Imidazoles-derivatives

Electric Literature of 17325-26-7, 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 17325-26-7 as follows.

A mixture of l ,3-dibromo-5-iodo-2-methoxybenzcnc (C) (Chae, J.; Buchwald, S. L. J. Org. Chem. 2004, 69, 3336-3339) ( 1.6 g, 4.1 mmol), methyl 4-imidazolecarboxylate (0.56 g, 4.4 mmol), cesium carbonate (1.31 g, 4.02 mmol) and 4A molecular sieves (0.88 g) in anhydrous DMF (20 tnL) was stirred under nitrogen for 15 min. Copper(II) trifluoromcthanesulfonate (50 mg, 0.14 mmol) was added and the reaction was stirred at 1 10 0C for 12 h. After cooling, the mixture was filtered and the filtrate was evaporated. The residue was treated with water and extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated. The residue was purified by flash chromatography to give methyl l-(3,5-dibromo-4-methoxyphenyI)-l H-imidazole-4-carboxylate (D) (0.21 g, 13%). 1H NMR delta (ppm)(DMSO-d6): 3.83 (3 H, s), 3.87 (3 H, s), 8.24 (2 H, s), 8.47 (1 H, d, J = 1.38 Hz), 8.62 ( 1 H, d, J = 1.39 Hz).

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSTITUTE FOR ONEWORLD HEALTH; JONES, Graham Peter; DOYLE, Kevin James; WO2010/33626; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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. Recommanded Product: 7189-69-7

Zn(NO3)26H2O (75 mg, 0.25 mmol), sdi (10 mg, 0.05 mmol) andmalonic acid (52 mg, 0.05 mmol) were mixed in 5 mL of methanol.The pH of the solution was adjusted to 5.0 by the addition of HNO3solution. The mixture was stirred for 30 min at room temperatureand filtered into a glass tube. Colorless crystals of 2 were obtainedin 5 days and collected by filtration, washed with water, and thendried in air. 89% yield (based on sdi). Anal. calcd (%): C, 23.17; H,2.57; N, 22.53. Found (%): C, 23.02; H, 2.64; N, 22.39. IR (KBr, cm1):3447 (m), 3126 (m), 2426 (w), 1637 (m), 1552 (m), 1456 (m), 1384(s), 1206 (m), 1165 (m), 1061 (m), 932 (m), 839 (m), 735 (m), 642(m), 619 (m), 575 (m).

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

Reference:
Article; Liu, Kang; Hu, Hanbin; Sun, Jing; Zhang, Yiheng; Han, Jishu; Wang, Lei; Journal of Molecular Structure; vol. 1134; (2017); p. 174 – 179;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, 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 144689-93-0 as follows.

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons). Step II: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid (Ve i); A solution of NaOH (0.052 g, 0.001311 mol> in water (1 mL) was added to compound (VdO (0.262 g, 0.0004337 mol) in THF (1 mL). The mixture was stirred at room temperature for 23 hrs (TLC monitoring: CH2Cl2/MeOH/AcOH 85:10:5). HCl IN was added until pH 4 was reached. The mixture was extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vei) (0.261 g) as a white solid, m.p. 68-69C. Yield: 99%. 1H-NMR (400 MHz, CDCl3, delta): -0.05 (s, 9H, Me3Si), 0.86 (t, J-7.2Hz, 3H, CH2CH2CH3), 0.89 (t, J=8.1etaz, 2H, SiCH2CH2O), 1.54-1.60 (m, 2H, CH2CH2CH3) 1.67 (s, 6H, CMe2), 2.94 (t, J-7.2Hz, 2H, CH2CH2CH3), 3.65 (t, J=8.1Hz, 2H, SiCH2CH2O), 5.75 (s, 2eta, ArCH2N), 5.79 (s, 2H, OCH2N), 6.97-6.99 (m, 2H) 7.12-7.14 (m, 2H) 7.35-7.38 (m, IH) 7.44-7.53 (m, 2H) 7.83-7.85 (m, IH) (aromatic protons). Step III: 4-Bromomethyl-5-methyl~l,3-dioxol~2-one; A mixture of 4,5-dimethyl-l,3-dioxol-2-one (1.5 g, 0.013158 mol), NBS (2.34 g, 0.013158 mol) and benzoyl peroxide (0.089 g, 0.0003684 mol) in CCl4 (20 mL) was stirred at 77C for 6 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The solution was treated with an aqueous solution OfNaHCO3 and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to give 4-bromomethyl-5 -methyl- 1,3- dioxol-2-one (2.34 g). Yield: 92%.1H-NMR (400 MHz, CDCl3, delta): 2.13 (s, 3H, CH3), 4.18 (s, 2H, CH2Br). Stp IV: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2~hydroxypropan-2-yl)-2-propyl-3-[[4- [2-(N-(2-trimethylsilylethoxymethyl)tetrazol-5-yl)pherpsil]phenyl]methyl]imidazole-4- carboxylate (Vf1); A mixture of the compound (Ve1) (0.260 g, 0.0004516 mol), 4-bromomethyl-5-methyl-l,3- dioxol-2-one (0.1 g, 0.000518 mol) and K2CO3 (0.033 g, 0.000239 mol) in anhydrous DMF (1.5 mL) was stirred for 1.5 hrs at room temperature under N2 atmosphere (TLC monitoring: CH2Cl2/Me0H/Ac0H 85:10:5). The mixture was partitioned between a saturated solution of NaHCO3 and AcOEt. The organic phase was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give the compound (Vf1) (0.3042g) as a yellow oil. Yield: 98%.1H-NMR (400 MHz, CDCl3, delta): -0.02 (s, 9H, Me3Si), 0.92 (t, J=8.1Hz, 2H, SiCH2CH2O), 0.98 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.64 (s, 6eta, CMe2), 1.70-1.80 (m, 2H, CH2CH2CH3), 2.07 (s, 3H, CH3C=C), 2.76 (m, 2H, CH2CH2CH3), 3.67 (t, J=8.1Hz, 2H, SiCH2CH2O), 4.89 (s, 2eta, COOCH2), 5.41 (s, 2H, ArCH2N), 5.79 (s, 2H, OCH2N), 6.80-6.82 (m, 2H) 7.14-7.16 (m, 2H) 7.44-7.52 (m, 2H) 7.54-7.58 (m, IH) 7.85-7.87 (m, IH) (aromatic protons). Step V: (5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)~2~propyl~3-[[4- [2~(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medo…

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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