Category: 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. HPLC of Formula: C3HBr3N2

PRODUCTION EXAMPLE 3 [PRODUCTION OF THE PRESENT COMPOUND (3)] To a solution of a sodium salt, prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 1.23 g of 4-bromobutoxymethyl bromide at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the reaction mixture which was then extracted with three 30-ml portions of ether. The ether layer was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel to obtain 0.74 g of 1-(4-bromobutoxymethyl)-2,4,5-tribromoimidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2034-22-2, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US4689340; (1987); A;,
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 2034-22-2 as follows. Safety of 2,4,5-Tribromoimidazole

Step 1: N-(2.4.5-tribromo-l-(r2-(trimethylsilv?ethoxy1methyl|-lH-imidazole (A1); To a solution of 2,4,5-tribromo-imidazole in THF was added portionwise sodium hydride (1 eq.). The mixture was stirred for 20 min at RT and SEM-Cl (1 eq.) was added. The mixture was left stirring for 16 h at RT. After dilution with Et2O the suspension was filtered and the clear solution was concentrated to dryness under reduced pressure. The oily residue was dissolved in PE/ 5% EtOAc and applied on a silicagel column. After washing with PE/ 5% EtOAc the product was eluted with PE/ 10% EtOAc. The solvents were removed under vacuum to afford the title compound as a white solid. 1U NMR (400 MHz, CDCl3) delta: 5.31 (s, 2H), 3.59 (t, J=7.8 Hz, 2H), 0.92 (t, J=7.8 Hz, 2H), 0.01 (s, 9H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2008/56187; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-22-2, 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 2034-22-2 as follows.

Preparation 15-Bromo-2-ethoxy-3H-imidazole-4-carbaldehyde 2,4,5-Tribromo-1H-imidazole (1a) (98.7 g, 324 mmol, 1.0 eq) was dissolved into 1.20 L of DCM and cooled to 0 C. To this was added DIPEA (62 mL, 360 mmol, 1.1 eq) followed by the slow addition of [beta-(trimethylsilyl)ethoxy]methyl chloride (60.2 mL, 340 mmol, 1.05 eq). The solution was slowly warmed to room temperature. After 2 hours the mixture was washed with 1M H3PO4/saturated aqueous NaCl (1:10; 2×600 mL). The organic layer was dried over MgSO4, and evaporated to dryness, yielding intermediate (1b) as faint yellow liquid that solidified on standing (137 g).Intermediate (1b) (130 g, 290 mmol, 1.0 eq) was dissolved into anhydrous EtOH (650 mL). To this was slowly added potassium t-butoxide (98.6 g, 879 mmol, 3.0 eq) and the mixture was heated to reflux for 16 hours. The mixture was then cooled to room temperature, filtered and concentrated. The resulting oil was dissolved in EtOAc (800 mL) and washed with saturated NaHCO3 (400 mL). The layers were separated and the organic was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated, yielding intermediate (1c) as a brown oil (115.3 g). MS m/z: [M+H+] calcd for C11H20Br2N2O2Si, 401.9 found 401.2.Intermediate (1c) (69.5 g, 174 mmol, 1.0 eq) was dissolved in anhydrous THF (600 mL) and cooled to -78 C. under nitrogen. A 2.5M solution of n-butyllithium in hexanes (72.9 mL, 180 mmol, 1.05 eq) was added dropwise and the mixture was stirred at -78 C. for 10 minutes. DMF (40 mL, 520 mmol, 3.0 eq) was then added and the mixture was stirred at -78 C. for 15 minutes and was then warmed to room temperature. The reaction was quenched with water (10 mL), diluted with EtOAc (600 mL) and was washed with water (100 mL), saturated aqueous NaCl, dried over MgSO4 and concentrated under reduced pressure. The recovered material was purified by silica gel chromatography (15-30% EtOAc:hexanes) to produce intermediate (1d) as a pale yellow oil (45 g).Intermediate (1d) (105.8 g, 303 mmol, 1.0 eq) was cooled at 0 C. in ice. TFA (300 mL) was added and the mixture was stirred at 0 C. for 15 minutes, then warmed to room temperature. After 90 minutes the mixture was concentrated under reduced pressure and redissolved in EtOAc (700 mL). The organic was washed with saturated bicarbonate (2×600 mL), saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure to produce a yellow solid. The material was suspended in hexanes (300 mL) and stirred at 0 C. for 30 minutes. The material was filtered and the solid was washed with cold hexanes (150 mL) to yield the title compound as a pale white solid (61.2 g). 1H-NMR (CDCl3) delta (ppm): 1.4 (m, 3H), 4.5 (m, 2H), 5.2 (s, 1H), 9.2 (d, 1H).

According to the analysis of related databases, 2034-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chao, Robert S.; Zhang, Weijiang; US2010/81697; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2, A common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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 dried 500 mL round bottom flask was charged with 2,4,5-tribromoimidazole (20.0 g, 65.62 mmol) and anhydrous DMF (100 mL), the resulting solution was cooled to 0 C. To this cold solution was added NaH (60% in mineral oil, 2.80 g, 70.0 mmol) portionwise with gas evolution under control and an internal temperature maintained below 10 C. After addition, the cold bath was removed and the resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was cooled back to 0 C., and SEM chloride (12.2 mL, 69.5 mmol) was added to the reaction via syringe pump over 30 minutes. The reaction was stirred at 0 C. for an additional 30 minutes and at ambient temperature for another 30 minutes. The reaction was deemed complete by LCMS and the mixture was partitioned between EtOAc (150 mL) and water (300 mL), and the layers separated. The organic phase was sequentially washed with dilute aqueous NaCl (5% w/w, 2*), then brine (100 mL), dried (Na2SO4), concentrated and a light yellow solid was obtained. The crude material was recrystallized from hot petroleum ether (30 mL) and the solids were harvested from the mother liquor at 0 C. The product was washed with cold petroleum ether (30 mL) and dried under vacuum to afford 2,4,5-tribromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (26.3 g, 92% yield): 1H NMR (400 MHz, CDCl3) delta 5.31 (s, 2H), 3.59 (t, J=7.2 Hz, 2H), 0.92 (t, J=7.2 Hz, 2H), -0.01 (s, 9H, -Si(CH3)3).

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

Reference:
Patent; Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng; US2013/210818; (2013); 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. 2034-22-2, name is 2,4,5-Tribromoimidazole, A new synthetic method of this compound is introduced below., Formula: C3HBr3N2

dimethyl sulfoxide (300 mL) suspension of (2S)-2-{[4-(methoxy)phenoxy]methyl}oxirane (10.9 g), 2,4,5-tribromo-1H-imidazole (14.3 g) and cesium carbonate (18.4 g) was stirred for 4 hours at 130C . The reaction mixture was allowed to cool to room temperature, after the addition of water and ethyl acetate, the organic layer was separated and the water layer. The aqueous layer was extracted twice with ethyl acetate, combined organic layer, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (Reveleris, mobile phase: hexane / ethyl acetate = 90/10 ~ 50/50; v / v) to give the title compound (Intermediate 1: 4.73 g, pale yellow oil) was obtained .

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; TAISHO PHARMACEUTICAL CO LTD; URABE, HIROKI; NISHIKAWA, RIE; TAMIDA, TOMOKO; HATTORI, NOBUTAKA; SAKAGAMI, KAZUNARI; MATSUDA, YOHEI; YASUHARA, AKITO; (67 pag.)JP2015/6994; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2, A common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

6.02.05.01 (2,4,5-tribromo-imidazol-1-yl)-acetic acid methyl ester 5.1 mL methyl bromo acetate was added to 15 g 2,4,5-tribromoimidazole and 20.4 g potassium carbonate in 100 mL DMF. The reaction was stirred 3 h at RT. The mixture was added to water. The precipitate was filtered, washed with water and dried to give 18.1 g desired product. Rt: 0.93 min (method B), ESI+: 375

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

Reference:
Patent; RUDOLF, Klaus; BISCHOFF, Daniel; DAHMANN, Georg; GRAUERT, Matthias; KUELZER, Raimund; US2013/150355; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2, 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. 2034-22-2, name is 2,4,5-Tribromoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a reaction flask were added 2,4,5-tribromo-1H-imidazole 9(3 g,10 mmol), sodium sulfite (6.3 g, 50 mmol) and 30 mLwater andthen heated at 110 C for 6 h. After cooling to room temperature, theproduct precipitated as a yellowish solid was filtered and theaqueous phase was extracted by ethyl acetate (3 30 mL). Thecombined organic extracts were washed with water (3 30 mL)and dried over anhydrous magnesium sulfate. Ethyl acetate wasremoved by rotary evaporator and yellowish solid 10 was obtained(1.25 g, 85% yield); mp: 131-132.5 C (lit. mp 130-131 C) [43].

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shirvani, Pouria; Fassihi, Afshin; Saghaie, Lotfollah; Van Belle, Siska; Debyser, Zeger; Christ, Frauke; Journal of Molecular Structure; vol. 1202; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-22-2, 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. 2034-22-2, name is 2,4,5-Tribromoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a single-necked flask was added 2,4,5-tribromoimidazole (49 g, 161 mmol)Sodium sulfite (101.5 g, 806 mmol)And water (500 ml) were added and stirred at 110 C for 6 h,Ethyl acetate was added,The organic layers were combined and dried over anhydrous sodium sulfate,Rotate the ethyl acetate to give compound 6 (20.5 g, yield 89%)

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, 2,4,5-Tribromoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hinova Pharmaceuticals Inc.; Fan, Lei; Chen, Ke; Li, Xinghai; Chen, Yuanwei; (24 pag.)CN106256830; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-22-2, 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. 2034-22-2 name is 2,4,5-Tribromoimidazole, 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.

Step 1. 2,4,5-Tribromo-l-methyl-lH-imidazole (0975) [00314] To a suspension of sodium hydride (0.787 g, 19.69 mmol) in DMF (15 mL) was added 2, 4, 5-tribromo-lH-imidazole (5 g, 16.41 mmol) in DMF (10 mL) at ambient temperature. The mixture was stirred at 50 C for 1 h, cooled to 0 C, and treated with methyl iodide (1.128 ml, 18.05 mmol). The mixture was warmed to 50 C and stirred 16 h, the DMF was removed under reduced pressure and EtOAc was added. The mixture was washed with water, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (eluting with a gradient of 10-80% EtOAc/hexanes) afforded 4.87 g (94%) of 2,4,5-tribromo-l -methyl- lH-imidazole. 1H MR (300 MHz, CDC13) delta 3.62 (s, 3H). MS (ESI) m/z 316.77 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Tribromoimidazole, and friends who are interested can also refer to it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2034-22-2, 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. 2034-22-2, name is 2,4,5-Tribromoimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure for the synthesis of AB1 To a stirred solution of 2,4,5-tribromoimidazole (1.0 g, 3.28 mmol) in tetrahydrofuran (15.0 mL) was added NaH (60% dispersion in paraffin, 0.20 g, 4.92 mmol) under ice-bath. After 10 min, chloromethyl methyleter (0.30 mL, 3.94 mmol) was added slowly. The reaction mixture was allowed to room temperature and further stirred for 1.5 hours. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (20 mL x 2). The organic layer was dried over anhydrous MgS04 and concentrated in vacuo to give AB1.

The synthetic route of 2,4,5-Tribromoimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSTITUT PASTEUR KOREA; TERRAMARK MARKENCREATION GMBH; KIM, Jaeseung; KANG, Sunhee; KANG, Juhee; LEE, Sumi; SEO, Jeong Jea; SEO, Mooyoung; (156 pag.)WO2015/193506; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem