Month: December 2020

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;,
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. 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);,
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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Methyl-1H-imidazole-4-sulfonyl chloride

The production of compound No. 26 proceeds according to the sequence of reaction steps shown in the following schemes: The first sub-step shown above was performed at 20 C. during 2 hours with a molar excess of CH2N2 (about 2 molar equivalents) in dry ether, then in a second sub-step (shown below) performed at 5 C. HCl gas was bubbled into the reaction mixture for 15 minutes, and the desired intermediate was obtained in 71% yield. For the conversion from 3 to 4, the first sub-step shown above was performed at 20 C. during 1 hour with a molar excess of thio-carbonyldiimidazole (about 2 molar equivalents) in THF, then in a second sub-step performed at 20 C. for 12 hours a 25% aqueous NH3 solution was added, and the desired intermediate was obtained in 72% yield. The conversion from 4 to 5 was performed during 6 hours with 1 molar equivalent NaHCO3 at reflux in methanol, and the desired intermediate was obtained in 92% yield. The conversion from 5 to 6 was performed during 3 hours at 20 C., and the desired intermediate was obtained in 90% yield. The conversion from 6 to the final compound was performed during 6 hours at 20 C. in 1,2-dichloroethane (DCE) in the presence of a molar excess of triethylamine (1.2 molar equivalents).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NV reMYND; US2010/197703; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 21252-69-7,Some common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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.

Silver(I)-N-octylimidazole complexes were alsosynthesized using a previously reported method with a minor modification. Typically, N-octylimidazole (2 mol equiv.) was added to a solution of AgNO3 (1 mol equiv.) in ethanol (15 mE) and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was filtered and evaporation of the solvent mixture gave a brown oil or cream solid. The brown oil was re-dissolved in dichloromethane and extracted three times with watet The organic phase was dried on anhydrous sodium sulfate and the solvent was removed under reduced pressure. Other silver(I)-N-alkylimidazole complexes were synthesized in the same manner. The solid complexes were further purified by recrystallization by dissolving in dichloromethane and precipitated with hexane.

The synthetic route of 21252-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kleyi, Phumelele; Maity, Arjun; Ray, Suprakas Sinha; (16 pag.)US2018/255777; (2018); A1;,
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. 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

PREPARATION 5 1-[2-Hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole (2.0 g) in thionyl chloride (10 ml) is warmed for one hour at 65. The excess thionyl chloride is removed in vacuo, the residue dissolved in dichloromethane (75 ml) and shaken with excess aqueous potassium carbonate. The organic layer is washed with water, dried over MgSO4, evaporated and the residue evacuated to remove all traces of dichloromethane, affording 1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole.

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; Syntex (U.S.A.) Inc.; US4272545; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 401567-00-8, 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. 401567-00-8 name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, 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.

4.1.27. 5-Aminomethyl-2-(4-isopropoxyphenoxy)-1-((2-(trime-thylsilyl)ethoxy)methyl)benzimidazole and 6-aminomethyl-2-(4-isopropoxyphenoxy)-1-((2-(trimethylsilyl)ethoxy)methyl)benzimidazole (24)To a solution of 18 (0.21 g, 0.50 mmol) in 25% aq NH3 (1.6 mL)and EtOH (16 mL) was added Raney Ni (1.6 mL, in water). The mix-ture was stirred for 4 h under a hydrogen atmosphere, then lteredthrough a Celite pad, and the ltrate was concentrated underreduced pressure. The residue was puried by silica gel columnchromatography (CHCl3/MeOH = 8:1) to afford the product 24(0.20 g, 97%, 1:1 regioisomeric mixture) as a yellow oil.1H NMR (500 MHz, CDCl3) d 7.51 (s, 1/2H), 7.48 (d, J = 8.6 Hz,1/2H), 7.43 (s, 1/2H), 7.31 (d, J = 8.0 Hz, 1/2H), 7.24-7.20 (m, 2H),7.19-7.14 (m, 1H), 6.95-6.90 (m, 2H), 5.50 (s, 1H), 5.46 (s, 1H),4.55-4.48 (m, 1H), 3.97 (s, 1H), 3.92 (s, 1H), 3.64 (t, J = 8.3 Hz,1H), 3.63 (t, J = 8.0 Hz, 1H), 1.34 (d, J = 6.0 Hz, 3H), 1.34 (d,J = 6.0 Hz, 3H), 0.93 (t, J = 8.0 Hz, 2H), 0.04 (s, 9/2H), 0.05 (s,9/2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Okazaki, Shogo; Noguchi-Yachide, Tomomi; Sakai, Taki; Ishikawa, Minoru; Makishima, Makoto; Hashimoto, Yuichi; Yamaguchi, Takao; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5258 – 5269;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2034-22-2,Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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 2,4, 5-tribromo- IH- imidazole (10.3 g, 32.8 mmol) in anhydrous N,N-dimethylformamide (100 ml) is slowly added NaH (1.4 g, 36.1 mmol, 60% in mineral oil) at room temperature. The suspension is stirred for 15 minutes and 2- (Trimethylsilyl)ethoxymethyl chloride (5.8 ml, 32.8 mmol) is added. The mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with water (250 ml) and extracted with ethyl acetate (3x 50 ml). The combined organic layer is washed with water (50 ml), brine, dried over MgSO4, filtered, and concentrated in vacuo to yield 2,4,5-tribromo-l-(2-trimethylsilanyl-ethoxymethyl)-lH-imidazole as a yellow waxy solid 13.8 g, 97 %.

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; FARMER, Bennett; FARROW, Neil Alexander; GAO, Donghong A.; HEIM-RIETHER, Alexander; KEENAN, Lana Louise Smith; MUGGE, Ingo Andreas; TAYLOR, Steven John; XIONG, Zhaoming; YU, Yang; ZHANG, Qiang; WO2010/45188; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1848-84-6, These common heterocyclic compound, 1848-84-6, name is 2-Ethyl-1H-benzo[d]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.

A mixture of 2- { 1 -[2-chloro-9-methyl-6-((5)-3-methylmorpholin-4-yl)-9H- purin-8-ylmethyl]piperidin-4-yl}propan-2-ol (200 mg, 0.47 mmol), 2-ethylbenzimidazole (73 mg, 0.50 mmol), tris(dibenzylideneacetone)dipalladium (12 mg, 2.5 molpercent), XPhos (20 mg, 10 molpercent) and Cs2CO3 (218 mg, 0.67 mmol) in DMF (6 mL) was purged with argon then heated at 150 0C for 1 h in a microwave reactor. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NEta3/MeOEta. The resulting residue was purified by column chromatography (Si-PCC, MeOH:DCM, 0-5percent) then (Si-PCC, MeOH:DCM, 0-3percent) affording 775 (95 mg, 38percent). LCMS (method I): Rx 2.65 min, [M+H]+ 533.3. 1H NMR (CDCl3, 400 MHz): delta 8.03-8.02 (1 H, m), 7.75-7.74 (1 H, m), 7.27-7.24 (2 H, m), 5.40 (2 H, brd s), 4.09-4.03 (1 H, m), 3.88 (3 H, s), 3.83 (2 H, s), 3.75-3.55 (4 H, m), 3.36 (2 H, q, J = 7.48 Hz), 2.98-2.95 (2 H, m), 2.11 (2 H, t, J = 10.92 Hz), 1.81-1.71 (2 H, m), 1.45-1.44 (6 H, m), 1.34-1.31 (4 H, m), 1.19 (6 H, s)

Statistics shows that 2-Ethyl-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 1848-84-6.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem