat room temperature. The mixture was stirred at the same temperature for 14 hours and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain crude 4- trifluoromethylimidazol-1-ylmethanol . The crude product was dissolved in 20 mL of chloroform and thereto 0.8 mL of thionyl chloride was added at room temperature. The mixture was stirred under reflux conditions for 16 hours, allowed to be cooled to room temperature, and then concentrated under reduced pressure. The resultant residue was dissolved in 20 mL of tetrahydrofuran and thereto 940 mg of S- (3, 3, 3-trifluoropropyl) benzenethioate was added. To the solution, 2.4 mL of a 28% solution of sodium methoxide in methanol was added dropwise at room temperature. After stirring at the same temperature for 10 hours, to the reaction mixture was added 10% hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain 800 mg of 4-trifluoromethyl-1- [ (3, 3, 3- trifluoropropylsulfanyl) methyl] -lH-imidazole (hereinafter referred to as the present compound (3)) . The present compound (3) : 1H-NMR (CDCl3, TMS): delta (ppm) 7.65 (IH, s), 7.43 (IH, s), 5.01 (2H, s), 2.67-2.71 (2H, m) , 2.27-2.381 (2H, m) .

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/28727; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 56248-10-3, 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. 56248-10-3, name is 5-Phenyl-1H-imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Aromatic/heteroaromatic aldehydes a-l(1.0 mmol) was added to ethanol (2 mL) containingcompound 3 (100 mg, 0.40 mmol) and heated toreux point for 1h. The solids obtained was flteredand slurred with ethanol (1mL) followed by n-Hexaneto get the hydrazones 4a-l .

The synthetic route of 5-Phenyl-1H-imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rambabu, Namala; Ram, Bhavani; Dubey, Pramod Kumar; Vasudha, Bhavani; Balram, Bhavani; Oriental Journal of Chemistry; vol. 33; 1; (2017); p. 226 – 234;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 7189-69-7, The chemical industry reduces the impact on the environment during synthesis 7189-69-7, name is 1,1′-Sulfonyldiimidazole, I believe this compound will play a more active role in future production and life.

Compound B4 (137 mg, 0.240 mmol) obtained in Step 1 of Example 42 was suspended in toluene (2.4 mL), 1,1?-sulfonyldiimidazole (190 mg, 0.960 mmol) was added, and the mixture was refluxed for 6 days. A 1 mol/L aqueous sodium hydroxide solution was added to the reaction mixture. Extraction with dichloromethane and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: 100%) to give Compound B8 (19.3 mg, 13% 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, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; Fukuda, Yuichi; Kanai, Toshimi; Nakasato, Yoshisuke; Kimpara, Keisuke; US2013/65905; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 10040-96-7, name is 1-(4-Bromophenyl)imidazole, molecular formula is C9H7BrN2, 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. Application In Synthesis of 1-(4-Bromophenyl)imidazole

General procedure: To a solution of 1-(4-bromophenyl)-N, N-dimethylmethanamine (23.2 mg,0.108 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos)(10.4 mg, 0.018 mmol) and tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (8.3mg, 9.6 mumol) in 1,4-dioxane (1 ml) were added to compound 5(38.2 mg, 0.090 mmol) and N,N-diisopropylethylamine (31.4 mul, 0.180 mmol)and refluxed for 3 h. The mixture was filtrated by either Chromatodisc(0.45 mum) (KURABO INDUSTRIES, Osaka, Japan) or celite. The filtered solidwere washed with MeOH three times and then the assembled solution wasconcentrated under reduced pressure. The resulting residue was purified bypreparative TLC (CHCl3/MeOH/28% aq. NH4OH=10/1/0.1) to obtain thetitle compound as an off-white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10040-96-7, its application will become more common.

Reference:
Article; Wakiyama, Yoshinari; Kumura, Ko; Umemura, Eijiro; Masaki, Satomi; Ueda, Kazutaka; Sato, Yasuo; Watanabe, Takashi; Hirai, Yoko; Ajito, Keiichi; Journal of Antibiotics; vol. 70; 1; (2017); p. 52 – 64;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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 104619-51-4, HPLC of Formula: C7H7N5

To a 5 mL microwave tube was added a solution of tert-butyl 3-((2-(N,N-bis(4- methoxybenzyl)sulfamoyl)-4-(2,3 -diaminopyridin-4-yl)-3 -(2-(4-methoxybenzyl)-2H-tetrazol-5 – yl)phenyl)sulfonyl)azetidine- 1 -carboxylate (82mg, 0.090 mmol) and di( 1H-imidazol- 1- yl)methanimine (14.5 mg, 0.090 mmol) in toluene (5 ml). The mixture was stirred at 100C for 2hr. The solvent was removed in vacuum and the residue was purified by columnchromatography (ISCO RediSep Gold column 24 g) using 0-20% methanol/DCM as mobile phase to get the desired product. LC/MS (M+H): 938.60.

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, Di(1H-imidazol-1-yl)methanimine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, Frank; JIANG, Jinlong; PASTERNAK, Alexander; DONG, Shuzhi; GU, Xin; SCOTT, Jack D.; TANG, Haiqun; ZHAO, Zhiqiang; HUANG, Yuhua; HUNTER, David; YANG, Dexi; ZHANG, Zhibo; FU, Jianmin; BAI, Yunfeng; ZHENG, Zhixiang; ZHANG, Xu; YOUNG, Katherine; XIAO, Li; (580 pag.)WO2016/206101; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem