Month: January 2021

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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. category: imidazoles-derivatives

D. 1,1′-Bis-(3-methyl-imidazole)-1-sulfonyl triflate salt (1-F). To a solution of compound 1-E (1.26 g, 6.36 mmol) in CH2Cl2 (10 mL), cooled to 0 C., was added methyl triflate (0.719 mL, 6.36 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred for 18 hours. The solvent was evaporated under reduced pressure to afford compound 1-F as a 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 7189-69-7, its application will become more common.

Reference:
Patent; Matthews, Jay M.; US2010/160337; (2010); 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. 760212-58-6, name is 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole

500 ml three-neck bottle,Equipped with mechanical mixing and distillation unit,5.0 g (0.0091 mol) of the compound of the formula M-206 was added,3.49 g (0.0101 mol) of 4-(2-phenyl-1H-benzo[d]imidazol-1-yl)bromobenzene,40 ml of toluene,40 ml of ethanol,25 ml of water,2.51 g (0.0182 mol) of potassium carbonate,0.05 g (0.0000455 mol) of tetrakistriphenylphosphine palladium was added under nitrogen protection.After the addition, slowly warmed to 70 C,Reaction for 8 hours.Cool down, add water,The organic layer is washed,Dry over anhydrous sodium sulfate,Decolorization on silica gel column,The eluent is concentrated to dryness.The crude product P-2 was obtained.The above crude P-2 product was recrystallized from a mixed solvent of toluene and ethyl acetate to obtain 5.01 g of a product P-2.The yield was 71.3%.

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 760212-58-6.

Reference:
Patent; Fuyang Xinyihua Materials Technology Co., Ltd.; Wang Zhanqi; Li Zhiqiang; Guo Linlin; (37 pag.)CN108218788; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1219741-19-1, 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. 1219741-19-1, name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Step A: 6-chloro-5-iodo-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (0768) To a suspension of 6-chloro-5-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole (5.042 g, 14.14 mmol) in DCM (100 mL) at 0 C. was added TEA (2.96 mL, 21.21 mmol), and SEM-C1 (2.76 mL, 15.55 mmol) dropwise. The resulting solution was stirred from 0 C. for 1 hr. The reaction mixture was partitioned between water (200 mL) and DCM (100 mL), the aqueous phase was extracted with DCM (200 mL), and the combined organic phase was dried over anhydrous Na2SO4, concentrated and the residue was purified on silica gel column using EtOAc/hexane as eluting solvents to give the title compound. LC/MS: (M+1)+: 487.17.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 96797-15-8, 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. 96797-15-8 name is 4-Iodo-1-trityl-1H-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.

A. 2-fluoro-5- (l-trityl-lH-imidazol-4-yl)-pyridine. To a solution of 4- IODO-1-TRITYL-1H-IMIDAZOLE (10.0 g, 23 mmoles) in THF (100 ml) at room temperature was added ethylmagnesium bromide (28 ml, 27.5 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (3.8 g, 27.5 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (2.6 g, 2.3 mmoles) and 5-bromo-2- fluoropyridine (5.0 g, 27.5 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with an EDTA buffer (at approximate pH 9) (2x 300 ml), NACI (sat. ) (300 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash 40 chromatography using an initial solvent gradient of 99.5% DCM, 0.5% MeOH, and 0. 1% TEA (1 L), then a solvent gradient of 99% DCM, 1% MeOH, and 0. 1% TEA (1 L) to yield 2-FLUORO-5- (1-TRITYL-LH-IMIDAZOL-4-YL)-PYRIDINE (6.4g, 69%). MH (406)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
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. 37148-86-0, name is 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole

Step 1. 4-[4-(4-Trifluoromethylphenyl)-lH-imidazol-l-yl]-nitrobenzene. 4-Trifluoromethylphenyl imidazole (1.43 g, 6.7 mmol), 4-fluoro nitrobenzene (1.2 g, 8.5 mmol) and potassium carbonate (1.5 g, 10.9 mmol) were combined in DMF (15 mL) and heated at 100 0C for 6 h. The cooled solution was then poured onto water (100 mL), and the resulting solid was filtered and air-dried to give the title imidazole (1.0 g) as a light yellow solid: mp 197 0C. Anal. Calcd. for Ci6Hi0F3N3O2: C, 57.66; H, 3.02; N, 12.61. Found: C, 57.69; H, 3.01; N, 12.48.

The synthetic route of 37148-86-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (2011); 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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrN2

Step C-Methyl 5-(5-bromo-1H-henzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate and methyl 5-(6-bromo-1H-benzimidazol-1-yl)-3-{[tert-butyl(dimethyl)silyl]oxy}thiophene-2-carboxylate (Title Compounds)To a solution of crude, impure 5-bromobenzimidazole (48.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 ml, 350 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:bexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 4 eluting first and 29.2 g of Intermediate 5 eluting second (58%). (Intermediate 4, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.58(dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.78 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 5, 6-Br) 1H NMR (400 MHz, d6-DMSG) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77(s, 3H), 0.99 (s, 9H), 0.28 (s, 6H).

