Imidazoles-derivatives

4887-80-3, 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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: PhI(OAc)2 (0.5 mmol) was added to a mixture of 1H-benzimidazole(1a; 0.5 mmol), isochroman (2a; 2.0 mmol), and DCE (2.0mL) in a Schlenk tube at r.t. The mixture was stirred at 80 C for6 h then cooled. H2O (10 mL) was added, and the mixture wasextracted with CH2Cl2 (3 ¡Á 10 mL). The combined organic layerwas dried (Na2SO4) and concentrated under reduced pressure.The residues were purified by flash column chromatography(silica gel, hexane-EtOAc) to give a colorless oil; yield: 115 mg(92%).

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Reference:
Article; Sun, Bin; Yan, Zhiyang; Jin, Can; Su, Weike; Synlett; vol. 29; 18; (2018); p. 2432 – 2436;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below.

To a solution of N-H heterocycle (1 mmol) and aryl halide (2 mmol) in toluene were added catalyst (0.07 g, 0.016 mmol) and K2CO3 (276 g, 2 mmol) and the mixture stirred at 110 C for the specified time. The progress of the reaction was monitored by TLC. The reaction mixture allowed cooling to room temperature and ethyl acetate (25 mL) was added and the mixture stirred for 15 min to ensure product removal from catalyst. Then the catalyst was filtered, washed with ethyl acetate (2 9 25 mL). The organic layer was evaporated under vacuum on a rotary evaporator and the crude product was obtained. Further purification was achieved by column chromatography using ethyl acetate/n-hexane gradient. Structural assignments of the products are based on their 1H NMR and melting point.

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; Hosseinzadeh, Rahman; Aghili, Nora; Tajbakhsh, Mahmood; Catalysis Letters; vol. 146; 1; (2016); p. 193 – 203;,
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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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., 570-22-9

In a dried flask, to 1H-imidazole-4,5-dicarboxylic acid (25 g, 157 mmol) in toluene (334 ml), DMF (12.1 ml) and thionyl chloride (94 ml, 1.29 mol) were added. The mixture was stirred for24 h at 80G. The mixture was concentrated under reduced pressure. Toluene (100 ml) was added and the mixture was concentrated under reduced pressure to give 35.5 g of the title compound as crude material which was used at the same day without further purification for subsequent steps.

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; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
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Imidazole | C3H4N2 – PubChem

1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-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 1003-21-0.

5-Bromo-1-methyl-1H-imidazole (0.50mmol), Pd(PPh3)2Cl2 (0.025mmol, 5.0mol%), K2CO3 (1.0mmol, 2.0mol equivalent), DMF (2.0mL), distilled water (2.0mL) and the corresponding phenylboronic acid (0.60mmol), were added in a 10mL round bottom flask. The mixture was stirred at 90C for 24h. After completion of the reaction, the mixture was cooled down to room temperature and extracted 3 times with ethyl acetate. The combined ethyl acetate extract was dried using anhydrous MgSO4. The solvent was removed under reduced pressure and the product was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) followed by 7% methanol in ethyl acetate as an eluent.2.2.1 13 5-(4-Methoxyphenyl)-1-methyl-1H-imidazole (1) (0007) Yellow solid; isolated yield (83%); 1H NMR (500MHz, CDCl3) delta (ppm): 7.48 (s, 1H, C-H- arom), 7.30 (d, 2H, J=8.8Hz, C-H arom), 7.03 (s, 1H, C-H-arom), 6.96 (d, 2H, J=8.5Hz, C-H arom), 3.84 (s, 3H, CH3), 3.62 (s, 3H, CH3). 13C NMR (125MHz, CDCl3) delta (ppm): 32.20, 55.20, 114.03, 122.06, 127.39, 129.54, 129.78, 133.07, 138.47, 159.28 (C- arom); IR (v, cm-1): 3084, 2947, 1899, 1720, 1611, 1552,1491, 1234, 1116, 1023; GC-MS m/z: 188 (M+1). Anal. Calc. for C11H12N2O (188): C, 70.19; H, 6.43; N, 14.88. Found: C, 70.35; H, 6.83; N, 14.80.

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

Reference:
Article; Ibrahim, Mansur; Malik, Imran; Mansour, Waseem; Sharif, Muhammad; Fettouhi, Mohammed; El Ali, Bassam; Journal of Organometallic Chemistry; vol. 859; (2018); p. 44 – 51;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

35203-44-2, A common compound: 35203-44-2, name is 1-Propyl-1H-imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Weigh 184g of 1,3-propane sultone, and add 1L of ethyl acetate to the reactor, and install a constant pressure dropping funnel.Magnetic stirrer and reflux condenser, slowly add 123g N-propyl imidazole when heated to 60 ¡ã C in a water bath.After the completion of the dropwise addition, the system was kept at 80 ¡ã C for 2 h to produce a white precipitate;The system was subjected to vacuum filtration, and the cake was washed with ethyl acetate.It is dried in an oven at 100 ¡ã C, and the obtained product is 1-(3-sulfonate)propyl-3-propylimidazolium salt;The 1-(3-sulfonate)propyl-3-propylimidazolium salt is dissolved in water, and concentrated sulfuric acid is added to carry out the reaction at 85 ¡ã C.The water is then removed to give a pale yellow viscous liquid product which is the 1-propyl-3-propanesulfonic acid imidazolium hydrogensulfate ionic liquid.

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

Reference:
Patent; Hangzhou Geng Lan Biological Technology Co., Ltd.; Dong Qiuyue; Yang Caihua; (6 pag.)CN109053372; (2018); A;,
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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 26576-46-5 as follows. 26576-46-5

Formation of the dispersion synergist SYN-D was accomplished by diazotation of compound 6 and subsequent coupling with compound 3. according to the following synthesis scheme: [Show Image] 17.3 g (0.1 mol) of compound 6 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 98 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

22884-10-2, Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2.

To a 50 mL flask was added 4-trifluoromethyl-2-azidoaniline1c (1 mmol), alpha-bromotrifluoroacetone (1.2mmol) And potassium carbonate (1.5mmol), React at 45 C, The reaction solvent was chloroform (20 mL). After 2 hours of reaction, Additional diphenylmethylphosphine (1.5 mmol) was added. The reaction was carried out at 30 C, and after continuing the reaction for 3 hours, The solvent chloroform was removed under reduced pressure. The intermediate was transferred to a solution of triphenylphosphine (2.5 mmol) and elemental iodine (2.5 mmol) in chloroform (15 mL). Then add imidazoleacetic acid (1.5 mmol), React at 45 C, Reaction for 2 hours, After the reaction is completed, The solvent chloroform was removed under reduced pressure. The primary product was subjected to column chromatography to give 0.192 g of the title compound 2c, yield 51%.

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-(1H-Imidazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hubei Wenli College; He Ping; Wang Liping; Pei Fei; Jin Shan; Ren Zhilin; Wang Long; (10 pag.)CN109400589; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 139481-72-4, name is Trityl candesartan, molecular formula is C43H34N6O3, 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. 139481-72-4

Step I: Preparation of N-trityl candesartan cilexetilA mixture of N-trityl candesartan (Form A: 120 gm), potassium carbonate (48.58 gm), cilexetil chloride (54.48 gm) and dimethyl formamide (180 mL) at ambient temperature was heated to 60 C to 65 C followed by stirring at the same temperature for 2 hours and 30 minutes. The reaction mixture was cooled to 25 C to 30 C followed by addition of dichloromethane (600 mL) and ice cooled de-ionized water (1200 mL) at 10 C to 15 C to the reaction mass. The reaction was further stirred at 15 C to 20 C for 30 minutes followed by extraction of the aqueous layer with dichloromethane (120 mL) at 15 C to 30 C and washing with de-ionized water (2×600 mL) at ambient temperature.The organic layer was concentrated completely under vacuum at 30 C to 35 C followed by removal of traces of dichloromethane with cyclohexane (120 mL) and the further addition of cyclohexane (360 mL) to the residue at the ambient temperature. The reaction mixture was stirred at the same temperature for 14 hours followed by filtration and washing of the solid with cyclohexane (120 mL) which was suck dried under vacuum for 1 hour. Dichloromethane was again added (360 mL) at ambient temperature to the isolated solid followed by heating and stirring of the reaction mass at 30 C to 35 C for 30 minutes. The organic layer was concentrated under vacuum at 30 C to 35 C, cyclohexane (300 mL) added and the reaction mass was stirred further for 5 hours at the same temperature. The solid was filtered, washed with cyclohexane (120 mL) and suck dried under vacuum for 1 hour followed by further drying under vacuum for 16 hours at 35 C to 40 C.Chromatographic purity: 98.8%N-trityl desethylcandesartan cilexetil- 0.28%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 139481-72-4, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; SANJEEVI, Lakshmipathi V.; ALLADA, Suresh; KUMAR, Ashok; SINGH, Kaptan; GUNTU, Srinivasa Rao; WO2011/92666; (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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., 33543-78-1

To a stirred solution of hydroxylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H20 (17 mL) at 0 C, ethyl lH-imidazole-2-carboxylate (11.0 g, 78.6 mmol, 1.0 eq) was added and the resulting mixture was stirred at 90 C for 30 min. The mixture was cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) was added in portions. The resulting mixture was stirred at RT overnight, filtered and rinsed with H20 (10 mL x 3). The filtrate was extracted with ethyl acetate (50 mL x 5). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (1% MeOH in DCM) to afford ethyl 1 -amino- lH-imidazole-2-carboxylate (800 mg, 6.5 % yield). ESI-MS m/z: 156.1 [M+H]+.

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; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); 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. 583-39-1, name is 2-Mercaptobenzimidazole, A new synthetic method of this compound is introduced below., 583-39-1

General procedure: To an orange suspension of [Pd2(kappa2:C, N-mazb)2(mu-Cl)2] (0.025g, 0.040mmol) in dichloromethane (5mL), N-methylimidazolidine-2-thione (0.012g, 0.080mmol) was added in presence of Et3N base (0.5mL). The color of the reaction mixture became red brown and was stirred for 5-6h. The solution was filtered and methanol (5mL) was added and was left to evaporate slowly. The red brown crystals of compound 7 were obtained after a period of 4-5d.

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; Sandhu, Amanpreet K.; Lobana, Tarlok S.; Sran, Balkaran S.; Hundal, Geeta; Jasinski, Jerry P.; Journal of Organometallic Chemistry; vol. 861; (2018); p. 112 – 124;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem