Category: imidazoles-derivatives

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 496-46-8 as follows. Quality Control of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

Synthesis of cucurbit[n]urils in methanesulphonic acid (MSA) using paraformaldehydeUnsubstituted glycoluril (20 g) and methanesulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 90 C. Paraformaldehyde (8.45 g) was added in portion-wise and the reaction mixture was then heated to 100 C (internal) for 18 hours. The reaction mixture was cooled and added to methanol (410 ml) to produce a brown powder which was analysed by1H NMR.Approximate Yields by1H NMR (% of recovered product) cucurbit[5]uril 0%, cucurbit[6]uril 63%, cucurbit[7]uril 35%, cucurbit[8]uril 0%, cucurbit[9]uril 0%, cucurbit[10]uril 0% cucurbit[11]uril 0%.Residual formaldehyde by HPLC method was 1621 ppm.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-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. HPLC of Formula: C4H6N2S

EXAMPLE 28 A mixture consisting of 2.85 g (25 mmoles) of 1-methyl-2-mercaptoimidazole, 22 mg (0.12 mmoles) of saccharin, 20 ml of toluene and 5.2 ml (25 mmoles) of hexamethyldisilazane was refluxed for 1 hour and after cooling to room temperature, 5.40 g (25 mmoles) of 4-nitrobenzyl bromide and then 5 ml of hexamethylphosphoric triamide were added to the mixture which contained 1-methyl-2-(trimethylsilylthio)-imidazole. After stirring for 2 hours at room temperature, the mixture was diluted to 150 ml with ethyl acetate and the solution thus obtained was washed three times with 50 ml of a saturated sodium bicarbonate solution and then twice with 20 ml of water. The organic layer was dried, filtered and evaporated to dryness and the crystalline residue was washed with 100 ml of petroleum ether (boiling range 60-80 C.) and then vacuum dried to obtain 5.54 g (89% yield) of 1-methyl-2-(4-nitrobenzylthio)-imidazole melting to 74-77 C. Crystallization of a sample from ethanol raised the melting point to 77.5-78.0 C.

The synthetic route of 1-Methyl-1H-imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gist-Brocades N.V.; US4496720; (1985); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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.

General procedure: Example 2: General procedure for the preparation of compounds (IB 1-20): Cynuric chloride (1) (lOg, 54.2 mmol, 1.0 eq) was substituted by morpholine (7) (4.72 ml, 5.42 mmol, 1.0 eq) in methylene chloride (60 ml), at -50 C for 20 min to obtain intermediate (3). The intermediate (3) (5 g, 1.0 eq) on further treatment with di-substitued benzimidazole (7) (1.4 eq) in presence of K2C03 (1.44 eq) in DMF (20 ml) , at -5 C for 30 min and then at room temperature for 4 h led to intermediate (8) . To the solution of intermediate (8) (100 mg, 1.0 eq) in DMF (3 ml) are added K2C03 (1.4 eq) and substituted aryloxy piperidines (6) (1.44 eq).This resulting reaction mixture was stirred at room temperature for 24 h. The thus-obtained mixture was poured into water (30 ml) and extracted with ethyl acetate twice washed with 2N HC1 solution and dried under vacuo. This crude product was purified by silica gel column chromatography using an ethyl acetate and hexane mixture as solvent to obtained the compounds formula (1B1-20).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; THATIKONDA, Thanusha; KUMAR, Suresh; SINGH, Umed; MAHAJAN, Priya; MAHAJAN, Girish; NARGOTRA, Amit; MALIK, Fayaz; MONDHE, Dilip Manikrao; VISHWAKARMA, Ram Asrey; SINGH, Parvinder Pal; (60 pag.)WO2016/79760; (2016); 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

Adding a certain compound to certain chemical reactions, such as: 124750-59-0, name is 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester, 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 124750-59-0, Safety of 2-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester

Part B Preparation of 1-[(2′-Carbomethoxybiphenyl-4-yl)methyl]-4,5-dicarbomethoxy-2-n-propylimidazole 2-n-Propyl-4,5-dicarbomethoxyimidazole (2.00 g, 8.8 mmol, 1 eq.) was alkylated with 4′-bromomethyl-2-carbomethoxybiphenyl (2.70 g, 8.8 mmol, 1 eq.) by the procedure described in Example 1, Part A. Obtained 3.87 g of a yellow oil which was suitable for further transformation. NMR (DMSO-d6): delta7.84-7.22 (m, 4H); 7.22 (d, 2H, J=9 Hz); 7.13 (d, 2H, J=9 Hz); 5.50 (s, 2H); 3.77 (s, 3H); 3.75 (s, 3H); 3.55 (s, 3H); 2.67 (t, 2H, J=7 Hz); 1.67 (t of q, 2H, J=7,7 Hz); 0.88 (t, 3H, J=7 Hz).

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-Propyl-1H-imidazole-4,5-dicarboxylic acid dimethyl ester, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US5138069; (1992); A;,
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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1H-imidazol-2-amine sulfate(2:1)

2-Aminoimidazole sulfate (659 mg) is dissolved in 0.42 mL of concentrated HC1, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 oC. To the solution is added 345 mg of NaN02 in 1 mL of water dropwise so the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.0 g of 2,2,2-trifluoro-l-(4- pentyl-3,4- dihydroquinoxalin-l(2H)-yl)ethan-l-one, 0.82 g of sodium acetate and 3 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and brick red solid is collected. The crude (E)-l-(7-((lH-imidazol-2-yl)diazenyl)-4-pentyl-3,4- dihydroquinoxalin-1 (2H)-yl)-2,2,2-trifluoroethan-l -one is dried and used in the next step without further purification (0.94 g).

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOXELL CORPORATION; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (106 pag.)WO2018/53034; (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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., name: 1H-Imidazole

(1) will nitroiodobenzene 0.248g (1.0mmol), imidazole 0.069g (1.0mmol), Cu (OAc)2·H2O 0.030g (0.15mmol), 2,2- biimidazole 0.022g (0.15mmol), cesium carbonate 0.652g (2mmol), DMSO (2mL) was added the reaction tube with a piston, was heated to 80 deg.] C with stirring for 48 hours reaction.(2) TLC until the reaction was complete the reaction was followed ends.After the reaction was cooled to room temperature, diluted with water, extracted with ethyl acetate 3-4 was added, and the combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product.After the end of (3) to obtain the crude product was purified by column chromatography (petroleum ether / ethyl acetate elution) to give the desired product 13 (yield 86%).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Soochow University (Suzhou); Zeng Runsheng; Zhou Chunmei; Zou Jianping; (15 pag.)CN104447557; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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. Recommanded Product: 1,1′-Thiocarbonyldiimidazole

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL of CH2Cl2 at RT was added 6.4 g (35 mmol) of 1,1?-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy-phenyl)-methyl-propyl-amine (6) (7.85 g, 95%) as a colorless oil.

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

Reference:
Patent; Synta Pharmaceuticals Corp.; Du, Zhenjian; Foley, Kevin Paul; US9108933; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, 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 1402838-08-7, Recommanded Product: 2-(1-Trityl-4-imidazolyl)benzaldehyde

A slurry of tert-butyll-oxo-7-azaspiro [3.5jnonane-7-carboxylate (2.27 g, 9.49 mmol), 2-[1-(triphenylmethyi)-l H-imidazol-4-yl]benzaldehyde (4.04 g, 9.74 mnioi) and Ca(OH)2 (2.10 g, 28.33 mmol) in EtOH (100 mL) were mixed and stirred overnight at 80 C. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 7.4 g (crude) of tert-butyl(2E)-1 -oxo-2-([2-[ I -(tripbenylmethyl)-IN-imidazol-4-yI] phenyljmethylidene)-7- azaspiro[3.5]nonane-7-crboxy1ate as a yellow solid. LCMS (ESI) rniz 636.2 [M+HJ

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1-Trityl-4-imidazolyl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; PEI, Zhonghua; PASTOR, Richard; GAZZARD, Lewis; PARR, Brendan; LIU, Wendy; MENDONCA, Rohan; WU, Guosheng; YUEN, Po-Wai; (183 pag.)WO2019/5559; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The chemical industry reduces the impact on the environment during synthesis 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem