Author: Jessica.F

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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41716-18-1

To a solution of 1-methyl-1Himidazole-4-carboxylic acid (0.50 g, 4.0 mmol), 1-hydroxybenztriazole monohydrate (0.74 g, 4.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) in acetonitrile (10 mL) was added a solution of 3-(trifluoromethoxy) benzylamine 8(0.84 g, 4.4 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo, and saturated aqueous NaHCO3solution was added to the residue. After extraction with ethyl acetate, the organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (0?10percent MeOH in CHCl3) to obtain 9(1.18 g, 98percent) as a colorless powder.1H-NMR (600 MHz, CDCl3) delta: 3.73 (3 H, s), 4.62 (2 H, d, J=6.0 Hz), 7.08?7.13 (1 H, m), 7.18 (1 H, s), 7.26?7.29 (1 H, m), 7.31?7.37 (2 H, m), 7.44?7.51 (1 H, m), 7.55 (1 H, d, J=1.4 Hz); MS ESI: m/z300 [M+H]+.

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 41716-18-1.

Reference:
Article; Yamamoto, Shuji; Ohta, Hiroshi; Abe, Kumi; Kambe, Daiji; Tsukiyama, Naohiro; Kawakita, Yasunori; Moriya, Minoru; Yasuhara, Akito; Chemical and Pharmaceutical Bulletin; vol. 64; 11; (2016); p. 1630 – 1640;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 57090-88-7, 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 57090-88-7 as follows.

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.5 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil. Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H). found 224.1.

According to the analysis of related databases, 57090-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; Meegalla, Sanath K.; Rudolph, M. Jonathan; Wall, Mark J.; Wilson, Kenneth J.; Desjarlais, Renee L.; Manthey, Carl L.; Molloy, Christopher J.; US2008/51402; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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 stirred mixture of intermediate 62 (120 mg, 0.32 mmol), 2-oxo-2,3-dihydro-1Hbenzo[d]imidazole-S-carbaldehyde (CAS: 106429-59-8) (104 mg, 0.64 mmol) and TiG-PrO)s (92 mg, 0.32 mmol) in DCE/DMSO(6 mL/2 mL) at 0 C was added NaBH(OAc); (205 mg, 0.97 mmol) in portions. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with aq. NaHCOsand the resultant was extracted with DCM. The combined organic extracts were washed with brine, dried over anhydrous Na2SQOuq,filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H,O (0.1% TFA), B: ACN) to give Compound 117 (22 mg TFA salt, yield: 13%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Formula: C4H6N4O2

In a 1,000-liter reactor was charged 320 kg of water, Heated to reflux, 71 kg of glycoluril and 58 kg of 50% glyoxal were successively added, Stirring to clear, In the refluxing state, 500 L of a sodium hydroxide solution (8 mol / l) was rapidly added dropwise, After completion of the dropwise addition, The refluxing reaction was continued for 8 hours. Close the heating,When the temperature naturally cool to room temperature,45 kg of chlorine gas was introduced into the reaction system,After completion of the reaction,Concentrated hydrochloric acid was added to adjust the pH to 1,Stirring was reduced to room temperature,After 2 hours,Obtain crude orotic acid.In the 2000-liter reactor, the crude orotate was added and 600 kg of water was added. After boiling, add the concentrated ammonia to dissolve, then add 5 mol / L sulfuric acid to adjust the pH to weak acidity, add activated carbon to boil for 30 minutes, filter it hot, adjust the pH to 1 with concentrated sulfuric acid, Dry, get whey acid finished 25.7 kg, yield 33%, purity 99.9%.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Baishixing Science and Technology Industry Co., Ltd.; Shi, Changqing; (6 pag.)CN106187918; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13435-22-8,Some common heterocyclic compound, 13435-22-8, name is 1-Butyl-2-methyl-1H-imidazole, molecular formula is C8H14N2, 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.

Ex is of a 1-butyl-2-methyl-3(propyl-3-sulfonyl) imidazolium 1-Butyl-2-methylimidazol (710 mg, 0.9 mmol, 1 equivalent) was dissolved in 10 ml toluene and propanesultone (610 mg, 0.9 mmol, 1 equivalent) was added. The clear solution was heated at reflux temperature for 3h at which time a some withe precipitate was formed. The reaction mixture was cooled to room temperature and the white suspension was then filtered and washed with 5 ml toluene. The white solid was dried under high vacuum at 60C for 4 h, yielding the desired product (89 mg, 38% yield). H NMR analysis confirms the structure and a purity of >98 %. Melting point by DSC: 160 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Butyl-2-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; ECOLE D’INGENIEURS ET D’ARCHITECTES DE FRIBOURG; MARTI, Roger; VANOLI, Ennio; AEBY, Sandrine; FISCHER, Fabian; HAPPE, Manuel; WO2013/8172; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13275-42-8, The chemical industry reduces the impact on the environment during synthesis 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, Cu(OAc)2 (18 mg, 0.1 mmol, 20 mol%), NaOEt (68 mg, 1.0 mmol), 1,10-phenanthroline monohydrate (40 mg, 0.2 mmol, 40 mol%), 2-(2-bromophenyl)-1H-benzo[d]imidazole 4 (0.5 mmol), and N-heterocycle 2 (0.5 mmol). The Schlenk tube was evacuated and backfilled with O2 (this procedure was repeated three times). Under a counter flow of O2, DMF (2.0 mL) was added using a syringe. The reaction mixture was stirred at 140 C for 24 h. After the reaction was completed, the mixture was extracted with dichloromethane (3 × 15 mL), and then the organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Subsequently, the solvent was removed, and the product was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol as the eluent, affording the pure products

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-(2-Bromophenyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Dingben; Huang, Ling; Yang, Jianguo; Ma, Junna; Zheng, Yingying; Luo, Yi; Shen, Yang; Wu, Jiashou; Feng, Chao; Lv, Xin; Tetrahedron Letters; vol. 59; 21; (2018); p. 2005 – 2009;,
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

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

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

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