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 4887-88-1.

Reference:
Patent; Kuntz, Kevin; Emmitte, Kyle Allen; Rheault, Tara Renae; Smith, Stephon; Hornberger, Keith; Dickson, Hamilton; Cheung, Mui; US2008/300247; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2, name: 4-Bromo-1H-imidazole

General procedure: Amberlyst A21 (20 wt %) was added to a mixture of amine (1 mmole) and (Boc)2O (1 mmole) and the mixture was stirred for the appropriate reaction time as specified in (Table 1). The progress of reaction was monitored by Thin layer chromatography (10-20% ethyl acetate: hexane) on TLC plates (Merck) precoated with silica. After completion of reaction, the reaction mass was diluted with methanol, filtered off the catalyst which was washed for several times and then dried at 800 C under reduced pressure for 1 hour and subjected to further recycle study (Table 4). It showed no much more decrease in the product yield indicating high activity of the catalyst. The filtrate was concentrated on rotavacc and the product was purified by column chromatography to afford pure products.

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:
Article; Tekale, Sunil U.; Kauthale, Sushama S.; Pawar, Rajendra P.; Journal of the Chilean Chemical Society; vol. 58; 1; (2013); p. 1619 – 1623;,
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

2-Chloro-1H-benzimidazole (7.5 g, 49 mmol) was dissolved in dimethylformamide (20 mL),and the reaction mixture was cooled to oo C. Sodium hydride ( 60% dispersion in mineral oil 2.16 g,5 5.4 mmol) was carefully added. The reaction mixture was stirred at ambient temperature for 1 hour,and after that iodomethane (8.37g, 59 mmol) was added. The reaction mixture was stirred at ambienttemperature overnight, and then water (200 mL) was added. The solid was collected by filtration toafford 5 g, 61% of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 3.79(s, 3H), 7.21-7.33 (m, 2H), 7.58 (t, J=7.0 Hz, 2H).

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

Reference:
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); 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. 162356-38-9, name is 2-(2-Bromophenyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(2-Bromophenyl)-1H-imidazole

Example 20 2-[2-({4-[(2,4-difluorophenoxy)methyl]phenyl}sulfonyl)plienyl]-l/r-imidazole; 2-(2-Bromophenyl)-lH-imidazole (WO 9407486; 1.0 g, 4.48 mmol) was dissolved in TEtaF (11 mL) and DMF (11 mL) and cooled to 00C. Sodium hydride (60percent dispersion in mineral oil, 197 mg, 4.93 mmol) was added and the reaction stirred for 20 min. 2-(Trimethylsilyl)ethoxymethyl chloride (0.79 mL, 4.93 mmol) was added and the reaction stirred overnight at room temperature. The reaction was quenched with MeOH then partitioned between water and Et2O. The organic layer was dried over MgSO4 and EPO concentrated in vacuo. The residue was purified by flash column chromatography, then used according to the method of Example 15 Step 1, followed by SEM-deprotection using trifluoroacetic acid in dichloromethane, to give the title compound. 1H NMR (500 MHz, DMSO): delta 12.10 (1 H, s), 8.24 (1 H, d, J 6.9 Hz), 7.77-7.71 (2 H, m), 7.65 (2 H, d, J 8.0 Hz), 7.53-7.50 (3 H, m), 7.29 (1 H, t, J 8.6 Hz), 7.23- 7.18 (2 H, m), 6.99 (1 H, t, J 7.6 Hz), 6.90 (1 H, s), 5.20 (2 H, s); m/z (ES+) 427 [MH+].

According to the analysis of related databases, 162356-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2006/97766; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 37067-95-1,Some common heterocyclic compound, 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

HL3: 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (1.0 mmol), Pd(OAc)2 (0.05 equiv), PPh3 (0.2 equiv), 1-methyl-2-iodoimidazole (2.5 mmol) were resolved in dimethoxyethane/2M K2CO3 aqueous solution (20 mL, 1:1) under nitrogen atmosphere. The mixture was heated and refluxed for 24 h. After being cooled to room temperature, the reaction mixture was diluted with EtOAc, and poured into a brine solution. The organic layer was separated, and washed with the water, dried, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the pure product HL3 in 34% yield. 1H NMR (CDCl3): 3.72 (s 6H), 7.12 (d, 2H), 7.47 (t, 1H), 7.48 (d, 2H), 7.56 (s, 1H), 7.72 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Arizona Board of Regents for and on Behalf of Arizona State University; US2011/301351; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem