Category: imidazoles-derivatives

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

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

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

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

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

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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 1-Trityl-1H-imidazole-4-carbaldehyde

Step 8.c. 7-((1-Triphenylmethyl-imidazol-4-yl)methyl)-2-(2-methoxyphenyl)-8-(1-methylpropyl)- 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine 8-(1-Methylpropyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyrazine dihydrochloride (compound vii where R3 is 1-methylpropyl, R4 is 2-methoxyphenyl, and R5-R7 are H) (from Step 4.g.)(179 mg, 0.50 mmol) and the product from Step 8.b. (compound xiv where R2 is H) (338 mg, 1.00 mmol) were combined in 1,2-dichloroethane (2.0 ml). NaBH(OAc)3 (212 mg, 1.00 mmol) was added and the reaction was allowed to stir at room temperature for about 1 hour.. The reaction mixture was poured onto a silica gel column and the product was eluted using EtOAc as eluant.. Product fractions were combined and concentrated to yield pure product as white foam (150 mg, 49%).. Mass spec. 608.2, MH+.

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 23814-14-4, 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. 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 9; 2-Oxo-N-(2-oxo-2,3-dihydro-1 H-benzo [d] imidazol-5-yl)-2,3-dihydro-1 H- benzo[d]imidazole-5-carboxide (referred to as DC-0051-Bl); The amide was synthesized by reacting 2-oxo-2, 3-dihydro-lH- benzoimidazolyl-5-carboxylic acid with 5-amino-2, 3-dihydro-lH-benzoimidazol-5- one in the presence of 1,3- N, N-diisopropylcarbodiimide and 1- hydroxybenzotriazole. 1,3- N, N-Diisopropylcarbodiimde (0.504 g; 4 mmol) was added to a solution of 2-oxo-2,3-dihydro-lH-benzoimidazole-5-carboxylic acid (0.448 g; 2.5 mmol), 5- amino-2-oxo-2,3-dihydro-lH-benzoimidazole and 1-hydroxybenzotriazole (0.34 g; 2.5 mmol) in anhydrous N, N-dimethylformamide (10 ml). The reaction mixture was stirred at 40 C for 12 hours. The precipitated product was isolated by filtration of the reaction mixture followed by washing three more times with N, N-dimethylformamide (3 ml). The product was dissolved in dimethylsulfoxide (5ml) and precipitated by diluting the solution with acetonitrile (60 ml). Filtration and drying under vacuum gave 2-Oxo-N-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2,3-dihydro-1H- benzo [d]imidazole-5-carboxide (also referred to as DC-0051-B1) (0.22 g; 28%). ¹H NMR ((CD3)2SO 10.62 (1H, s, NH), 10.53 (1H, s, NH), 9.98 (lH, s, NH) 7.65 (1H, d, J 8Hz) 7.55 (2H, bs) 7.23 (1H, d, J 8Hz) 7.05 (1H, d, J 8Hz) 7.85 (1H, d, J 8Hz).

The synthetic route of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
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. 16681-56-4, name is 2-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 16681-56-4

To 2-bromo-lH-imidazole (0.073 g, 0.5 mmol), 3-(bromomethyl)pyridine hydrobromide (0.139 g, 0.550 mmol) and potassium carbonate (0.223 g, 1.614 mmol) was added acetone (15 mL). This mixture was stirred for 18 h at RT. The solvent was then removed in vacuo yielding a brown residue. This residue was then partitioned between ethyl acetate (35 mL) and water (35 mL) and the phases separated. The aqueous phase was then extracted twice with ethyl acetate (2×35 mL), the organics combined and then dried using a hydrophobic frit. The solvent was then removed in vacuo yielding a yellow oil as the title compound (107 mg, 0.449 mmol, 90%). LCMS (System B): tRET = 0.56 min; MH+ 238, 240.

The synthetic route of 16681-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen system imidazole was dissolved in anhydrous THF and added dropwise slowly an appropriate amount of acetic anhydride (acetic anhydride), then the reaction exotherm, i.e. about half an hour to complete the reaction; After completion of the reaction, concentration under reduced pressure, and evacuated the solvent was removed to give a solid product, and solid was rinsed with n – hexane and filtered to give a white solid of compound 11, yield about 98percent.The system under nitrogen compound 11 was dissolved in dichloromethane and at 0 Compound 3 was gradually added dropwise to the solution, followed by return to room temperature for about two hours, the solution was added diethyl ether to form a solid precipitate, The solid was filtered, then the solid was rinsed with diethyl ether, to give the compound 10 as a white solid, a yield of about 81percent.

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

Reference:
Patent; ETERNAL MATERIALS CO., LTD.; CHENG, PI JEN; CHOU, MENG YEN; LEE, CHUAN ZONG; WU, CHUNG JEN; (47 pag.)TWI516478; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4856-97-7, 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 4856-97-7 as follows.

To 1.2 eq. (2.3 g, 0.041 mol) of KOH dissolved in a 50percent (v/v) water?ethanol mixture (14 mL), 5.1 g (0.034 mol) of 1-(1H-benzimidazol-2-yl) methanol was added. The solution was cooled to 0 °C, and 5 mL of dimethyl sulfate was added dropwise over 30 min (the temperature of the mixture did not exceed 5 °C). The mixture was kept under stirring at 0 °C for 30 min and at room temperature for additional 15 min. The solid obtained was recovered by filtration and washed with water, giving the title compound as a white solid. It was purified by recrystallization from a mixture of CH3CN/EtOH. White solid; Yield: 4 g (72percent); M.p. 122?124 °C; 1H NMR (250 MHz, CDCl3): delta 7.76?7.64 (m, 1H), 7.29?7.19 (m, 3H), 5.13 (OH, br s, 1H), 4.88 (CH2, s, 2H), 3.81 (N-CH3, s, 3H); FT-IR (4000?600 cm?1): 3450?2800, 1639, 1454, 1312, 1007, 860, 744, 567; UV?vis (MeOH) (lambdamax, nm (logepsilon, M?1 cm?1): 280(5.35), 268(5.18), 244(5.14), 219(5.06).

According to the analysis of related databases, 4856-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Benhassine, Anfel; Boulebd, Houssem; Anak, Barkahem; Bouraiou, Abdelmalek; Bouacida, Sofiane; Bencharif, Mustapha; Belfaitah, Ali; Journal of Coordination Chemistry; vol. 71; 2; (2018); p. 311 – 328;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem