Tag: M.W=100-200

Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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. Safety of 1-Methyl-1H-imidazole-4-carboxylic acid

Production Example 6N-(3-Bromo-4-fluorobenzyl)-1-methyl-N-(tetrahydro-2H-thiopyran-4-yl)-1H-imidazole-4-carboxamideA mixture of N-(3-bromo-4-fluorobenzyl)tetrahydro-2H-thiopyran-4-amine (1.72 g), 1-methyl-1H-imidazole-4-carboxylic acid (0.71 g), EDC.HCl (1.63 g), HOBt (0.87 g), dimethylformamide (30 mL) and triethylamine (1.8 mL) was stirred overnight at room temperature.The solvent was distilled off under reduced pressure and after extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate.After filtering off the desiccant, the solvent was concentrated.The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (1.55 g).1H NMR (200 MHz, CHLOROFORM-d) d ppm 1.65-2.27 (m, 4H) 2.51-2.93 (m, 4H) 3.64-3.81 (m, 3H) 4.41-5.55 (m, 3H) 6.93-7.62 (m, 5H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41716-18-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2012/10414; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, molecular formula is C6H6N4, 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. Computed Properties of C6H6N4

2,2′-Biimidazole (0.33 g, 2.48 mmol) and NaOH (0.39 g, 9.92 mmol) were placed in a 100 mL round bottomed flask with 20 mL of acetonitrile. The mixture was stirred at room temperature for two hours. Benzyl bromide (0.63 g, 5 mmol) in acetonitrile (20 mL) was added to the mixture and refluxed for 24 h at 50-60 C. The reaction was monitored with TLC and after completion the solvent was removed by rotary evaporation. The residue was dissolved in water (50 mL) and extracted with methylene chloride (30 mL * 3). Organic layers were combined, dried over anhydrous MgSO4 and rotary evaporated to obtain the yellow color powder as the product. Yield: 0.69 g (89%); mp 144-146 C; 1H NMR (deltaH; CDCl3, 400 MHz):5.70 (s, 4H), 6.93 (d, 2H), 7.03 (m, 4H), 7.12 (d, 2H), 7.24 (m, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 492-98-8, its application will become more common.

Reference:
Article; Aakeroey, Christer B.; Wijethunga, Tharanga K.; Desper, John; Journal of Molecular Structure; vol. 1072; 1; (2014); p. 20 – 27;,
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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. 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 872-82-2

General procedure: 0.291 g (1 mmol) of cobalt(II) nitrate hexahydrate was dissolvedin 5 mL of methanol. In a separate flask 0.224 g (2 mmol) 4(5)-(bhydroxyethyl)imidazole was dissolved in 5 mL of methanol. Bothsolutions were mixed and refluxed for 60 min. The resulting solutionwas left to evaporate in room temperature. After severalmonths reddish crystals of 1 were formed in the initially obtainedpink oil.

According to the analysis of related databases, 872-82-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ciborska, Anna; Do??ga, Anna; Kentner, Weronika; Ma?lewski, Piotr; Wyrzykowski, Dariusz; Polyhedron; vol. 178; (2020);,
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Imidazole | C3H4N2 – PubChem

Reference of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of n-BuLi (2.5 M in hexanes, 1.2 mL, 3.0 mmol) was added dropwise by syringe to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (570.8 mg, 3.261 mmol) in dry THF (6 mL) in a dry ice-acetone bath. After 1-2 minutes, a solution of (4-chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (0.790 g, 1.626 mmol, Intermediate 47: step b) in dry THF (2 mL) was added dropwise. The reaction was stirred for 5 minutes, then was moved into an ice bath and allowed to warm to ambient temperature. The reaction was quenched with saturated aqueous ammonium chloride. The mixture was partitioned between water and dichloromethane. The separated aqueous phase was further extracted with dichloromethane. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) followed by reverse-phase HPLC (acetonitrile/H2O+0.05% TFA). The product fractions were basified with saturated aqueous sodium bicarbonate and extracted with DCM, before being dried (Na2SO4), filtered, and concentrated to dryness to provide the title compound. 1H NMR (400 MHz, CDCl3) delta 8.76 (d, J=2.0 Hz, 1H), 8.13 (d, J=2.2 Hz, 1H), 7.79-7.73 (m, 2H), 7.57 (dd, J=8.1, 0.9 Hz, 1H), 7.41 (dd, J=8.7, 2.2 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.94 (d, J=8.0 Hz, 1H), 6.04 (s, 1H), 4.35 (s, 2H), 4.08 (s, 3H), 3.39 (s, 3H), 2.53 (s, 3H), 2.41 (s, 3H), 2.37 (s, 3H); MS m/e 582.2 [M+H]+.

The synthetic route of 5-Bromo-1,2-dimethyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
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Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, 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. category: imidazoles-derivatives

Step 4) Methyl 2-[4-[(2-Propyl-1H-benzimidazol-1-yl)methyl]phenyl]-1-cyclopentene-1-carboxylate To a cooled (0 C.), stirred partial solution of 2-propyl-1H-benzimidazole (0.79 g, 4.96 mmol) in DMF (4 mL) was added NaH (60% dispersion in mineral oil; 0.20 g, 4.96 mmol). After 1.5 h, a solution of methyl [2-[(4-chloromethyl)phenyl]-1-cyclopentene]-1-carboxylate (1.13 g, 4.51 mmol) in DMF (1.5 mL) was added and the resultant mixture was stirred at room temperature for 18 h. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried, and concentrated. Purification by flash chromatography (30% EtOAc/hexane) gave 1.63 g (96%) of product as a yellow oil. 1 H NMR (CDCl3) delta 1.00 (t, J=7.5 Hz, 3H), 1.86 (m, 2H), 1.95 (m, 2H), 2.79 (m, 6H), 3.59 (s, 3H), 5.33 (s, 2H), 6.99 (d, J=8.2 Hz, 2H), 7.28 (m, 5H), 7.77 (d, J=7.5 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5465-29-2, its application will become more common.

Reference:
Patent; American Home Products Corporation; US5283242; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1849-01-0, These common heterocyclic compound, 1849-01-0, name is 1-Methyl-1H-benzo[d]imidazol-2(3H)-one, 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 69 1,3-Dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazol-2-one potassium tert.-butoxide, 2.1 g (18.5 mmol). was added to a solution of 2.5 g (16.9 mmol) of 1,3-dihydro-1-methyl-2H-benzimidazol-2-one in 25 ml of dimethylformamide. After stirring under nitrogen for 15 minutes, 2.21 g (18.5 mmol) of propargyl bromide was added and the mixture was stirred at room temperature for 30 minutes. It was diluted with ice-water and the precipitate was filtered off washed with water and sucked dry. The crude product was passed over silica gel using 10% (v/v) of ethyl/acetate in methylene chloride for elution. Crystallization from ethyl acetate/hexane gave colorless crystals of 1,3-dihydro-1-methyl-3-(2-propynyl)-2H-benzimidazole-2-one with m.p. 110-112.

The synthetic route of 1849-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4959361; (1990); 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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

According to the analysis of related databases, 7189-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, 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 939-70-8 as follows.

General procedure: A solution of 2-acetyl-benzimidazole 4(3.2 g, 20 mmol) and the diversely substituted aromatic aldehydes5a-h (24 mmol) in 40 ml of absolute methanol were taken in a flask.Potassium hydroxide (8.0 g, 142.6 mmol) was added and the reactionmixture was stirred for 24 h at room temperature under TLCmonitoring. The mixture was then poured into crushed ice water.The product obtained is filtered and washed with distilled waterand finally recrystallized from methanol.

According to the analysis of related databases, 939-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Djemoui, Amar; Naouri, Abdelkader; Ouahrani, Mohammed Ridha; Djemoui, Djamila; Lahcene, Souli; Lahrech, Mokhtar Boualem; Boukenna, Leila; Albuquerque, Helio M.T.; Saher, Liza; Rocha, Djenisa H.A.; Monteiro, Fatima Liliana; Helguero, Luisa A.; Bachari, Khaldoun; Talhi, Oualid; Silva, Artur M.S.; Journal of Molecular Structure; vol. 1204; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 583-42-6, name is 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione, 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. Computed Properties of C7H5FN2S

Step 2) Synthesis of 2-chloro-5-fluoro-1H-benzo [d] imidazole To a 50 mL of reaction flask were added 5-fluoro-1H-benzo [d] imidazole-2-thiol (1.00 g, 6.57 mmol) and phosphorus oxychloride (25 mL) . The mixture was refluxed for 13 h. After the reaction is complete, the mixture was concentrated to remove excess phosphorus oxychloride. The resulting mixture was quenched with saturated sodium bicarbonate solution (15 mL) , and extracted with ethyl acetate (10 mL ? 3) . The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a pale yellow solid (1.03 g, 92.0%) .MS (ESI, pos. ion) m/z: 171.05 [M+H] +.

The synthetic route of 5-Fluoro-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 54624-57-6, name is 2-Bromobenzimidazole, 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 54624-57-6, COA of Formula: C7H5BrN2

Sodium hydride (60% dispersion in mineral oil, 0.665 g, 16.63 mmol) was added to a solution of 2-bromo-1H-benzo[d]imidazole (2.73 g, 13.86 mmol) in DMF (30 mL), and the reaction stirred for 10 minutes at ambient temperature. 1-Bromo-2-methoxyethane (1.541 ml, 16.63 mmol) was added, and reaction stirred overnight at ambient temperature. The reaction was diluted with ethyl acetate and washed several times with brine. The organic layer was separated and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified via column chromatography on a 100 gram silica gel column eluting with 20-40% ethyl acetate-hexane. The desired fractions were combined and concentrated to afford 2-bromo-1-(2-methoxyethyl)-1H-benzo[d]imidazole (2.9 g, 82%) as an orange oil. 1H NMR (300 MHz, DMSO-d6) delta ppm 7.54-7.67 (m, 2H) 7.14-7.34 (m, 2H) 4.42 (t, J=5.28 Hz, 2H) 3.67 (t, J=5.28 Hz, 2H) 3.20 (s, 3H).

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-Bromobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Forma Therapeutics, Inc.; Bair, Kenneth W; Barczak, Nicholas; Han, Bingsong; Lancia, JR., David R.; Liu, Cuixian; Martin, Matthew W; Ng, Pui Yee; Rudnitskaya, Aleksandra; Thomason, Jennifer R; Zablocki, Mary Margaret; Zheng, Xiaozhang; (195 pag.)US2016/264518; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem