Author: Jessica.F

Related Products of 934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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.

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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.

General procedure: A mixture of pyridine (1 mmol) in 3 mL dichloromethane was added dropwise to a magnetically stirred solution of 2-mercapto-1-methylimidazole or 5-mercapto-1-methyltetrazole (1 mmol) and acetylenic esters (1 mmol) in 15 mL dichloromethane. The reaction mixture was then stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane-ethyl acetate as eluent. The solvent was removed under reduced pressure to afford the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2(3H)-thione, its application will become more common.

Reference:
Article; Asgharian-Sheykhi, Fahimeh; Hassanabadi, Alireza; Akhgar, Mohammad Reza; Karbalaei-Harofteh, Mina; Khajehpour, Ehsan; Journal of Chemical Research; vol. 37; 9; (2013); p. 523 – 525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic 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 41716-18-1, Recommanded Product: 41716-18-1

[00393] To a solution of (+/?)-cis-N1-(2-chloro-7-methyl-7H-pyrrolo[2,3 -d]pyrimidin-4-yl)cyclohexane-i,3-diamine (110.5 mg, 9 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) was added N,N-diisopropylethylamine (0.16 mL, 1.19 mmol) and i-methyl-1H-imidazole-4-carboxylic acid (99 mg, 0.78 mmol). The mixture was stirred at rt for 10 minitues, and then HATU (300 mg, 0.79 mmol) was added. The resulting mixture was stirred at rt for 3 h. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a colorless solid (86 mg, 56percent).MS (ESI, pos.ion) m/z: 388.2 [M+H]+1H NMR (400 MHz, MeOD) (ppm) : 7.65 (d, J 6.1 Hz, 2H), 6.99 (d, J 3.3 Hz, 1H), 6.56 (d,J = 3.4 Hz, 1H), 3.78 (s, 3H), 3.72 (s, 3H), 2.68 (s, 2H), 2.34 (d, J = 11.6 Hz, 1H), 2.06 (s, 2H),1.93 (d, J = 13.6 Hz, 1H), 1.61 (d, J = 13.5 Hz, 1H), 1.44 (d, J = 11.7 Hz, 1H), 1.39 (d, J = 3.6Hz, 2H).

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 147403-65-4,Some common heterocyclic compound, 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, molecular formula is C25H24N4O4, 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.

Compound (3A) 9.5 g, placed in a reaction flask was added dichloromethane 100ml, 5ml of triethylamine was added dropwise 2.5 g of methyl chloroformate, the reaction at room temperature for 2 hours.Water was added to 60ml, stirring layers were separated dichloromethane layer was separated, and the aqueous layer extracted with dichloromethane, dichloromethane layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product was purified by solid 8.2, yield 79 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, its application will become more common.

Reference:
Patent; Shanghai Institute of pharmaceutical industry; Wang, Xiaomei; Sui, Qiang; Tang, Chao; Ouyang, Qunxiang; Shi, Huilin; Liu, Shuai; (18 pag.)CN103664920; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

To a solution of 2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidine-5-carboxylic acid (150 mg 0.366 mmol) 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (88 mg 0.366 mmol) and Et3N (55.6 mg 0.550 mmol) in 1 4-dioxane (10 mL) stirred under N2at 20 was added DPPA (121 mg 0.440 mmol) in one charge. The reaction mixture was stirred at 80 for 2 h. Then the solution was concentrated. The residue was purified by preparative TLC (DCM/MeOH 101 Rf 0.5) to yield a off white solid of 1- (2- (5-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-ethylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea (50 mg 0.077 mmol 21.07yield) . TLC (DCM/MeOH 101 Rf 0.4) 1HNMR(400 MHz CD3OD) delta9.07 (s 1H) 8.74-8.72 (m 1H) 8.12 (d J 9.3 Hz 2H) 7.98 (br. s. 1H) 7.77-7.75 (m 1H) 7.50 (br. s. 1H) 7.41 (d J 8.6 Hz 2H) 7.35 (s 1H) 6.92 (d J 8.8 Hz 2H) 5.40 (s 2H) 4.17 (d J 7.1 Hz 2H) 3.79 (s 3H) 2.91 (d J 7.5 Hz 2H) 2.26 (s 3H) 1.42 (td J 7.3 14.6 Hz 6H) ES-LCMS m/z 648.3 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, 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. 939-70-8 name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, 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 solution of 1-(1H-benzo [d] imidazol-2-yl)ethanone (2) (0.01 mol) in ethanol (60 ml),benzaldehyde (0.01 mol) and a few drops of glacialacetic acid were added and the mixture refluxed for10 hr. It was then cooled concentrated and pouredinto crushed ice and filtered. The solid thus obtainedwas purified by recrystallizaton from ethanol.1 H NMR (400 MHz, DMSO-d6): delta 6.81 (d, 1H,J=10.2 Hz), 6.98-7.20 (m, 5H), 7.24 (d, 1H, J=10.2Hz), 7.42 (m, 4H), 10.24 (brs, 1H). Mass [M+H], 249.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(1H-Benzo[d]imidazol-2-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Article; Bhaskar; Bharahmeswari; Indian Journal of Heterocyclic Chemistry; vol. 23; 2; (2013); p. 207 – 212;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 939-70-8,Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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.

General procedure: To a solution of 1-(1H-benzo [d] imidazol-2-yl)ethanone (2) (0.01 mol) in ethanol (60 ml),benzaldehyde (0.01 mol) and a few drops of glacialacetic acid were added and the mixture refluxed for10 hr. It was then cooled concentrated and pouredinto crushed ice and filtered. The solid thus obtainedwas purified by recrystallizaton from ethanol.

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

Reference:
Article; Bhaskar; Bharahmeswari; Indian Journal of Heterocyclic Chemistry; vol. 23; 2; (2013); p. 207 – 212;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 934-32-7, 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. 934-32-7 name is 1H-Benzo[d]imidazol-2-amine, 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.

General procedure: A mixture of 2-aminobenzimidazole 7 (1.33 g, 10.0 mmol), 10.0 mmol of the proper alkyl halide, 1.0 g of finely powdered KOH mixed with 2.0 g of anhydrous K2CO3 and acetone (50 mL) was heated at reflux for 3 h, with stirring. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and CH2Cl2 (100 mL), and the aqueous phase was further extracted twice with CH2Cl2. The combined extracts, dried over anhydrous Na2SO4, after removal of solvent afforded an oily or solid residue which was treated with a small amount of ethyl ether to give compounds 8a-e,l-o as whitish solids which were crystallized from the proper solvent. Only in the case of compound 8f, a preliminary purification by column chromatography [SiO2/ethyl acetate-acetone (1:1)] was necessary to obtain a crystalline compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Di Braccio, Mario; Grossi, Giancarlo; Signorello, Maria Grazia; Leoncini, Giuliana; Cichero, Elena; Fossa, Paola; Alfei, Silvana; Damonte, Gianluca; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 564 – 578;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16093-82-6, 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 16093-82-6 as follows.

Preparation 19-1) (2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine (21.5 g) and 2-carbamoylimidazole (7.07 g) were reacted in substantially the same manner as that of Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-{2-(2-carbamoylimidazol-1-yl) ethyl}-4-methylsulfonyloxypyrrolidine (15.2 g) as a yellow solid. NMR (CDCl3, 200 MHz, delta): 1.9-2.2 (2H, m), 2.4-2.6 (2H, m), 3.04 (3H, s), 3.5-3.7 (1H, m), 3.9-4.1 (2H, m), 4.5-4.6 (4H, m), 5.1-5.3 (3H, m), 5.63 (1H, br), 5.8-6.0 (1H, m), 7.0-7.3 (3H, m)

According to the analysis of related databases, 16093-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5608056; (1997); A;,
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 53710-78-4 as follows. HPLC of Formula: C6H9ClN2

EXAMPLE 23 A mixture of 4-(3′-chloro-4′-fluoroanilino)-6-hydroxy-7-methoxyquinazoline (1.5 g), 3-(imidazol-1-yl)propyl chloride (0.67 g), potassium carbonate (3 g) and DMF (40 ml) was stirred and heated to 90 C. for 1 hour. A second portion (0.12 g) of the propyl chloride was added and the mixture was heated to 90 C. for a further hour. The mixture was cooled to ambient temperature, filtered and evaporated. The residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained 4-(3′-chloro-4′-fluoroanilino)-6-(3-imidazol-1 -ylpropoxy)-7-methoxyquinazoline (0.66 g); NMR Spectrum: 2.5 (m, 2H), 4.12 (s, 3H), 4.25 (t, 2H), 4.35 (t, 2H), 7.08 (s, 1H), 7.4 (d, 2H), 7.6 (t, 1H), 7.8 (s, 1H), 7.95 (m, 2H), 8.25 (m, 1H), 8.65 (s, 1H), 9.7 (broad s, 1H); Elemental Analysis: Found C, 58.2; H, 4.6; N, 16.6; C21 H19 ClFN5 O2 0.2H2 O requires C, 58.5; H, 4.5; N, 16.2%.

According to the analysis of related databases, 53710-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; US5770599; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem