Author: Jessica.F

583-39-1, 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

Benzimid-azole-2-thione 1 (1.50 g, 10 mmol) and morpholine (0.87 ml, 0.87 g, 10 mmol) were dissolved in 2-PrOH (30 ml); 37% aqueous formaldehyde (0.90 ml, 12 mmol) was added, and the mixture was refluxed for 3 h (precipitate formed almost immediately). Th

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; Bespalov; Gorchakova; Ivanov; Kuznetsov; Kuznetsova; Pankova; Prokopenko; Avdontceva; Chemistry of Heterocyclic Compounds; vol. 50; 11; (2015); p. 1547 – 1558;,
Author Jessica.FPosted on November 18, 2020Categories 583-39-1, imidazoles-derivativesTags M.W=100-200

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

A 2 M isopropylmagnesium chloride solution in THF (8.60 mL, 17.2 mmol) was added dropwise to a solution of 4-iodo-1-trityl-imidazole (5.00 g, 11.5 mmol) in anhydrous THF (55 mL) at 0 C under nitrogen. The resulting mixture was stirred at 0 C for 10 minute

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; REDX PHARMA PLC; ARMER, Richard; BINGHAM, Matilda; PESNOT, Thomas; (84 pag.)WO2016/59412; (2016); A1;,

These common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity,

Add 1-methyl-2-mercaptoimidazole (0.23 g, 2.04 mmol) to a 150 mL round bottom flask with potassium carbonate as the base(0.32g, 2.35mmol), acetonitrile was stirred at 70 C for 30 minutes, then cooled to room temperature and then added to compound III.(0.

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 60-56-0.

A common heterocyclic compound, 2302-30-9, name is 4,5-Dibromo-1H-imidazole, molecular formula is C3H2Br2N2, 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. 2302-30-9.

(2) The product of the previous step (4-iodo-1H-imidazole and a little diiodo-substituted imidazole, 78 kg)60 kg of isopropyl alcohol and 240 kg of water were added,Adding 67.5 kg of sodium sulfite,Reflux reaction to raw material disappears.Cooled and filtered (the filtrate used as solvent in the next batch, no emissions)Extraction (using ethyl acetate extraction),Concentration under reduced pressure gave the compound 4-iodo-1H-imidazole (38 kg, purity was 99.2% by high performance liquid phase).

The synthetic route of 4,5-Dibromo-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Lide Biological Technology Co., Ltd.; Ren Guobao; Wu Yan; Li Chuanbin; (5 pag.)CN106674121; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0 C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; (53 pag.)US2017/258782; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); Ethyl imidazole-2-carboxylate (140mg, 1. Ommol), 4-formylbenzeneboronic acid (300mg, 2.0mmo.) and catalyst [Copper(OH).TMEDA] 2CI2 (46mg, 0.1 Ommol) were dissolved in 1 ,2-dichloroethane (5ml) and heated to 60¡ãC under an O2 atmosphere for 2Oh. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152mg). deltaH (CDCI3, 250MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1 H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/7018; (2007); 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 2302-25-2 as follows. 2302-25-2

To a solution of 4-bromo-7H-imidazole (lg, 6.80 mmol) in DMF (20 ml) was added NaH (0.272 g, 6.80 mmol) at 0 C. The mixture was stirred for 10 minutes, tert-butyl (3- bromopropyl)carbamate (1.62 g, 6.80 mmol) was added. The solution was stirred at room temperature for 2 hours and then heated at 50C for 1 hour. The mixture was quenched with water (50 ml) and extracted with EtOAc (3×20 ml). The organic layer was washed with water (30mL), brine (30mL) and dried over Na2SC”4. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (Redi 40g gold column), and eluted with EtOAc/Hexane (0-100%, 6cv; 100%, lOcv) to give the title compound. LC-MS [M + H]+: m/z 304.19. 1HNMR (500 MHz, CDC13) delta 7.40 (s, 1 H); 6.94 (s, 1 H); 4.67 (s, 1 H); 3.98 (t, J = 7.0 Hz, 2 H); 3.17 (d, J = 7.5 Hz, 2 H); 1.98 (p, J = 6.8 Hz, 2 H); 1.47 (s, 9 H).

According to the analysis of related databases, 2302-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; LIU, Weiguo; DING, Fa-Xiang; SUN, Wanying; ZANG, Yi; PAN, Weidong; OGAWA, Anthony; BROCKUNIER, Linda; HUANG, Xianhai; WANG, Hongwu; MAL, Rudrajit; BIFTU, Tesfaye; PARK, Min; GUO, Yan; JIANG, Jinlong; CHEN, Helen; PLUMMER, Christopher, W.; (258 pag.)WO2017/106064; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, molecular formula is C10H8N2O, 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. 10364-94-0.

General procedure: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.

The synthetic route of (1H-Imidazol-1-yl)(phenyl)methanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik; Tetrahedron Letters; vol. 53; 19; (2012); p. 2373 – 2376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

11. 4-(2-Propylimidazol-1-yl)benzyl alcohol Prepared from 2-propylimidazol and ethyl 4-fluorobenzoate. MW: 216.29 1 H NMR (CDCl3) delta: 7.60-7.80(m, 6H), 4.80(s, 2H), 2.70-2.45 (m, 2H), 2.00-1.50(m, 3H), 1.00-0.70(m, 3H).

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

Reference:
Patent; Pfizer Inc.; US5753682; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 288-32-4, name is 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. 288-32-4

Imidazole (200 g) was dissolved in tetrahydrofuran (600 ml). Jacketed reactor (4 L) was flushed with nitrogen and tetrahydrofuran (1 060 ml) was added. Potassium t-butoxide (339.9 g) was added through a funnel. The funnel and walls of the reactor were rinsed with tetrahydrofuran (140 ml). Content of the reactor was stirred for 15 minutes, cooled down to 0C and the imidazole solution was slowly added. Temperature of the reaction mixture was adjusted to 7C and methyl chloroacetate (302.9 g) was slowly added. The reaction mixture was stirred at 20-25C for 2 hours. Formed solid inorganic salts were filtered; the filter cake was washed with tetrahydrofuran (1 x 300 ml and 1 x 150 ml). Combined filtrates (approx. 1 800 ml) were transferred to clean jacketed reactor and water (300 ml) was added. The reaction mixture was heated under stirring to start distillation. Approx. 1 800 ml of volatile solvents were distilled off. The reaction mixture was stirred at 88-98C for additional 1.5 hr. The reaction mixture was then slowly cooled down to 25C. In the course of cooling, when the temperature of the reaction mixture reached 50C, methanol (1 050 ml) was added while continuing cooling. When the temperature of reaction mixture reached 25C, pH of the crystalline suspension was adjusted to 4-5 by addition of 36% hydrochloric acid (approx. 45 ml). Suspension was cooled down to 0C and stirred at -2 to 2C for 120 minutes. Product was then filtered, washed with methanol (500 ml) in several portions. Wet cake was dried at 60-65C for 10 hours to give 276.8 g of 2-(1H imidazol-1-yl)acetic acid. The product was analyzed by HPLC: content of diacid 0.07%, HPLC purity 99.22%.

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, 288-32-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Synthon B.V.; EP2192126; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem