Category: imidazoles-derivatives

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

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

Electric Literature of 16681-59-7,Some common heterocyclic compound, 16681-59-7, name is 2-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.

Example 40 N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-1 -(1 -methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (E40) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); To a stirred mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4- imidazolidinecarboxamide (91 mg, 0.3 mmol) (prepared as described in Example 28) and 2-bromo-1 -methyl-1 H-imidazole (48.3 mg, 0.3 mmol) in 1 ,4-dioxane (6 ml) was added potassium phosphate (318 mg, 1.5 mmol), copper (I) iodide (57.1 mg, 0.3 mmol) and trans-N,N-dimethylcyclohexane-1 ,2-diamine (0.047 ml, 0.3 mmol) and the mixture was heated at reflux under argon for 3 hours. The mixture was cooled to room temperature and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(1- methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (22 mg, 19%). LC/MS [M+H]+ = 384, retention time = 1.69 minutes.

The synthetic route of 16681-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15965-31-8, 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. 15965-31-8, name is 5-Chloro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-chloro-l-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone (550 mg; 1.74 mmol) and 4- chloroimidazole (214 mg; 2.09 mmol; 1.20 eq) in dry acetonitrile (5.0 mL) was stirred at 80C for 20 h, then at 130C for 1 h under microwave irradiation. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with water, the organic layer was washed with saturated aqueous sodium bicarbonate, dried (MgSO i) and concentrated to dryness in vacuo. The oily residue was purified by chromatography over silica gel, eluted with a mixture of w-heptane/ethyl acetate (100:0 to 0: 100). After evaporation of the solvents, a second purification by preparative HPLC was performed. Evaporation of the solvents in vacuo afforded 141 mg (21%) of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5-chloroimidazol- l-yl)ethanone as a colourless solid. MS (ESI): 381.0 ([M+H]+)

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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 152628-02-9, Recommanded Product: 152628-02-9

The double-benzimidazole heterocyclic compound (500 mg, 1 . 64mmol) soluble in 20mLN, in N – dimethyl formamide, adding sodium hydrogen (79 mg, 3 . 3mmol) at room temperature under stirring 30min, slow the instillment contains N – O-cyano phenyl -4 – bromo methyl indole (560 mg, 1 . 8mmol) of N, N – dimethyl formamide solution (10 ml) in. The mixed liquid continuing stirring at room temperature instead on invitation 2h, TLC monitoring to the reaction is complete. Filtering, the filter cake is dichloromethane (10 ml ¡Á 3) washing three times. In the filtrate by adding 200 ml of methylene chloride and 200 ml water, takes organically. After the dichloromethane (150 ml ¡Á 3) extracting the aqueous phase three times, the combined organic phase. For saturated salt water (300 ml ¡Á 4) washing the organic phase four. For drying the organic phase with anhydrous magnesium sulfate, filter, evaporate the solvent under reduced pressure, to obtain amber solid. The solid weight crystallized to obtain gray solid about 600 mg (yield is about 68.3%).

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, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chen, Zhilong; Zhu, Weibo; Ren, He; Yan, Yijia; Bao, Xiaolu; Chen, Danye; (16 pag.)CN106467521; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8,Some common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, molecular formula is C5H3F3N2O, 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.

5-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (Step 4) To a stirred solution of hexamethyldisilazane (2.5 ml, 11.75 mmol) in tetrahydrofuran (25 ml) was added n-butyllithium (7.5 ml, 11.75 mmol) dropwise at 0 C. under nitrogen. The reaction mixture was stirred at room temperature for 30 min. Then cooled to -78 C., to the mixture was added a solution of 1-(4-bromo-3-fluorophenyl)-1-butanone (2.4 g, 9.79 mmol) in tetrahydrofuran (12 ml) dropwise and stirred at rt for 1 h. Then 1-trifluoroacetylimidazole (1.3 ml, 11.75 mmol) was added to the mixture at same temperature, the mixture was stirred at rt for 5 h. This was quenched by water and the pH was adjusted to pH 4-5, extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:20/1:15) to afford 2.7 g (80.9%) as a yellow oil. A mixture of 1-(4-bromo-3-fluorophenyl)-2-ethyl-4,4,4-trifluoro-1,3-butanedione (1.5 g, 4.40 mmol) and 5-hydrazino-2-pyridinesulfonamide hydrochloride (1.28 g, 5.72 mmol) in ethanol (60 ml) was stirred at reflux for 3 h. After cooling, the solvent was removed and the residue was diluted with ethyl acetate, washed with water. The extracts was dried (MgSO4), and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:10/1:5/1:4) to afford 1.64 g (75.6%) of the titled compound as a white amorphous. 1H-NMR (CDCl3) delta: 8.58-8.57 (1H, m), 7.99-7.95 (1H, m), 7.79 (1H, dd, J=8.6, 2.5 Hz), 7.70-7.64 (1H, m), 7.05 (1H, dd, J=8.6, 1.8 Hz), 6.91-6.88 (1H, m), 5.40 (2H, br.s), 2.56 (2H, q, J=7.6H), 1.14 (3H, t, J=7.6 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, its application will become more common.

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); 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 71759-87-0 as follows. category: imidazoles-derivatives

Example 54: 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1-methyl-1H-imidazol-4-yl)-1 H-pyrrolo[2,3-b]pyridine[340] To a stirred mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5- tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (10.0 mg, 0.0229 mmol), 4-iodo- 1-methyl-1H-imidazole (7.17 mg, 0.0344 mmol), potassium carbonate (9.53 mg, 0.0689 mmol) in DME (2.0 ml.) and H2O (0.40 ml.) was added (1 ,1′-bis-(diphenylphosphino)ferrocene) palladium dichloride (0.84 mg, 0.001 1 mmol) under nitrogen atmosphere. The resulting mixture was refluxed at 100 C for 90 min. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (eluent: 2% MeOH in DCM) to give desired product. 1H NMR (400 MHz, CD3OD): delta = 1.88 (d, J = 7.1 Hz, 3 H), 3.75 (s, 3 H), 5.30 (q, J = 6.8 Hz, 1 H), 7.12-7.18 (m, 1 H), 7.22 (d, J = 1.5 Hz, 1 H), 7.33 (d, J = 1.3 Hz, 1 H), 7.39 (br. s., 1 H), 7.62 (s, 1 H), 7.67 (d, J = 2.0 Hz, 1 H), 8.48 (d, J = 2.0 Hz, 1 H). MS (ES+): m/z 389.05 [MH+]. HPLC: tR =2.54 min (ZQ3, polar_5 min)

According to the analysis of related databases, 71759-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 152628-02-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3: Alkylation of (2-(1-propyl)-4-methyl-6-(1′-methylbenzimidazole-2-il)benzimidazole); [Show Image] 15 mL of sulfolane (tetramethylene sulfone) is charged to the flask. 0.85 g of PMB (2-(1-propyl)-4-methyl-6-(1′-methylbenzimidazole-2-il)benzimidazole) and 0.38 g of potassium tert-butoxide are added. The mixture is heated above 30 C to dissolve all the components. The solution is than cooled down to 15 C and 1.07 g of 4′-bromomethyl-2-iodo-biphenyl in 5 mL of solvent is added slowly during 45 minutes. The reaction mixture is stirred at the same temperature for additional 2 hours. 40 mL of demineralised water and 35 mL of EtOAc (ethyl acetate) are added. The phases are separated. The upper EtOAc phase is washed several times with saturated water solution of NaCl. The solvent is evaporated and 4 mL mixture of EtOAc and acetone is added. The suspension is stirred for 30 minutes at room temperature. The suspension is filtered and 0.94 g of white crystals of 3′-(2′-iodo-biphenyl-4-ylmethyl)-1,7′-dimethyl-2′-propyl-1 H,3’H-[2,5′]bibenzimidazolyl are obtained. 1H NMR (300 MHz, CDCl3) delta: 1.06 (t, J = 7.4 Hz, 3H), 1.84 – 1.92 (m, 2H), 2.95 (t, J = 7.8 Hz, 2H), 3.81 (s, 3H), 5.46 (s, 2H), 7.03 (ddd, J = 7.9 Hz, J = 7.4 Hz, J = 1.8 Hz, 1H), 7.13 (d, J = 8.0 Hz, 2H), 7.23 – 7.54 (m, 9H), 7.77 – 7.83 (m, 1H), 7.94 (dd, J = 7.9 Hz, J = 1.1 Hz, 1H).

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lek Pharmaceuticals D.D.; EP2103588; (2009); 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. 1072-63-5, name is 1-Vinyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H6N2

General procedure: 5 mmol of 1-vinylimidazole, 5 mmol of ethyl bromide were added to 30 mL of methanol in a 100 mL roundbottom flask at 0C. The mixture was stirred at room temperature overnight, followed by 60C for 15 h. After cooling down, the reaction mixture was added dropwise into 250 mL of diethyl ether and a white precipitate was formed. The precipitate was filtered off and washed with diethyl ether again and dried at room temperature until constant weight. (1H NMR, CDCl3, d ppm): 1.66 (t, 3H), 4.53(q, 2H), 5.42 (d, 1H), 6.00 (d, 1H), 7.48 (dd, 1H), 7.70 (s, 1H),7.87 (s, 1H), 10.97 (s, 1H).

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 1072-63-5.

Reference:
Article; Pourjavadi, Ali; Hosseini, Seyed Hassan; AghayeeMeibody, Seyyed Alireza; Hosseini, Seyedeh Talieh; Comptes Rendus Chimie; vol. 16; 10; (2013); p. 906 – 911;,
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