Month: August 2021

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 60-56-0 as follows. name: 1-Methyl-1H-imidazole-2(3H)-thione

Add 1-methylimidazole-2-thiol (0.25 g, 2.16 mmol) to a 50 mL round bottom flaskAnd potassium carbonate (0.89g, 6.48mmol) (20mL) in acetonitrile was stirred at room temperature for 1 hour and nitrogen.Intermediate IX (0.70 g, 2.16 mmol) was then added to the reaction mixture.Stirring was carried out at 80 C for 12 hours under reflux. Thin layer chromatography was followed until the end of the reaction.The solvent is distilled off under reduced pressure, and then concentrated, extracted, and separated by column chromatography.After drying and the like, the compound IV (400 mg) was obtained in a yield of 51.7%.White solid, melting point > 250 C.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Southwest University; Zhou Chenghe; Ba Tini·nasaiya; Li Zhenzhen; (17 pag.)CN109535176; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

Example 1; Inventive; A flask is charged with 531.5 g of dry dichloromethane and 93.8 g (1.37 mol) of imidazole and this initial charge is heated to 35 C. At this temperature over the course of 1.75 hours 36.04 g (0.36 mol) of phosgene are added with an introduction rate of 20.6 g/h. The mixture thus obtained is subsequently stirred at the same temperature for 1.5 h. In order to ensure a phosgene-free reaction mixture, 13.2 g of distillate are taken off under a pressure of 790 to 500 mbar and at 35-25 C., an ammonia/water/isopropanol mixture is added to the distillate, and this mixture is discarded. The imidazole hydrochloride by-product (isolated dry weight: 72.1 g) is removed by filtration at 35 C., the filter cake being washed with twice 100 ml of warm dichloromethane at 33 C. 250.1 g of water-clear solution are distilled off from the combined organic phases at 790 to 500 mbar and 35-25 C. The remaining solution is cooled to 0 C., and a suspension forms. The precipitated carbonyl bisimidazole is separated off by filtration and additionally washed with 50 ml of dichloromethane conditioned to a temperature of 0 C. Drying of the crystals at 4 mbar and 30 C. gives 40.0 g of product in the form of white crystals, Hazen colour number: 69.7. The purity of the product is 99.3%, corresponding to a yield of 71.2% of theory.; Example 5 Inventive with Recycling of the Mother Liquor 1st Phosgenation A flask is charged with 531.5 g of dry dichloromethane and 93.8 g (1.37 mol) of imidazole and this initial charge is heated to 35 C. At this temperature over the course of 1.75 hours 35.02 g (0.35 mol) of phosgene are added with an introduction rate of 20.0 g/h. The mixture thus obtained is subsequently stirred at the same temperature for 1.5 h. In order to ensure a phosgene-free reaction mixture, 8.4 g of distillate are taken off under a pressure of 750 to 500 mbar and at 35-20 C., an ammonia/water/isopropanol mixture is added to the distillate, and this mixture is discarded. The imidazole hydrochloride by-product (isolated dry weight: 80.3 g) is removed by filtration at 35 C., the filter cake being washed with twice 100 ml of warm dichloromethane at 33 C. The remaining solution is cooled to 0 C., and a suspension forms. The precipitated carbonyl bisimidazole is separated off by filtration and additionally washed with 50 ml of dichloromethane conditioned to a temperature of 0 C. After the solid carbonylbisimidazole has been filtered off, 553.0 g of mother liquor M1 are obtained. Drying of the crystals at 5 mbar and 20 C. gives 33.54 g of product in the form of white crystals with a Hazen colour number of 45.1. The purity of the product is 99.6%. The yield therefore corresponds to 59.9% of theory. 2nd Phosgenation A flask is charged with 531.5 g of dichloromethane-containing mother liquor M1 from the 1st phosgenation step and 93.8 g (1.37 mol) of imidazole and this initial charge is heated to 35 C. At this temperature over the course of 1.75 hours 35.02 g (0.35 mol) of phosgene are added with an introduction rate of 20.0 g/h. The mixture thus obtained is subsequently stirred at the same temperature for 1.5 h. In order to ensure a phosgene-free reaction mixture, 21.6 g of distillate are taken off under a pressure of 750 to 450 mbar and at 35-20 C., an ammonia/water/isopropanol mixture is added to the distillate, and this mixture is discarded. The imidazole hydrochloride by-product (isolated dry weight: 86.6 g) is removed by filtration at 35 C., the filter cake being washed with twice 100 ml of warm dichloromethane at 33 C. The remaining solution is cooled to 0 C., and a suspension forms. The precipitated carbonyl bisimidazole is separated off by filtration and additionally washed with 100 ml of dichloromethane conditioned to a temperature of 0 C. After the solid carbonylbisimidazole has been filtered off, 553.0 g of mother liquor M2 are obtained. Drying of the crystals at 6 mbar and 30 C. gives 39.4 g of product in the form of white crystals with a Hazen colour number of 33.2. The purity of the product is 98.7%. The yield therefore corresponds to 70% of theory. 3rd Phosgenation A flask is charged with 531.5 g of dichloromethane-containing mother liquor M2 from the 2nd phosgenation step and 93.8 g (1.37 mol) of imidazole and this initial charge is heated to 35 C. At this temperature over the course of 1.75 hours 35.02 g (0.35 mol) of phosgene are added with an introduction rate of 20.0 g/h. The mixture thus obtained is subsequently stirred at the same temperature for 1.5 h. In order to ensure a phosgene-free reaction mixture, 9.2 g of distillate are taken off under a pressure of 750 to 500 mbar and at 35-20 C., an ammonia/water/isopropanol mixture is added to the distillate, and this mixture is discarded. The imidazole hydrochloride by-product (isolated dry weight: 88.1 g) is removed by filtration at 35 C., the filter cake being washed with twice 100 ml of warm dichloromethane at 33 C. The remaining solution is cooled to 0 …

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Job, Andreas; Griehsel, Bernd; US2005/272937; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Compound A1 (16.1 g, 100 mmol) was sequentially added to the flask under argon gas protection.Compound B1 (12.3 g, 105 mmol), Pd(PPh3) 4 (2.31 g, 2 mmol),Toluene (300 ml), aqueous sodium carbonate (2M, 150 ml),Stir under reflux for 8 hours. After cooling the above reaction solution to room temperature,Extract with toluene and combine the organic phases.The organic phase is washed with saturated brine, and the organic phase is dried and concentrated.Column chromatography was carried out using silica gel as a stationary phase to give Compound D1.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Han Chunxue; Sun Jing; (31 pag.)CN108892690; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15469-97-3, 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. 15469-97-3 name is 1-Trityl-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.

EXAMPLE 55 STR85 Preparation of (+-)trans-4-(2-(4-cyclohexylbut-1-ynyl)cyclopropyl)imidazole (55). (+-)trans-4-(2-(4-Cyclohexylbut-1-ynyl)cyclopropyl)imidazole was prepared as described for the Example 38 except recemic mixture of 4-(2-ethylnylcyclopropyl)-1-(triphenylmethyl)imidazole and 2-cyclopentyl iodoethane were used. (+-)trans-4-(2-(4-cyclohexylbut-1-ynyl)cyclopropyl)imidazole (55). 1 H-NMR (300 MHz, CD3 OD): delta 7.51 (s, 1H), 6.81 (s, 1H), 2.14 (m, 2H), 2.04 (m, 1H), 1.72 (m, 5H), 1.42 (m, 1H), 1.35 (m, 3H), 1.29-1.02 (m, 5H), 0.9 (m, 2H); MS (Cl) m/e 243(M+1).

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

Reference:
Patent; Gliatech, Inc.; US6008240; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 7152-24-1, 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. 7152-24-1, name is 2-(Methylthio)benzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 2.01 g (0.01 mol) of 4-methoxy-3-nitrobenzyl chloride (1), 0.01 mol of heterocycle 3-6, and 1.38 g (0.01 mol) of potassium carbonate in 20 mL of DMF was stirred for 5 h at 80-90 C. The mixture was cooled to room temperature, poured into 70 mL of water, and left overnight in the cold, and the precipitate was filtered off, dried, and recrystallized.

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, 2-(Methylthio)benzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Harutyunyan; Russian Journal of Organic Chemistry; vol. 52; 1; (2016); p. 76 – 79; Zh. Org. Khim.; vol. 52; 1; (2016); p. 83 – 86,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4856-97-7, 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1H-benzimidazolyl methanol (2 g, 13.5 mmol) and sodium hydroxide (0.8 g, 20.3 mmol) were dissolved in 20 ml of water.Potassium permanganate (63.9 g, 41 mmol) was added under cooling and stirred at 80 C overnight.After the reaction is completed, the mixture is filtered, and the pH of the filtrate is adjusted to about 3 to precipitate a brown solid.The product was dried to about 1.76. Yield: 78%.

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, (1H-Benzoimidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Song Meng; (13 pag.)CN110156708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 45676-04-8, 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 45676-04-8 as follows.

To a 250 mL three-necked flask, 6.8 g of N-tert-butylimidazole and 9.3 g (molar ratio 1: 1) of chloroform were added to a reactor equipped with a magnetic stirrer, a heating apparatus and a condensing apparatus, and toluene was added as a solvent , 2.5 g of sodium hydride as the catalyst, at 90 C, stirring reaction 12h, separation and purification of N-tert-butyl imidazole. 6.2 g of the above product and 6.2 g (molar ratio 1: 1) of chloromethyltrimethylsilane were added to a reaction vessel equipped with a magnetic stirrer, a heating apparatus and a condensing apparatus, 100 mL of toluene as a solvent, argon gas, 120 C for 24 h, and purified to obtain N-methylsilyl (trimethyl) imidazole type ionic liquid.

According to the analysis of related databases, 45676-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Normal University; Bai, Ying; Peng, Jiajian; Yang, Xioaling; Zhang, Fengxiang; Li, Jiayun; Xiao, Wenjun; (8 pag.)CN106380487; (2017); A;,
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. 2302-25-2, name is 4-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-1H-imidazole

(Example 177) 2-(4-{2-Fluoro-5-[3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl]phenyl}-1H-imidazo1-1-yl)ethanol (Compound No. 2-700) (177a) 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole 2-Bromoethanol (1.4 mL, 20 mmol) was dissolved in methylene chloride (50 mL), and triethylamine (3.5 mL, 25 mmol) and trityl chloride (7.0 g, 25 mmol) were added thereto. The resulting mixture was stirred at room temperature for 6 hr. To this reaction solution, water was added. After extraction with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluding solvent: hexane/ethyl acetate) to obtain 4.4 g (yield: 60%) of 2-bromoethyl trityl ether as a white solid. N,N-Dimethylformamide (10 mL) was added to a mixture of the resulting 2-bromoethyl trityl ether (1.9 g, 5.1 mmol) and 4-bromoimidazole (0.68 g, 4.6 mmol). The resulting mixture was cooled to 0C, and sodium hydride (60%, oil, 0.22g, 5.5 mmol) was added thereto. The mixture was warmed to room temperature and then stirred for 6 hr. To this reaction solution, water was added. After extraction with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluting solvent: hexane/ethyl acetate) to obtain 1.4 g (yield: 69%) of the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) delta ppm: 7.45 (1H, s), 7.29-7.22 (15H, m), 6.89 (1H, s), 4.00 (2H, t, J = 4.9 Hz), 3.36 (2H, t, J = 4.9 Hz).

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 2302-25-2.

Reference:
Patent; Sankyo Company, Limited; EP1798229; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone, 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. Recommanded Product: 1-(1-Methyl-1H-imidazol-2-yl)ethanone

A mixture of N-(4-ethynylphenyl)-2-(4-formylphenyl)acetamide (184 mg, 0.7 mmol), N-methyl imidazole ketone 2b (99 mg, 0.8 mmol, 1.2 equivalents), piperidine (0.2 ml, 2.1 mmol, 3 equivalents) and anhydrous methanol (5 ml) placed in a 10 mL microwave vial was heated in a microwave synthesizer at 85 C for 6 hours. The crude reaction mixture was concentrated and purified by flash chromatography on silica gel in ethyl acetate/ hexanes (20 %-> 70% ethyl acetate) to obtain 41 (59 mg, 23%). NMR (600 MHz, CDC13) delta 8.09 (d, J = 15.9 Hz, 1H), 7.80 (d, J = 16.0 Hz, 1H), 7.70 (t, J = 6.9 Hz, 2H), 7.39 (s, 4H), 7.35 (d, J = 8.0 Hz, 2H), 7.22 (s, 1H), 7.11 (s, 1H), 7.08 (s, 1H), 4.09 (s, 3H), 3.74 (s, 2H), 3.01 (s, 1H).HRMS calculated 370.1556 found 370.1563 [M+H]+ ion.

The synthetic route of 85692-37-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF TOLEDO; TILLEKERATNE, Viranga; AL-HAMASHI, Ayad; DLAMINI, Samkeliso; ALQAHTANI, Abdulateef, Saeed; KARAJ, Endri; (69 pag.)WO2019/36607; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26663-77-4, name is Methyl benzimidazole-5-carboxylate, 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 26663-77-4, category: imidazoles-derivatives

8.2. PREPARATION OF 3,4-DIISOTHIOCYANATOBENZOIC ACID, METHYL ESTER, 11 A 250 ml round bottom flask was charged with 4.98 g (50 mmol) of calcium carbonate, 10 ml of methylene chloride, and 3 ml of water. The resultant slurry was cooled to 10 C. and then 2.27 ml (3.43 g, 30 mmol) of thiophosgene (Aldrich) followed by 2.50 g (14.2 mmol) of 5-benzimidazolecarboxylic acid, methyl ester, 10, dissolved in 50 ml of a 1:1 mixture of acetonitrile in water were slowly added. The reaction mixture was stirred for 4 h and the temperature was allowed to rise to 15-20 C. The orange-white reaction slurry was then filtered and the filtrate was washed with three 50 ml portions of methylene chloride. The organic layers were combined, dried over MgSO4, filtered, and the solvents were removed under vacuum to leave a beige residue. This residue was triturated four times with petroleum ether to leave, after drying for 16 h at 25 C. at 30 mm pressure, 2.14 g (8.56 mmol, 60% yield) of 3,4-diisothiocyanatobenzoic acid, methyl ester, 11, as an off-white powder. 1 H NMR (CDCl3, TMS): delta7.85-7.95 (m, 2H), 7.30 (d, 1H), 3.92 (s, 3H). IR showed a doublet (NCS) at 2140 cm-1.

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, Methyl benzimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytogen Corporation; US5585468; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem