Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-1H-imidazole, 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 2302-25-2, SDS of cas: 2302-25-2

Step A. (Z -4-(3-(4-(4-Bromo- lH-imidazol- 1 -yl but-2-en- 1 -yr)-4,4-dimethyl-2,5- dioxoimidazolidin- 1 -yl)-2-(trifluoromethyl)benzonitrile. A mixture of (Z)-4-(3-(4-chlorobut-2-en-l-yl)-4,4-dimethyl-2,5-dioxoimidazolidin-l-yl)-2- (trifluoromethyl)benzonitrile (500 mg, 1.3 mmol), 4-bromo-lH-imidazole (191 mg, 1.3 mmol), and K2C03 (359 mg, 2.6 mmol) in DMF (5 mL) was stirred at room temperature for 5 hours. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL x 3). The extracts were combined, washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford (Z)-4-(3-(4-(4- bromo- 1 H-imidazol- 1 -yl)but-2-en- 1 -yl)-4,4-dimethyl-2,5-dioxoimidazolidin- 1 -yl)-2- (trifiuoromethyl)benzonitrile as a white solid (600 mg, 93%). LCMS (ESI) m/z: 496.1 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BEAUFOUR-IPSEN (TIANJIN) PHARMACEUTICAL CO., LTD.; AUVIN, Serge; LANCO, Christophe; DUTRUEL, Oliver; CHAO, Qi; GU, Kaichun; WO2015/100617; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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 7; 2-Chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole; To a suspension of sodium hydride (6.2 g, 245 MMOL) in DMF (275 mL) at 5 C was added 2-chlorobenzimidazole (37 G, 243 MMOL) via a solid-addition funnel over 30 min while maintaining the internal temperature of the mixture below 10 C. An additional 25 mL of DMF was added, and the ice bath was removed. After 2 h, 2-(TRIMETHYLSILYL) ETHOXYMETHYL CHLORIDE (SEM-CI) was added dropwise over 5 min. A white precipitate formed. The reaction mixture was stirred at room temperature for 18 h. To the mixture was added H20 (500 mL) and ethyl acetate (750 mL). The organic layer was washed with additional H20 (500 mL), dried (MGS04), and concentrated under reduced pressure, giving 65.8 g (96% yield) of the desired product as a clear golden oil, which solidified upon standing to give a beige solid. TLC (SI02, 5% ACETONE/CH2CI2) : Rf = 0.64. MS (ESI) : mass calculated for C13H19CIN2OSI, 282.10 ; m/z found, 283. 1. H NMR (400 MHz, CDC13) : 7.70 (d, J = 7.3, 1 H), 7.46 (d, J = 7.6, 1 H), 7.40-7. 25 (m, 2H), 3.58 (t, J = 7.9, 2H), 0.92 (t, J = 8.3, 2H), 0.04 (s, 9H)

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/12296; (2005); 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 152628-03-0

Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid 50.0g (229mmol) and polyphosphoric acid added and stirred and 300 g, heated to around 70 C., the reaction solution obtained was stirred for 30 minutes, added in portions over a period N- methyl -O- phenylenediamine 45.0g of (368mmol) 2 hours It was.After adding the entire amount, stirring for 1 hour at around 70 C., and stirred for 5 h warmed to near yet 130. C..After confirming the disappearance of 4-methyl–2-n-propyl -1H- benzimidazole-6-carboxylic acid by HPLC, was cooled to about 70 C., while maintaining the water 600g The temperature of the reaction solution at 70 to 85 C. It was dropped little by little.After the total amount dropwise, 30 C. and cooled to near, pH of the reaction solution with aqueous ammonia was adjusted to be pH 8.3, after stirring for 1 hour warmed to around 50 C., the solid by vacuum filtration It is filtered off and washed the solid was filtered off with water 200g in the vicinity of 50 , to obtain a wet product of light brown crystals.Stirring blade, a thermometer, three-neck flask 1L fitted with condenser, was added and stirred the wet product of the resulting pale brown crystals and water 900 g, after stirring for 1 hour warmed to around 50 C. , vacuum filtered off the solids by filtration, wash the solid was filtered off with 100g of water around 50 C., the resulting wet product was dried for 15 hours under reduced pressure, a pale crude benzimidazole body as brown crystals to obtain a body 60.3g.The crude product of the benzimidazole body was analyzed by HPLC, the purity was 98.20%, the content of methyl benzimidazole body 0.14%, the content of ethyl benzimidazole body with 0.07% there were. stirring blade, a thermometer, three-necked flask 100mL fitted with a condenser, a mixture of a crude product 5.0g of methanol 12g and water 50g benzimidazole body obtained in Production Example 1 was added after stirring on, the addition of hydrochloric acid 2.1g containing hydrogen chloride 0.78 g (21.4 mmol), stirred for 10 minutes at about 25 C., the solid in the reaction solution was confirmed to be dissolved.Then, was added aqueous ammonia 1.1g containing ammonia 0.28 g (16.5 mmol), precipitation of white crystals was confirmed.After stirring for 1 hour at about 25 C., vacuum filtered through the solid was filtered off, the solid was filtered off with water 5g were washed twice and dried for 12 hours at 60 C. under reduced pressure and the resulting wet biomass, to obtain a benzimidazole body 4.2g (13.9mmol) as white crystals.Recovery rate, which is calculated based on the mass of the crude product of the benzimidazole body was 84.4%.As a result of the benzimidazole body obtained was analyzed by HPLC, the purity was 99.56%, the content of methyl benzimidazole body 0.06%, the content of ethyl benzimidazole body 0.02% met.

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 152628-03-0.

Reference:
Patent; TOKUYAMA CORPORATION; MIYAOKU, TAKAYUKI; (16 pag.)JP2015/160810; (2015); 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., Product Details of 7189-69-7

A solution of n-butyllithium (2.50 M in hexanes, 340 muL, 0.86 mmol, 7.00 equiv) was added to astirred solution of hexamethyldisilazane (230 muL, 0.94 mmol, 7.70 equiv) in tetrahydrofuran (15mL) at 0 C. The resultant solution was warmed briefly to 23 C, then was cooled to 0 Cwhereupon a solution of 10 (50 mg, 0.12 mmol, 1 equiv) in tetrahydrofuran (5 mL) was added.The resultant mixture was stirred at 0 C for 30 min, then was cooled to -10 C whereuponN,N?-sulfuryldiimidazole (218 mg, 1.10 mmol, 9.00 equiv) was added. The reaction mixture waswarmed to 23 C and stirred at that temperature for 12 h. Excess N,N?-sulfuryldiimidazole wasquenched by the addition of methanol (5 mL), and the resultant mixture was concentrated. Theresidue was partitioned between saturated aqueous sodium bicarbonate solution (20 mL) anddichloromethane (20 mL). The layers were separated and the aqueous phase was extractedwith dichloromethane (3 ¡Á 25 mL). The combined organic layers were dried over anhydroussodium sulfate and the dried solution was concentrated. Purification of the residue by flashcolumn chromatography (20% ethyl acetate-hexanes) gave 28 (39 mg, 60%) as a colorless 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; Fash, David M.; Peer, Cody J.; Li, Zhenwu; Talisman, Ian J.; Hayavi, Sima; Sulzmaier, Florian J.; Ramos, Joe W.; Sourbier, Carole; Neckers, Leonard; Figg, W. Douglas; Beutler, John A.; Chain, William J.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 11; (2016); p. 2641 – 2644;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 822-36-6,Some common heterocyclic compound, 822-36-6, name is 4-Methyl-1H-imidazole, molecular formula is C4H6N2, 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-Fluoro-3-methoxybenzonitrile (98.2 g, 0.65 mol) was combined with 4-methyl-1 /-/- imidazole (53.4 g, 0.65 mol) and anhydrous potassium carbonate (138.2 g, 1 mol, 1.54 eq) in dimethylformamide (650 ml_), and the reaction mixture was stirred for 16 hours at 135-140 0C (internal temperature). The mixture was cooled to room temperature and filtered; the salts were washed with dichloromethane (3 x 30 ml_). The combined filtrates were evaporated in vacuo to afford a brown semisolid, which was suspended in water (500 ml_) and left to stand at 5 0C for 24 hours. The mixture was filtered, and the solid was washed with ice water (2 x 50 ml_), then dried in vacuo to afford a yellow solid (105.5 g). Crystallization from methanol (106 ml_) provided purified product (66.3 g) as yellowish crystals. These were boiled with acetone (100 ml_) for 5 minutes and the mixture was left to cool overnight. The mixture was filtered, and the crystals were washed with acetone (2 x 10 ml_) to afford the title compound as a white solid. Yield: 54.6 g, 0.256 mmol, 39%. 1H NMR (400 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.94 (s, 3H), 6.97 (m, 1 H), 7.30 (m, 1 H), 7.37 (m, 2H), 7.79 (d, J=1.4 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-1H-imidazole, its application will become more common.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, name is 5-Iodo-1H-imidazole, 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. category: imidazoles-derivatives

A mixture of 4-iodoimidazole (2.5 g, 12.89 mmol), CS2CO3 (6.3 g, 19.33 mmol) and BnBr (2.6 g, 15.47 mmol) in CH3CN (50 mL) was stirred at 80 C for 12 hrs. After being cooled to rt, the solid was filtered and the filtrate was concentrated in vacuo. The residue was purified by prep-HPLC to give l-benzyl-4-iodo-imidazole (2.68 g) as a white solid.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; WANG, Yongguang; YANG, Song; (84 pag.)WO2018/83081; (2018); 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 934-22-5 as follows. Quality Control of 6-Aminobenzimidazole

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Trityl-1H-imidazole-4-carbaldehyde

Under argon atmosphere, 8.5 ML (4.43 mmol, 1.5 equivalents) of the solution of tert-butyl bromozincacetate in tetrahydrofuran obtained in Example 59 was added dropwise to a solution of 1 g (2.96 mmol) of 1-trityl-1H-imidazol-5-carbaldehyde in 10 ML of THF at 5?9C. The mixture was stirred at 2?5C for 3 hours and 30 minutes. 10 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 15 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 5 ML of 1N hydrochloric acid, 5 ML of water, 5 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 5 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. Concentration under reduced pressure, the residue was loosened with 7 ML of IPE, filtered and washed with 7 ML of IPE. After washing, vacuum drying (40C) to a constant weight afforded 1.15 g of the desired product (yield 86%).1H NMR (CDCl3): delta 1. 4 2 (9H, s), 2.70-2.85 (2H, m), 3.52 (1H, d, J=4.8 Hz), 5.03-5.09 (1H, m), 6.79 (1H, s), 7.09-7.15 (6H, m), 7.30-7.38 (10H, m).

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 33016-47-6.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1471056; (2004); 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 50995-95-4 as follows. name: 2-Propylimidazole

EXAMPLE 19 8-(2-n-Propyl-1H-imidazol-1-yl)-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxaline-1,4(2H,5H)-dione, hydrochloride The title compound was prepared from 4-amino-2-fluoro-5-nitrobenzotrifluoride and 2-n-propylimidazole by a method analogous to the method described in example 10. M.p.>300 C. 1 H-NMR (DMSO-d6): delta0.86 (t, 3H), 1.55-1.79 (m, 2H), 2.65 (t, 2H), 7.83 (d, 1H), 7.87 (s, 1H), 7.91 (br.s, 1H), 8.82 (s, 1H), 12.44 (s, 1H), 13.30 (s, 1H).

According to the analysis of related databases, 50995-95-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Novo Nordisk A/S; US5532236; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 116989-51-6,Some common heterocyclic compound, 116989-51-6, name is 2-(2-Nitro-1H-imidazol-1-yl)ethanamine hydrochloride, molecular formula is C5H9ClN4O2, 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.

Synthesis of N1-[2-(2-nitro-1H-1-imidazolyl)ethyl]-3-iodobenzamide Into a solution of 2-(2-nitro-1H-1-imidazolyl)-1-ethylamine hydrochloride (23.3 mg) in dimethylformamide (5 mL), triethylamine (50.3 muL) and a solution of 2,5-dioxotetrahydro-1H-1-pyrrolyl-3-iodobenzoate (50 mg) in dimethylformamide (1 mL) were added, followed by stirring at room temperature overnight. After distilling off the solvent, dichloromethane was added to the residue, followed by washing with water. The resulting organic layer was dried over anhydrous sodium sulfate and after that the solvent was distilled off. The resulting residue was then dissolved in dichloromethane and impurities were filtered off to give the title compound (21.8 mg). 1H-NMR (400 MHz, DMSO-d6) delta: 3.66-3.70 (2H, m), 4.54-4.57 (2H, t, J=6.3), 7.12 (1H, t, J=0.98 Hz), 7.24-7.28 (1H, t, J=7.8 Hz), 7.52 (1H, s), 7.71-7.73 (1H, m), 7.86-7.89 (1H, m) 8.04 (1H, d). ESI-MS (m/z): 387 (M-H+)

The synthetic route of 116989-51-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM RI PHARMA CO., LTD.; US2012/219500; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem