Category: 4857-06-1

Synthetic Route of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-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.

To a solution of 2-chloro-1H-benzo[d]imidazole (3.0019 g, 19.67 mmol, Sigma-Aldrich Chemical Company, Inc.) in 2.5 M sodium hydroxide solution (19.67 ml, 49.2 mmol, J. T. Baker) at 0 C. was added dimethyl sulfate (3.01 ml, 31.5 mmol, Riedel de Haen AG) dropwise. The reaction was allowed to stir for 1½ h. White precipitate was noted to form. The white precipitate was filtered, washed with water, and dried to give the title compound. LCMS showed product peak at 1.47 min (m+1=167.0). 1H NMR (400 MHz, DMSO-d6) delta ppm 3.80 (s, 3H) 7.21-7.28 (m, 1H) 7.28-7.35 (m, 1H) 7.59 (d, J=3.72 Hz, 1H) 7.61 (d, J=3.72 Hz, 1H)

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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.

Commercially available 2-chloro-1H-benzo[d]imidazole (250 mg, 1.64 mmol) was dissolved in DMF (4.7 mL), dimethylamine (50% aqueous solution, 0.50 mL, 4.92 mmol) was added, and the mixture was stirred with heating at 200C for 30 min in an Emrys Optimizer microwave synthesizer. Water was added to the mixture, and the precipitated crystals were collected by suction filtration to give N,N-dimethyl-1H-benzo[d]imidazole-2-amine (234 mg, 89%). ESIMS m/z: 162 (M + H)+; 1H NMR (270 MHz, DMSO-d6, delta): 3.03 (s, 6H), 6.79-6.97 (m, 2H), 7.07-7.20 (m, 2H), 11.17 (br 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 2-Chloro-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; YAMAMOTO, Keisuke; TAMURA, Tomohiro; NAKAMURA, Rina; UENO, Kimihisa; HOSOE, Shintaro; EP2740730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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. Product Details of 4857-06-1

(5) 0.078 mol of 2-chlorobenzimidazole was dissolved in 90 mL of dry N,N-dimethylformamide, and 0.079 mol of 60% sodium hydrogen was added in portions in an ice bath and under a nitrogen atmosphere, followed by an ice bath. Stir for 30 minutes under nitrogen atmosphere, add 0.079 mol of 2-(trimethylsilyl)ethoxymethyl chloride, react at 20C for 16 hours, and turn the reaction solution into a yellow suspension, ice bathUnder cooling, 200 mL of water was slowly added, extracted with ethyl acetate, the organic phases were combined, and after drying, petroleum ether: ethyl acetate was used as eluent at a volume ratio of 10:1 to separate 16 g of white solid compound VII. The yield was 71.93%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; Tierxi (Nanjing) Pharmaceutical Research And Development Co., Ltd.; He Xu; Hu Yongzhu; Zhang Chi; Liu Chun; Cui Xilin; (26 pag.)CN107663192; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-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.

2-Chloro-5,6-dibromobenzimidazole (17) To a suspension of 0.763 g (5 mmole) of 2-chlorobenzimidazole in 50 mL of 1:1 MeOH/H2 O, was added dropwise a solution of 1 mL of Br2 in 10 mL of MeOH over a period of 30 min. The reaction mixture was stirred at room temperature overnight and was then filtered. The solid was washed with portions of H2 O until the washings were neutral. This solid was air dried and recrystallized from MeOH to give 1.115 g (3 crops, 72%) of 17. mp 228 C.; 1 H NMR (DMSO-d6) d 13-14 (br. s, 1,1-NH), 7.93 (s, 2,4-H, 7-H).

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

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5ClN2

PREPARATION 2 (1-(4-Fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Combine 2-chloro-1H-benzimidazole (17.75 g, 116 mmol) and 4-fluorobenzyl bromide (26.6 g, 141 mmol) in dimethylformamide (100 mL). Add a solution of sodium hydroxide (50 g) in water (75 mL). (Caution, exothermic). After 30 minutes, pour the reaction mixture into water (1800 mL) and stir to form a solid. After 1 hour, collect the solid by filtration, dissolve the solid in dichloromethane, and extract with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluding with 5% ethyl acetate/dichloromethane to give a solid. Recrystallize from chloroform/hexane to give, after drying, 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole.

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; Aventis Pharmaceuticals Inc.; US6211199; (2001); B1;,
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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., name: 2-Chloro-1H-benzo[d]imidazole

Step 1: N-Phenyl-1H-benzo[d]imidazol-2-amine 2-Chloro-1H-benzo[d]imidazole (5 g, 32.8 mmol) was dissolved in N-methyl-2-pyrrolidone (NMP) (50 mL) and treated with aniline (3.3 mL, 36.1 mmol), followed by methanesulfonic acid (2.4 mL, 37.0 mmol). The resulting mixture was purged with N2 for 5 min, then heated at 100 C. for 18 h. The mixture was cooled to room temperature (?22 C.) then poured into a stirred mixture of saturated NaHCO3 (aq) (100 mL) in water (400 mL). The resulting suspension was extracted with ethyl acetate (2*75 mL). The organic phases were combined and washed sequentially with water (3*75 mL) and brine (75 mL), then dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil. The residue was dissolved in methyl tert-butyl (MTBE) (ca. 50 mL) and the product crystallised by slow addition of isohexane (ca. 25 mL) with periodic sonication. The resultant slurry was stirred at room temperature for 1 h, then the precipitate was collected by filtration, washing with MTBE/isohexane (1:1, 3*10 mL), and drying in vacuo to afford N-phenyl-1H-benzo[d]imidazol-2-amine (6.25 g, 89%). The precipitate was a pale pink crystalline solid.

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; Universal Display Corporation; LIN, Chun; Ji, Zhiqiang; Ma, Bin; (139 pag.)US2018/337344; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 4857-06-1 as follows. Application In Synthesis of 2-Chloro-1H-benzo[d]imidazole

Example 1N-(4-Fluoro-3-trifluoromethyl-benzyl)-N-(1-methyl-1H-benzimidazol-2-yl)-benzenesulfonamide (Compound No.15)Step A: 2-Chloro-1-methyl-1H-benzimidazoleTo a solution of 2-chloro-1H-benzimidazole (5.03 g, 33.0 mmol) in anhydrous DMF (33 mL) at 0 C. was added portion-wise 95% NaH (871 mg, 36.3 mmol). The ice bath was removed and the resulting mixture was stirred at room temperature for 1 h. Iodomethane (4.68 g, 33.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The resulting mixture was then diluted with water, and the resulting precipitate was collected by filtration and purified by recrystallization from hexane to yield 2-chloro-1-methyl-1H-benzimidazole. MS 167 (M+1)+

According to the analysis of related databases, 4857-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jetter, Michele C.; Macielag, Mark J.; Xia, Mingde; Xu, Xiaoqing; US2011/3801; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (purity 55%)(516 mg, 12.0 mmol) was added to a N,N-dimethylformamide solution (8.0 ml) of 2-chloro-1H-benzimidazole (1.52 g, 10.0 mmol), at 0C, under nitrogen stream, and stirring was carried out for 20 minutes. Methyl iodide (0.750 ml, 12.0 mmol) was further added, and stirring was carried out under room temperature for 2 hours. Water was added to the reaction solution, and the resulting solid substance was collected by filtration to afford 2-chloro-1-methyl-1H-benzimidazole (1.51 g, yield 91%) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2258697; (2010); 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-1H-benzo[d]imidazole

(2) Synthesis of intermediate (C-2); [0080][Chem. 12] Intermediate (C-2); [0081] 2-Chloro-benzimidazole (20 g (131 mmol, trade name: 2-Chlorobenzimidazole, manufactured by Aldrich) and THF (150 mL) were placed in a 500-mL three-neck flask, and t-butoxy sodium (13.8 g (144 mmol)) was added thereto under ice cooling. The mixture was stirred at room temperature for 1 hour. Subsequently, a solution of methyl iodide (24.2 g (170 mmol)) and THF (30 mL) was dropped into the flask under ice cooling, and the resulting mixture was stirred at room temperature for 5 hours. The reaction solution wasextracted with chloroform, followed by drying over anhydrous sodium sulfate. Subsequently, the solvent was removed to obtain 18.6 g (yield: 85%) of an intermediate (C-2) (2- chloro-1 -methyl- lH-benzimidazole, white crystal) .

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; CANON KABUSHIKI KAISHA; MUTA, Hajime; SEKIGUCHI, Takeshi; ISHII, Ryuji; SUZUKI, Koichi; WO2011/122381; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 4857-06-1, name is 2-Chloro-1H-benzo[d]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 4857-06-1, Computed Properties of C7H5ClN2

Step3: Under nitrogen protection,Add to the reaction vessel2-chlorobenzimidazole (1.41 g, 9.2 mmol),Phenylboronic acid (1.02 g, 8.4 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL,20mL of ethanol and 20mL of distilled water,Stir at 120 ° C for 3 h.After the reaction is over, the distilled water stops the reaction.Extracted with ethyl acetate,The organic layer was dried over MgSO 4The solvent was removed by distillation under reduced pressure.After purification by silica gel column chromatography, Intermediate 77-3 (1.22 g, 75percent).

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:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (34 pag.)CN108822041; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem