Month: July 2021

3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, 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: C14H19N3O2

Example-1 Preparation of Ethyl 4-{5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl}butanoate (III) Ethyl 4-[5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (II, 40.0 g, 0.153 mol) was added to 2-bromoethanol (80 mL) and agitated for 15-30 minutes. Acetonitrile (80 mL) and calcium carbonate (61.3 g, 0.61 mol) were added to the reaction mixture. The reaction mixture was heated to 80-90 C. within 2 hours and refluxed at 80-90 C. for 34-38 hours. The reaction mixture was cooled to below 70 C. and acetonitrile (80.0 mL) was added. The reaction mixture was further cooled to 20-30 C. and filtered through celite prewashed with acetonitrile. The filtrate was concentrated at 50-60 C. under vacuum till viscous mass is obtained. The viscous mass was cooled to 20-30 C. Dichloromethane (320.0 mL) was added to the viscous mass under stirring and washed with potassium carbonate solution (32.0 g in 200 mL water). The organic layer was washed with DM water twice. The organic layer (Dichloromethane) was concentrated under vacuum at 35-40 C. till viscous mass is attained. The viscous mass was dried under vacuum at 35-40 C. for one hour. Ethyl acetate (160.0 mL) was added to the viscous mass and cooled to 0-5 C. and stirred for one hour. The solid separated out was filtered and washed with ethyl acetate. The isolated solid was dissolved in dichloromethane and concentrated the solution under vacuum at 35-40 C. till viscous mass. The viscous mass was dissolved in acetone and cooled to 0-5 C. under stirring. The solid separated out was filtered, washed with acetone and dried at 40-45 C. under vacuum for 4-6 hours to give the title compound (III, 30.1 g; 56.30%), with a purity of 97.22%.

The synthetic route of 3543-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRESENIUS KABI ONCOLOGY LIMITED; MISHRA, Bhuwan Bhaskar; KACHHADIA, Nikunj Shambhubhai; TOMAR, Vinod Singh; LAHIRI, Saswata; US2014/121383; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-nitro-5-(phenylamino)phenol (KR-100061) (12.03 mmol, 2.77 g) in methanol (120 mL), PtO2 (0.60 mmol, 0.14 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for fifteen hours. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered quickly over a thin pad of celite which was then immediately washed with methanol (45 mL). The filtrate was concentrated in vacuo yielding an intense purple residue. The residue was quickly re-dissolved in acetonitrile (60 mL) and di(imidazole-1-yl)methanimine (30.08 mmol, 4.85 g) was added with constant magnetic stirring. The reaction was then placed under argon atmosphere and refluxed for six hours. The reaction was concentrated under reduced pressure and silica gel column chromatography (3:1 hexanes/ethyl acetate) provided a crystalline white solid in a 69% yield. The product of the reduction (2-amino-5-(phenylamino)phenol) is air unstable and appropriate measures should be taken to minimize air exposure.

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

Reference:
Article; Rynearson, Kevin D.; Charrette, Brian; Gabriel, Christopher; Moreno, Jesus; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3521 – 3525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6478-79-1, 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 6478-79-1 as follows.

To a solution of compound 1 (0.010?mol) in dry acetone, K2CO3 (0.025?mol) was added and the mixture was stirred at room temperature for 20?min. Then, methyl bromoacetate (0.011?mol) was added to the mixture and stirred at room temperature for one night. Afterwards, the reaction was completed (monitored by TLC, ethylacetate/hexane, 3:1). The product was precipitated by addition of water. It was filtrated off, and recrystallized from ethanol/water, 1:2. Yield: 92%, mp: 166-167?C. 1H NMR (DMSO-d6) ppm: 1.20 (3H, t, J?=?6.8?Hz, CH3), 2.44 (3H, s, CH3), 4.17 (2H. q, J?=?6.8?Hz, OCH2), 5.20 (2H, s, N-CH2), 7.78 (1H, s, Ar-H), 7.91 (1H, s, Ar-H). 13C NMR (DMSO-d6) ppm: 13.78, 14.42 (CH3), 45.12 (NCH2), 61.90 (OCH3), ArC:[112.25, 119.83, 124.45, 124.64, 135.65, 142.19], 155.72 (C=N), 168.35 (C=O). Anal. calcd. (%) for C12H12Cl2N2O2: C, 50.20; H, 4.21; N, 9.76. Found: C, 50.28; H, 4.26; N, 9.69.

According to the analysis of related databases, 6478-79-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mente?e, Emre; Emirik, Mustafa; Soekmen, Bahar Bilgin; Bioorganic Chemistry; vol. 86; (2019); p. 151 – 158;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-38-6, These common heterocyclic compound, 3034-38-6, name is 5-Nitro-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.

4-Nitroimidazole 6 (5.6 g, 50 mmol) was dissolved in a minimumamount of concentrated sulfuric acid and a mixture of fumingnitric acid (20 mL) and concentrated sulfuric acid (25 mL) wasadded to it. The resulting solution was refluxed for 5 h and aftercooling poured onto crushed ice and the mixture was adjusted topH 2 with sodium bicarbonate. The product was extracted byethyl acetate (3 50 mL). Concentration the extract yielded 7 asyellow crystals (3.5 g, 22 mmol); mp: 171-173 C (lit. mp166-169 cC) [41].

Statistics shows that 5-Nitro-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 3034-38-6.

Reference:
Article; Shirvani, Pouria; Fassihi, Afshin; Saghaie, Lotfollah; Van Belle, Siska; Debyser, Zeger; Christ, Frauke; Journal of Molecular Structure; vol. 1202; (2020);,
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. 615-15-6, name is 2-Methyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2

Method B. 2-Methylbenzimidazole (5 g) was added to a mixture of conc. sulfuric acid (70 mL) and water (55 mL) at 90 C. This was followed by the careful addition of powdered potassium dichromate (37 g). After 15-20 min. the mixture was quenched with ice-cold water and cooled to 0 C. Crystallization was induced by scratching the sides of the vessel. The precipitated acid was filtered, washed with water, alcohol, and finally with ether to give 19 g of the captioned product.

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 615-15-6.

Reference:
Patent; The Research Foundation of State University of New York; US5329012; (1994); A;,
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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5ClN2

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.

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

Reference of 144689-93-0,Some common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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 1; Ethyl 4-( 1 -hydroxy- 1 -methylethyl)-2-propyl- 1 – { 4- [2-(tetrazol-5-yi)phenyl]phenyl}methyl- imidazole-5-carboxylate (3); Acetone (200 ml) was added to the weighed ethyl ester of 4-(l -hydroxy- l-methylethyl)-2- propyl-lH-imidazole-5-carboxylic acid (1; 20 g), substance 2 (46.4 g), potash (40 g), and polyethylene glycol 400 (2 g). The resulting mixture was heated to the boil for H h. After filtering off the solids the filtrate was concentrated, ethanol (350 ml) was added to the concentrated filtrate, and the suspension was heated to the boil. After it was cooled to 15 C (20 minutes), the insoluble portion was sucked off and washed with ethanol (40 ml). After drying (50 0C, in vacuo), 50.7 g of the product (85 %) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, its application will become more common.

Reference:
Patent; ZENTIVA, A.S.; WO2007/48361; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16042-25-4,Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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.

The imidazole-2-carboxylic acid (10 g, 89.2 mmol) in suspension in thionyl chloride (160 mL) was heated to reflux, under agitation for 18 h. The reaction mixture was cooled, then filtered, washed with toluene, and dried under high vacuum to obtain a yellow solid (yield, 80-85%). M.p.: 164 C. 1H NMR (300 MHz, DMSO-d6) delta: 8.85 (s, 2H); 8.2 (s, 2H). 13C NMR (300 MHz, DMSO-d6) delta: 145.85, 144.95, 125.20, 120.15.

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

Reference:
Article; Moarbess, Georges; Guichou, Jean-Francois; Paniagua-Gayraud, Stephanie; Chouchou, Adrien; Marcadet, Olivier; Leroy, Fiona; Ruedas, Remi; Cuq, Pierre; Deleuze-Masquefa, Carine; Bonnet, Pierre-Antoine; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 268 – 274;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 14813-85-5, 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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Starting materials 16-18 (1 mmol) and K2CO3 (2 mmol) were suspended in DMF (1.8 mL) and stirred at 25 C for 30 min. 11 and 12, respectively (1.5 mmol) were added after 30 min and the solution was stirred at room temperature overnight. To the mixture was added ethyl acetate (5 mL) and water (5 mL).The aqueous layer was extracted several times with ethyl acetate (10 mL) and the combined organic layers were washed with brine, dried over MgSO4 and evaporated to dryness.

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-Phenyl-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Neudorfer, Catharina; Seddik, Amir; Shanab, Karem; Jurik, Andreas; Rami-Mark, Christina; Holzer, Wolfgang; Ecker, Gerhard; Mitterhauser, Markus; Wadsak, Wolfgang; Spreitzer, Helmut; Molecules; vol. 20; 1; (2015); p. 1712 – 1730;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 7098-07-9, name is 1-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

The reaction end point was monitored by adding 6.16 g (10 mmol) of M1 ‘, 0.96 g (10 mmol) of 1-ethyl tasteless, 50 mL of acetonitrile at room temperature for 48 h in a dry 100 mL three-necked flask. Washed with petroleum ether (100 mL x 3), the resulting viscous liquid was again Washed with ether (100 mL x 3) to give a yellow solid, Recrystallization from methylene chloride and drying in vacuo for 24 h afforded a pale yellow solid As the target compound (B2), 7.1 g, and the yield was 99percent.

The synthetic route of 7098-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central China Normal University; Zhang Aidong; Zhang Tiejiang; Duan Jiang; Tu Haiyang; (22 pag.)CN107188869; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem