Category: imidazoles-derivatives

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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methyl-1H-benzoimidazol-5-ylamine

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

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:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, These common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-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.

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (801 mg, 4.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 5-bromo-1-methylimidazole (644 mg, 4.00 mmol) in 1 ,4-dioxane (30 ml) was added potassium phosphate (4246 mg, 20.00 mmol), trans- N,N-dimethylcyclohexane-1 ,2-diamine (0.631 ml, 4.00 mmol) and copper(l) iodide (762 mg, 4.00 mmol) and the mixture stirred at reflux overnight. The reaction mixture was diluted with dichloromethane and filtered through celite. The filter pad was washed with dichloromethane and the filtrate was reduced under vacuum. The residue was re-dissolved in dichloromethane, washed with 0.880 ammonia (x2), water then brine and passed through a hydrophobic frit and the solution was concentrated under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H-imidazol-5-yl)-2-oxo-4- imidazolidinecarboxylate (393 mg, 32.6 % yield). LC/MS [M+H]+ = 281.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Under ice-cooling, L-selectride (1.3 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (10 mi) solution containing (R)-6-[(S)-3,4-difluorophenyl]-l-metyltetrahydropyrrolo[2,1-c][1,4]oxazin-3,4-dione (297 mg). Stirring was continued for 1.5 hours at the same temperature. A 5 N sodium hydroxide solution (197 muL) was added to the reaction solution, and stirring was continued for 10 minutes at 0 C., and next hydrogen peroxide solution (96 muL, 35% solution) was added, and stirring was continued for 10 minutes at 0 C. Sodium bisulfite (103 mg) was added, and after stirring for 20 minutes at room temperature, 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 (10 mL) and triphenyl phosphonium bromide (345 mg) were 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 (235 mg) and triethylamine (274 muL) were added, and the resultant was stirred at room temperature for 20 hours. 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 a vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH and Chromatrex, eluting solvent: hexane/ethyl acetate?ethyl acetate?ethyl acetate/methanol), and the title compound (260 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 466 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.47 (d, J=6.8 Hz, 3H), 1.80-1.91 (m, 1H), 2.02-2.07 (m, 1H), 2.10-2.17 (m, 1H), 2.29 (s, 3H), 2.35-2.46 (m, 1H), 3.84 (s, 3H), 4.23-4.28 (m, 1H), 4.78-4.84 (m, 1H), 5.11 (d, J=9.6 Hz, 1H), 6.81 (s, 1H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 7.04-7.15 (m, 3H), 7.19 (d, J=8.0 Hz, 1H), 7.38-7.40 (m, 1H), 7.38 (s, 1H), 7.69 (d, J=1.2 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

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

Related Products of 36947-68-9, 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. 36947-68-9, name is 2-Isopropyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Isopropylimidazole (11 g, 0.10 mol) and sodium hydroxide (14 g, 0.35 mol) are dissolved in0.4 L water in a 1 L round bottom flask. Potassium iodide (80 g, 0.48 mol) and iodine (55 g,0.22 mol) are dissolved in 0.2 L water. This solution is added drop wise to the imidazole/sodium hydroxide mixture at room temperature. A white solid precipitates and the solution is stirred over night. Acetic acid and sodium thiosulfate are added until the solution is clear and neutral. The yellow solid is filtered and washed with water. Recrystallization from ethanolleads to fine white crystals. (16 g, 44 %).

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

Reference:
Article; Kunz, Peter C.; Thiel, Indre; Noffke, Anna Louisa; Reiss, Guido J.; Mohr, Fabian; Spingler, Bernhard; Journal of Organometallic Chemistry; vol. 697; 1; (2012); p. 33 – 40;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14813-85-5,Some common heterocyclic compound, 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C13H10N2O, 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.

1-phenyl-1,3-dihydro-benzimidazole-2-one, and 52g (250 mmol), in the first and K2CO3 of 38g (275 mmol), is introduced into the DMF of 100ml. After 1 hour at room temperature, it is added dropwise a solution of 2-bromobenzyl bromide 62g in DMF in 500 ml (250 mmol). The reaction mixture was then stirred for 25 hours at room temperature. After this time, the reaction mixture was poured onto ice, and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4, and evaporated. The residue was extracted with hot toluene, recrystallized from toluene / n-heptane. The yield is 65g (70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; PARHAM, AMIR HOSSAIN; PFLUMM, CHRISTOF; JATSCH, ANJA; EBERLE, THOMAS; KROEBER, JONAS VALENTIN; (86 pag.)JP2016/500675; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 63655-40-3, 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. 63655-40-3, name is 2-Amino-1H-benzo[d]imidazole-5-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of corresponding benzoyl chlorides 2-3 in drytoluene, a solution of 2-amino-5(6)-cyanobenzimidazole 29in dry toluene was added dropwise, followed by the additionof Et3N. The reaction mixture was refluxed for severalhours. After cooling the solution was concentrated and theobtained solid was filtered off and recrystallized fromappropriate solvent.

The synthetic route of 2-Amino-1H-benzo[d]imidazole-5-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cindri?, Maja; Sovi?, Irena; Martin-Kleiner, Irena; Kralj, Marijeta; Ma?ek, Tomislav; Hranjec, Marijana; Star?evi?, Kristina; Medicinal Chemistry Research; vol. 26; 9; (2017); p. 2024 – 2037;,
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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H7ClN2O

The starting material was synthesised as follows: 2-Chloro-5-methoxybenzimidazole (0.3 g, 1.64 mmol) was suspended in dichloromethane (20 ml) under argon followed by the addition of boron tribromide (233 ul, 2.46 mmol). The reaction mixture was stirred for 2 hours at ambient temperature. The solvent was evaporated and the resulting powder was added in portions to methanol (30 ml). Silica was added and the solvent was evaporated. The resulting powder was placed on the top of a silica column and the product was eluted off using dichloromethane/methanol (95/5). Evaporation of the solvent and trituration in ether gave 2-chloro-5-hydroxybenzimidazole (440 mg, 99%).

According to the analysis of related databases, 15965-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; EP1154774; (2005); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 28890-99-5, The chemical industry reduces the impact on the environment during synthesis 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, I believe this compound will play a more active role in future production and life.

5.00 g ( 36.0 mmol) 2,3-difluorobenzonitrile, 14.9 g (72.0 mmol) 6H-benzimidazolo[1 ,2- a]benzimidazole and 30.5 (144 mmol) potassium phosphate tribasic in 120 ml NMP (N-Methyl- 2-pyrrolidon) are stirred at 185 C under nitrogen for 6 h. The reaction mixture is filtered hot and the organic phase is poured on water. The product is filtered of. Column chromatography on silica gel with chloroform gives 6.25 g 33.9 % of the product. 1H NMR (300 MHz, DMSO-D6): rotamers: delta 8.43-8.57 (m, 2H), 7.58-8.20 (m, 6H), 6.86-7.42 (m, 9H), 6.63-7.78 (m, 1 H), 6.48-6.54 (m, 1 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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4887-88-1, The chemical industry reduces the impact on the environment during synthesis 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

5-Bromo-1H-benzo[d]imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% 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, 5-Bromo-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mortensen, Deborah S.; Perrin-Ninkovic, Sophie M.; Harris, Roy; Lee, Branden G.S.; Shevlin, Graziella; Hickman, Matt; Khambatta, Gody; Bisonette, Rene R.; Fultz, Kimberly E.; Sankar, Sabita; Bioorganic and Medicinal Chemistry Letters; vol. 21; 22; (2011); p. 6793 – 6799;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 67085-11-4, A common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, molecular formula is C13H15ClN2O, 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.

PREPARATION 7 A mixture of 1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]imidazole (20 g) in dry pyridine (100 ml) was cooled in an ice bath and treated dropwise with stirring with 7.0 ml of methanesulfonyl chloride. The mixture was allowed to come to room temperature overnight and diluted to 500 ml by the addition of ethyl acetate, with stirring. The resulting solid was then filtered off, washed with acetone and dried in air to give 1-[4-(4-chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride as a white solid (27.4 g).

The synthetic route of 67085-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Syntex (U.S.A.) Inc.; US4518607; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem