Tag: M.W=300-400

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. 15813-09-9, name is 4,5-Diiodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H2I2N2

A mixture of 2 (12.0 g, 37.5 mmol)and Na2SO3 (23.6 g, 187.3 mmol) in EtOH (120 mL) and H2O (20 mL)was refluxed for 72 h. The mixture was concentrated in vacuo andthe residue was extracted with ethyl acetate. The crude productwas purified by recrystallization from dichloromethane to afford 3as a white solid (3.5 g, 48.1%). Mp 137e139 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 7.0 (s, 1H), 7.5 (s, 1H). MS (EI) m/z 194.9[MH].

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 15813-09-9.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1219741-19-1, 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. 1219741-19-1 name is 5-Chloro-6-iodo-2-(methylsulfonyl)-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.

To a suspension of 6-chloro-5-iodo-2-(methylsulfonyl)-lH-benzo[d]imidazole (5.042 g, 14.14 mmol) in DCM (100 mL) at 0C 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 0C 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 Na2S04, concentrated and the residue was purified on silica gel column using EtOAc/hexane as eluting solvents to give the title compound. LC/MS: (M+l) : 487.17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

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; WO2015/112441; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, 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. category: imidazoles-derivatives

(b) 5-Bromo-lH-imidazole[00356] 2,4,5-Tribromo-lH-imidazole (32 g , 0.105 mol) was refluxed with 20% aqueous sodium sulphite solution (66.34 g, 0.527 mol) for 8 h. The solid product precipitated upon cooling and was collected by vacuum filtration to yield 12.5 g of the desired product. LC-MS: 147, 149 (M+H+).

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emerson; HEWITT, Michael, Charles; JONES, Philip; XIE, Linghong; WO2011/150156; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 87941-55-7, The chemical industry reduces the impact on the environment during synthesis 87941-55-7, name is 4-Bromo-1-trityl-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a single-necked flask was added 4-bromo-1-trityl-1H-imidazole (1.5 g, 3.9 mmol)Sodium carbonate (1.2 g, 11.7 mmol),2-formylbenzeneboronic acid (864 mg, 5.8 mmol) and DMF (10 ml)Water (2 ml), the reaction system was filled with nitrogen,Tetrakis (triphenylphosphine) palladium (242 mg, 0.195 mmol) was added under nitrogen,90 C for 16 h, add water,Ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate, the solvent was concentrated,Purification by column chromatography on silica gel afforded compound 8 (930 mg, yield 58%).

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, 4-Bromo-1-trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 15813-09-9, 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. 15813-09-9 name is 4,5-Diiodo-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.

Step b: 4-(4-iodo- lH-imidazol-5-yl)tetrahydro-2H-pyran-4-ol[0548] ft-BuLi (2.5 M, 24.8 mL, 62.0 mmol) was added to a solution of 4,5-diiodo-lH-imidazole (9.6 g, 30.0 mmol) in THF (100.0 mL) at -78C and the mixture was stirred at -78C for 30 min. Dihydro-2H-pyran-4(3H)-one (6.0 g, 60.0 mmol) was added and the reaction mixture was stirred at -78C for 10 min and then allowed to warm to room temperature over 1 h. Saturated NH4C1 solution was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE to PE/EA = 1 : 1 to DCM/MeOH = 50: 1) to give 2.7 g of the title compound as a white solid (30%> yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Diiodo-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ZENOBIA THERAPEUTICS, INC.; BOUNAUD, Pierre-Yves; NIENABER, Vicki; STEENSMA, Ruo, W.; LOWE, John, A., III; WO2012/178015; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, A common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

B. 1-(1-Trityl-1H-imidazol-4-yl)ethanol (cas No.62256-50-2) To 1-trityl-4-carboxaldehyde-1H-imidazole (11.7 g, 34.6 mmol) in THF (250 ml) at 0 C. is added methylmagnesium bromide (12.6 mL, 38 mmol, 3.0 M in diethyl ether). The reaction mixture is stirred at 15 C. for 4 h before quenching with water (10 mL), followed by aqueous ammonium chloride. The reaction is extracted into ethyl acetate and washed with 30 mL of saturated aqueous sodium bicarbonate. The organic solvent is removed in vacuo. Chromatography (silica gel, ethyl acetate:hexanes, 1:1 to 1:0) yields the desired product. MS (ESI) m/z 355 (M+H). (prepared similarly in J. Med. Chem. 1977, 20(5), 721)

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ksander, Gary Michael; Meredith, Erik; Monovich, Lauren G.; Papillon, Julien; Firooznia, Fariborz; Hu, Qi-Ying; US2007/49616; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 103057-10-9, name is 4-(Chloromethyl)-1-trityl-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 103057-10-9, COA of Formula: C23H19ClN2

Example 8 Preparation of bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate: To a solution of bis(2,2,2-trifluoroethyl)phosphite (0.11 ml, 0.6 mmol) in THF (1.5 ml) were added 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (0.09 ml, 0.6 mmol) and (1-triphenylmethylimidazol-4-yl)methyl chloride (71.8 mg, 0.2 mmol). The reaction mixture was refluxed under argon flow for 22 hours. The solvent was removed under reduced pressure, and water (10 ml) was added to the residue, which was then extracted 3 times with ethyl acetate (10 ml). The resultant organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained white solid was purified through chromatography on silica gel column using ethyl acetate – hexane (3:2) to give bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate (34 mg, 30%) as a white powder. This powder was recrystallized from a mixture of ethyl acetate and hexane to provide a white small needle crystal (m.p. 145-148C). 1H NMR (CDCl3) d 3.34 (d, J = 10.5 Hz, 2H), 4.30 (quint, d, J = 3.9 Hz, 1.3 Hz, 4H), 6.80 (s, 1H), 7.08-7.50 (m, 16H). 31P NMR(CDCl3) d 29.9 (s). Anal Calcd for C27H23N2O3PF6: C, 57.03; H, 4.08; N, 4.93. Found: C, 57.03; H, 4.19; N, 4.94.

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; Azwell Inc.; EP1477487; (2004); 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Trityl-1H-imidazole-4-carbaldehyde

Under argon atmosphere, 8.5 ML (4.43 mmol, 1.5 equivalents) of the solution of tert-butyl bromozincacetate in tetrahydrofuran obtained in Example 59 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-5-carbaldehyde in 10 ML of THF at 5?9C. The mixture was stirred at 2?5C for 3 hours and 30 minutes. 10 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 15 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 5 ML of 1N hydrochloric acid, 5 ML of water, 5 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 5 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. Concentration under reduced pressure, the residue was loosened with 7 ML of IPE, filtered and washed with 7 ML of IPE. After washing, vacuum drying (40C) to a constant weight afforded 1.15 g of the desired product (yield 86%).1H NMR (CDCl3): delta 1. 4 2 (9H, s), 2.70-2.85 (2H, m), 3.52 (1H, d, J=4.8 Hz), 5.03-5.09 (1H, m), 6.79 (1H, s), 7.09-7.15 (6H, m), 7.30-7.38 (10H, m).

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 33016-47-6.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1471056; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application 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.

To a solution of 6-chloro- 5 -iodo-2-methanesulfonyl-l H-benzoimidazole (1.53g, 4.3 mmol) in DMF (21 ml) at 0C was added sodium hydride (60% dispersion in mineral oil, 190 mg, 4.7 mmol). After 15 minutes, the reaction was warmed to rt and stirred for 1 hour. The mixture was then cooled to 0 0C and 4-bromomethyl-birhohenyl (1.2 g, 4.7 mmol) was slowly added. The mixture was then warmed to rt and stirred overnight. The volatiles were removed on a rotary evaporator and the residue was partitioned between EtOAc and half-saturated ammonium chloride. The aqueous layer was extracted a second time and the organic extracts were combined. The combined EtOAc extracts were washed with H2O5 brine, and then dried with MgSO4. The crude oil obtained upon rotary evaporation was triturated in Et2O and filtered to yield the title compound as a beige solid.

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.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); 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 152628-02-9 as follows. HPLC of Formula: C19H20N4

4-Methyl-6-(l -methyl benzimidazol-2-yl)-2-n-propyl lH-benzimidazole (50gms) is suspended in acetone (500 ml), aqueous potassium hydroxide solution (13.8 gms in 31.4 ml of water) is added and mixed for 30 min at temperature of 25 – 3O0C. The mass is cooled, t-Butyl 4″-(bromomethyl)-2-biphenyl-2-carboxylate (50 gms) slowly added over 30 min and maintained the reaction mass at temperature of 0 – 50C for 6 hrs. The solvent is distilled off from the reaction mass at temperature below 5O0C under vacuum. Water (500 ml), Methylene chloride (300 ml) is added to the residue and mixed for about 15 min. pH of the reaction mass is adjusted with hydrochloric acid to 1.8 at temperature of 20 – 250C. Reaction mass is allowed to settle, layers are separated, aqueous layer is extracted with methylene chloride (100 ml). Combined organic layer is washed water (100 ml), treated with charcoal (5 gms) and dried the organic layer over anhydrous sodium sulphate (10 gms). Solvent is distilled off from the dried organic layer at EPO temperature below 50upsilonC finally under vacuum. Acetone (100 ml) is added to the residue,* mixed for about 10 min and solvent is distilled off under vacuum at temperature below5O0C. Acetone (300 ml) is added to the residue, cooled the mass to 3O0C and pH of the mass is adjusted to 2.8 with IPA HCl (about 2 ml). Temperature of reaction mass is raised, maintained for 1 lir at reflux temperature, cooled and maintained for 30 min at 25- 3O0C. Product is filtered, wet cake is washed with acetone (50 ml) and dried the wet cake at temperature of 60 – 7O0C till becomes constant weight.The Dry weight of tert Butyl 4Lambda-[4-Methyl-6-(l-methyl-lH-benzimidazol-2-yl)-2-n- propyl- lH-benzimidazol-l-yl-methyl]biphenyl-2-carboxylate hydrochloride is 73 gms (Yield: 73%). HCl content: 5.85 % w/w

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MATRIX LABORATORIES LIMITED; WO2007/10558; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem