Tag: M.W=200-300

Reference of 10040-96-7, 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. 10040-96-7, name is 1-(4-Bromophenyl)imidazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 21 (0.212 g, 1.12 mmol), CuI (20 mg, 0.112 mmol), (PPh3)2PdCl2 (40 mg, 0.056 mmol) and triethylamine (0.23 mL, 1.68 mmol) in acetonitrile (10 mL) was added 1-(4-bromophenyl)imidazole (0.5 g, 2.24 mmol). The reaction mixture was recharged with argon and stirred at 80 C for 3 h in a sealed tube. The mixture was extracted with ethyl acetate and the organic layer was washed successively with water and brine. The organic solvent was removed in vacuum. The residue was purified by column chromatography on silica gel (CH2Cl2/PE/NH3?H2O, 8:3:0.1) to afford 22c (0.3354 g, 1.01 mmol, 90.2%).HRMS (ESI) (M+H)+ m/z 332.1389, Calcd for C20H18N3O2 332.1394. 1H NMR (CDCl3, 400 MHz), delta: 7.93 (s, 1 H, H-imidazolyl), 7.55 (d, J = 8.1 Hz, 2 H, H-phenyl), 7.45-7.29 (m, 9 H, H-imidazolyl, H-phenyl), 5.25-5.15(m, 3 H, -NH-, -CH2-O-), 4.28 (s, 2 H, -NH-CH2-).

The chemical industry reduces the impact on the environment during synthesis 1-(4-Bromophenyl)imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Li, Xue-Meng; Lv, Wei; Guo, Si-Yang; Li, Ya-Xin; Fan, Bing-Zhi; Cushman, Mark; Kong, Fan-Sheng; Zhang, Jun; Liang, Jian-Hua; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 235 – 254;,
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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. 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H9N3O3

Synthesis of SYN-E; Formation of the dispersion synergist SYN-E was accomplished by diazotation of compound 7 and subsequent coupling with compound 3. [Show Image] 17.3 g (0.1 mol) of compound 7 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 98 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, 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 152628-03-0, name: 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid

1.2 kg of isoamyl alcohol was added to the reaction flask.Add 2-n-propyl-4-methyl-6-carboxybenzimidazole (400 g, 1.83 mol) and stir.Methanesulfonic acid (176 g, 1.83 mol, 1.0 eq) was added and N-methyl-phenylenediamine hydrochloride (360 g, 1.85 mol) was added.The temperature was raised to 130-135 C to reflux and the reaction was carried out for at least 18 hours until no significant moisture was separated. After the reaction is completed, cool to about 70 C,Add 2000 ml of water, stir, adjust the pH to 6~7 with 30% NaOH solution, stir and cool to 20~25 C after completion, and filter to obtain the product, the yield is 93.0%, and the HPLC purity is 99.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Weihai Disu Pharmaceutical Co., Ltd.; Disha Pharmaceutical Group Co., Ltd.; Li Xinfa; Cui Dapeng; (6 pag.)CN104974096; (2019); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 84946-20-3, 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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]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.

General procedure: A mixture of 1d (1.0 eq.) and ethanolamine (10 eq.) was heated to 150 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with diethyl ether. The crude product was purified by flash column chromatography (MeOH/methylene chloride) to give desired product 1e.

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

Reference:
Article; Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 395 – 403;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 152628-03-0, 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. 152628-03-0 name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, 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.

7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid methyl ester (7a): Sulfuric acid (12 mL, 0.22 mol) was added to 7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30 g, 136 mmol) dissolved in MeOH (670 mL, 16 mol). The mixture was refluxed for 36 hours and concentrated in vacuo. The recovered material was dissolved in 500 mL EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated to provide Intermediate (7a) as a brown solid (29.1 g). MS m/z: [M+H+] calcd for C13H16N2O2, 233.1; found 233.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Theravance, Inc.; US2008/318951; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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. Recommanded Product: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

The 3 – (4 – methyl – 1H – imidazole -1 – yl) -5 – trifluoromethyl aniline free base (12.0 g, 50 mmol, purity 88.5%) dissolved in methanol (54 ml) and acetone (270 ml) in the mixed solvent,. 25 – 30 C lower, adding concentrated hydrochloric acid (5.43 g, 55 mmol). The temperature slowly, about 15 – 20 C precipitated solid, lowering the temperature to – 10 – – 5 C stirring 2 hours, filtering, and washing the filter cake with cold acetone, 80 C and 10 – 20 mm Hg pressure drying to constant weight, to obtain the hydrochloride of crystalline form A solid 11 g, moisture 0.19%, purity 99.69%. Its X-ray powder diffraction pattern as shown in Figure 1; its heats analysis chart as shown in Figure 2.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Chuangnuo Pharmaceutical Co., Ltd.; Anlite (Shanghai) Pharmaceutical Technology Co., Ltd.; Shanghai Chuangnuo Pharmaceutical Group Co., Ltd.; Niu Deliang; Ma Bojun; Zhu Zhanqun; Wan Qiang; (10 pag.)CN108530364; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

116343-89-6, name is Methyl 1-phenyl-1H-imidazole-4-carboxylate, 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. Quality Control of Methyl 1-phenyl-1H-imidazole-4-carboxylate

LiOH.H2O (143 mg, 3.4 mmol) was added to a stirred solution of 1-phenyl-1H-imidazole-4-carboxylic acid methyl ester (231 mg, 1.1 mmol) in a mixture of THF (3 mL), MeOH (1 mL), H2O (1 mL) and stirring was continued at ambient temperature for 3 hrs. The reaction mixture was concentrated under reduced pressure. Cold water was then added and acidified it with 10% aqueous HCl, the solid was collected to afford 180 mg (83.7% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid.

The synthetic route of 116343-89-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forest Laboratories Holdings Limited; US2009/239810; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 14741-71-0, 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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) containing triethylamine (0.50 mL) phenylisothiocyanate (1.30 g, 0.01 mol) was added. The reaction mixture was heated under reflux for 4 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Yellow crystals from ethanol; yield: 2.67 g (87%); m.p. 202 oC. IR, : 3057 (CH aromatic), 2980 (CH2), 1689 (CO), 1643 (C=N), 1632 (C=C).1H-NMR: : 5.90 (s, 2H, pyrimidine CH2), 7.26-7.38 (m, 9H, C6H4, C6H5). 13C NMR (DMSO): 54.2 (CH2), 120.3, 123.7, 124.1, 124.6, 124.9, 125.8, 129.3, 126.7, 127.2, 128.2 (C6H5, C6H4), 163.4 (CO), 173.6 (C=N), 180.3 (C=S); Anal. calcd for C16H11N3OS: C, 65.51; H, 3.78; N, 14.32; S, 10.93%. Found: C, 65.33; H, 4.02; N, 14.59; S, 11.27%. MS: m/z: (%) 293 (M+, 22%).

The synthetic route of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

A solution of t-BuOK (1 M in THF, 0.80ml) was added dropwise to a stirred mixture of B6 (R7 = p-SF5-Phenyl and R6 = carboethoxyl, 0.41 g) and A1(157 mg, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol-1 -yl) and R8 = H) in 10 ml_ of anhydrous THF at -70eC under nitrogen atmosphere. The reaction mixture was stirred between -709C and -30QC until starting material were consumed. The reaction was quenched with iced brine, and extracted with EtOAc. The organic phase was washed with aqueous NH4CI and brine, dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by a flash silica gel column and eluted with DCM/MeOH to give 0.38g B7 (R7 = p-SF5-Phenyl, R6 = carboethoxyl, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol- 1-yl)).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; XU, Ruo; CLADER, John, W.; WO2010/54064; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

A tetrahydrofuran (20 mL) solution containing (1S,6R,9aR)-6-(4-chlorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione (685 mg) was cooled to -30 C. L-selectride (3.01 mL, 1.02 M tetrahydrofuran solution) was added dropwise, and stirring was continued for 2 hours at -20 C. to -30 C. 5 N sodium hydroxide solution (460 muL) was added to the reaction solution, and stirring was continued for 20 minutes at -20 C. to 0 C. Next, hydrogen peroxide solution (221 muL, 35% solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (237 mg) was added, and after stirring at room temperature for 20 minutes, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (19.4 mL) and triphenylphosphonium bromide (796 mg) was added to the residue, and the resultant was heated under reflux for 2 hours. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (543 mg) and triethylamine (633 muL) were added, and stirring was continued for 12 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate), and the title compound (640 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 480 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.48 (d, J=6.4 Hz, 3H), 2.29 (s, 3H), 3.51 (dd, J=11.2, 11.2 Hz, 1H), 3.74 (dd, J=12.0, 8.0 Hz, 1H), 3.83 (s, 3H), 3.99 (dd, J=11.2, 4.0 Hz, 1H), 4.18 (dd, J=12.4, 4.8 Hz, 1H), 4.41 (ddd, J=11.6, 4.0, 4.0 Hz, 1H), 4.50-4.56 (m, 1H), 4, 86 (dd, J=8.0, 4.4 Hz, 1H), 7.82 (s, 1H), 6.91 (s, 1H), 7.18 (d, J=8.8 Hz, 1H), 7.32-7.35 (m, 6H), 7.69 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, its application will become more common.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem