Category: imidazoles-derivatives

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. 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

Step 1: 4-(6-bromo-2-(2-(difIuoromethyl)-lH-benzo[d]imidazol-l-yl)-8-methoxyquinazoHn-4-yl)morpholineTo a stirred mixture of 4-(6-bromo-2-chloro-8-methoxyquinazolin-4-yl)morpholine (300 mg, 0.00084 mol) and potassium carbonate (348 mg, 0.00251 mol) in N,N-dimethylformamide ( 10 ml) was added 2-(difluoromethyl)-lH-benzo[d] imidazole (169 mg, 0.001 mol) at room temperature. The reaction mixture was heated at 80C for 16 h. The reaction mixture was added to ice-cold water ( 100 mL). The solid separated was collected by filtration, washed with 5% EtOAc in hexane and dried under vacuum to afford the title compound as white solid (230 mg, 56%). H NMR (400 MHz, DMSO-d6) : delta 8.67 (d, J = 8.40 Hz, 1 H), 7.96 (t, J = 53.2 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.54 (d, J = 2.0 Hz, 1H), 7.53-7.43 (m, 2H), 4.05 (s, 3H), 3.94-3.83 (m, 8H); ESI-MS : Calculated mass: 489.06; Observed mass: 490.20 [M + H]+.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 827-43-0, 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. 827-43-0 name is 4-Methyl-2-phenyl-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.

Into a 15mL pressure tube, sequentially add 1o (47.5mg, 0.3mmol), dichloromethane (3mL), 2a (84.7mg, 0.45mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3o (67.2 mg, 65%) as a white solid product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-phenyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5955-72-6, 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. 5955-72-6 name is 2-Chloro-6-nitro-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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil.

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

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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 2466-76-4, Formula: C5H6N2O

General procedure: To a solution of N -acetylimidazole 7a (1 mmol) and a suitable Baylis-Hillman acetate 1 (1 mmol) in DMF (1 mL), K2CO3 (1 mmol) was added and the resulting mixture was stirred at room temperature until complete consumption of N -acetylimidazole 7a. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SO4 . After removal of the solvent under reduced pressure, the residue was puried by flash chromatography over silica gel with EtOAc and hexane (1:1). (E)-Methyl 2-((1-imidazolyl)methyl)-3-phenylacrylate (8a) Yellow oil; yield (141 mg, 58percent); 1H NMR (500 MHz, CDCl3) : 8.03 (s, 1H), 7.48 (s, 1H), 7.42 (d, J =7.4 Hz, 3H), 7.31 (d, J = 6.8 Hz, 2H), 7.01 (s, 1H), 6.85 (s, 1H), 4.96 (s, 2H), 3.79 (s, 3H); 13C NMR (125MHz, CDCl3) : 166.9, 144.9, 137.0, 133.9, 129.7, 129.1, 129.0, 128.8, 127.0, 118.8, 52.5, 43.0; HRMS (IT-TOF); Anal. Calcd. for C14H14N2O2 : m=z 243.1128; Found [M+H]+: m=z 243.1126.

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

Reference:
Article; Koeseceli Oezenc, Ay?en; Celik, Ilhami; Koekten, ?ule; Turkish Journal of Chemistry; vol. 41; 3; (2017); p. 323 – 334;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H8N2

General procedure: A sealable reaction tube equipped with a magnetic stirrer barwas charged with 5,6-dimethyl-1H-benzo[d]imidazole (0.50 mmol,73 mg), benzaldehyde (1.0 mmol, 106 mg), di-tert-butyl-peroxide(1.0 mmol, 146 mg), 4 A molecular sieves (50 mg) and ethyl acetate(3.0 mL). The rubber septum was then replaced by a Teflon-coatedscrew cap, then the reaction must be under N2 and the reactionvessel placed in an oil bath at 110 C. After stirring the mixture atthis temperature for 15 h, it was cooled to room temperature anddiluted with ethyl acetate then washed with 0.5 mmol/L NaOHaqueous solution (5.0 mL3), dried over by MgSO4. After the solventwas removed under reduced pressure, the residue was purifiedby column chromatography on silica gel (hexane/EtOAc, 4:1 to6:1) to afford the desired product (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone (3a, 116 mg, 93% yield).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Lin; Wang, Min; Wang, Lei; Tetrahedron; vol. 70; 35; (2014); p. 5391 – 5397;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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: 10 mL ethanol solution of 2.0 mmol metal salt was added into 10 mL ethanol solution of 2.0 mmol 4,5-imidazole dicarboxylic acid. Having blended the mixture under reflux for 1 h, methanol solution of 1.0 mmol NaOH was put into hot mixture drop by drop. After 5 h under reflux, solvent of the solution was removed, precipitate was filtered. The precipitates were washed with methanol 3 times and dried in 105 C. Molecular structures of complexes obtained from the reaction of 4,5-imidazole dicarboxylic acid ligand with metal salts were summarized in Fig. 2.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Article; Erdem, Ozlem; Yildiz, Emel; Inorganica Chimica Acta; vol. 438; (2015); p. 1 – 4;,
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 288-32-4 as follows. Formula: C3H4N2

General procedure: Briefly, a mixture of imidazole (100 mmol), alkyl bromide (100 mmol) and K2CO3 (200 mmol) inacetone (200 mL) was refluxed overnight. Upon filtration and solvent removal, the remaining residuewas subjected to flash chromatography with ethyl acetate to produce >90percent yield.

According to the analysis of related databases, 288-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Doria, Oscar Forero; Castro, Ricardo; Gutierrez, Margarita; Valenzuela, Diego Gonzalez; Santos, Leonardo; Ramirez, David; Guzman, Luis; Molecules; vol. 23; 9; (2018);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 25676-75-9, 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 25676-75-9 as follows.

Step 1: A solution of 4-bromo-1-methyl-1H-imidazole (1.0 g, 6.2 mmol), (4-fluoro-3-methylphenyl)boronic acid (1.0 g, 6.5 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.6 g, 0.52 mmol) and aqueous Na2CO3 (2 M, 4 mL, 8.0 mmol) in a mixture of DME/EtOH/H2O (7:3:2, 10 mL) was evacuated and then refilled with nitrogen (three cycles). Resulting reaction mixture was then irradiated in the microwave at 150 C. for 50 min., dried (MgSO4), filtered and concentrated under reduced pressure to give a black residue, which was purified by column chromatography eluting with MeOH/DCM to provide 4-(4-fluoro-3-methylphenyl)-1-methyl-1H-imidazole (0.6 g, 51%). MS m/e: 191 (M+H)+.

According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; Bristol-Myers Squibb Company; Kinsella, Todd; Gelman, Marina; Hong, Hui; Darwish, Ihab S.; Singh, Rajinder; Yu, Jiaxin; Borzilleri, Robert M.; Velaparthi, Upender; Liu, Peiying; Darne, Chetan; Rahaman, Hasibur; Warrier, Jayakumar Sankara; (311 pag.)US2016/257690; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1 name is 2-Chloro-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.

PREPARATION 2 (1-(4-Fluorobenzyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine Combine 2-chloro-1H-benzimidazole (17.75 g, 116 mmol) and 4-fluorobenzyl bromide (26.6 g, 141 mmol) in dimethylformamide (100 mL). Add a solution of sodium hydroxide (50 g) in water (75 mL). (Caution, exothermic). After 30 minutes, pour the reaction mixture into water (1800 mL) and stir to form a solid. After 1 hour, collect the solid by filtration, dissolve the solid in dichloromethane, and extract with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluding with 5% ethyl acetate/dichloromethane to give a solid. Recrystallize from chloroform/hexane to give, after drying, 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole.

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

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6211199; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 96797-15-8, These common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, 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.

To a solution OF 4-IODO-1-TRITYL-LH-IMIDAZOLE (25 g, 57.2 mmoles) in THF (150 ML) at room temperature was added ethylmagnesium bromide (69 ml, 68. 7 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (9.4 g, 68.6 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (6.6 g, 5.72 mmoles) and 5-BROMO-2-METHOXYPYRIDINE (8.9 ml, 68. 7 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane (500 ml) and washed with a 30% NaOH solution containing an added 20 g of EDTA (3x 200 ML), with NaCl (sat. ) (200 ml), dried over MGS04, filtered, and concentrated. To the crude material was added dichloromethane (200 ml) and trifluoroactetic acid (40 ml, 410 mmoles). After standing for 6 hours, the reaction was concentrated and pumped on overnight. The crude material was purified by flash chromatography using 0-5% MEOH/CH2CL2 with 0.1% triethylamine yielding 5-imidazol-4-yl-2-methoxypyridine (7. 0g, 70%). MH (176)

The synthetic route of 96797-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2004/96823; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem