Category: imidazoles-derivatives

Synthetic Route of 1792-40-1, 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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

(95a) Using conditions analogous to (1f), 2-methyl-5-nitro-benzimidazole (101 mg, 0.568 mmol) was reacted with methyl 4-(bromomethyl)-benzoate to provide the desired ester (71 mg, 40%). MS found: (M+H)+=326.

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-5-nitro-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ott, Gregory R.; Chen, Xiao-Tao; Duan, Jingwu; Lu, Zhonghui; US2003/139388; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 714273-83-3, These common heterocyclic compound, 714273-83-3, name is 5-(tert-Butyl)-1H-imidazole-4-carbaldehyde, 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.

5 g (32.85 mmol) of 5-(tert-butyl)-1H-imidazole-4-carbaldehyde was added to 35 mL of DMF,An additional 13.02 g (65.7 mmol) of N,N’-diacetylpiperazine-2,5-dione nitrogen was added to protect the exhaust, and 16.05 g (49.28 mmol) of cesium carbonate was added to protect the exhaustThe reaction was stirred at room temperature in the dark for 20 h. The reaction solution was poured into 500 mL of ice water and suction filtered.The filter cake was washed with water (100 mL * 2), petroleum ether: ethyl acetate = 8: 1 (400 mL),The filter cake was dispersed ultrasonically with ethanol and dichloromethane, insoluble matter was filtered off, and concentrated under reduced pressure.Anhydrous ethanol with water. It was further slurried with ethyl acetate (200 mL) to obtain a brown-yellow solid. Get 4.05 g of (Z)-1-acetyl-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione, Yield: 42%.

The synthetic route of 714273-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsingtao Ocean Bio-pharmaceutical Institute Co., Ltd.; Li Wenbao; Fu Zhangyu; Hou Yingwei; Ji Cunpeng; Wang Shixiao; Ma Mingxu; Guan Huashi; (21 pag.)CN110240592; (2019); A;,
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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C4H4N2O

A reaction mixture with 3-amino-lH-pyrrole-2-carboxylic acid ethyl ester (0.2 g, 1.30 mmol), 2-imidazolecarboxaldehyde (0.15 g, 1.53 mmol), NaCNBH3 (0.082 g, 1.30 mmol) EPO and OHAc (0.15 mL, 2.60 mmol) in methanol (5 mL) was stirred at r.t. for 2 h. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. Washed with water and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.30 g (99%) of the title compound.1H NMR (DMSO-d6) delta ppm 10.84 (IH, br s), 7.03 (2H, s), 6.79 – 6.64 (IH, m), 5.76 (IH, br s), 5.68 – 5.57 (IH, m), 4.29 (2H, d, J=5.8 Hz), 4.19 (2H, q, J=7.1 Hz), 3.16 (IH, s), 1.26 (3H, t, J=7.1 Hz); MS (ESI) m/z 235 (M +1).

The synthetic route of 10111-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/62465; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, 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 1457-58-5, Safety of 2-Methyl-1H-imidazole-5-carboxylic acid

Intermediate 661 -(2-Fluoro-4-methanesulfonylphenyl)-2-methyl-1 H-imidazole-4-carboxylic acidA mixture of 2-methyl-1 H-imidazole-4-carboxylic acid (500 mg), N,N-diisopropyl- ethyl-amine (4 mL), and 1 ,2-difluoro-4-methanesulfonylbenzene (1 .2 g), in N,N- dimethylformamide (6 mL) is heated to 120 C overnight. The crude product is purified by HPLC. LC (method 20): tR = 0.90 min; Mass spectrum (APCI): m/z = 299 [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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; HECKEL, Armin; HIMMELSBACH, Frank; LANGKOPF, Elke; NOSSE, Bernd; ASHWEEK, Neil, J.; HARRIOTT, Nicole; WO2012/168315; (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. 53981-69-4, name is 1-(1H-Imidazol-2-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1H-Imidazol-2-yl)ethanone

To a mixture of l-(l /-imidazol-2-yl) ethan-l-one (32 mg, 0.290 mmol) and 2-(4- formylphenyl)-N-(perfluorophenyl) acetamide (124 mg, 0.377 mmol, 1.3 eq) in a microwave vial under nitrogen were added piperidine (61 mu, 0.726 mmol, 2.5 eq) and anhydrous methanol (5.0 mL) via syringe. The reaction mixture was heated in the microwave synthesizer for 5 h and it was monitored by TLC (50% ethyl acetate/hexanes). Methanol was removed on a rotary evaporator to obtain a brown oil. It was chromatographed by preparative TLC in 50-75% ethyl acetate /hexanes to obtain (£)-2-(4-(3-(l /-imidazol-2-yl)-3-oxoprop- l-en-l-yl) phenyl)-N-(perfluorophenyl) acetamide 35 as a brown solid (16 mg, 13.07%). TLC R/ = 0.5 (50% ethyl acetate/hexanes), mp 235 C. NMR (600 MHz, CD3OD) delta 7.94 (s, 1H), 7.92 (s, 2H), 7.89 (s, 2H), 7.86 (s, 1H), 7.75 (d, J = 8.1 Hz, 6H), 7.46 (d, J = 8.0 Hz, 6H), 7.41 (s, 3H), 7.29 (s, 3H), 3.83 (s, 7H). 13C NMR (151 MHz, MeOD) delta 178.61, 170.86, 166.79, 145.98, 140.81, 137.75, 133.73,130.15,129.59,128.66 ,121.42120.82,41.70 ppm. HRMS calcd for C20H14F5N3O2 :423.10 found: 423.1146

The synthetic route of 53981-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF TOLEDO; TILLEKERATNE, Viranga; AL-HAMASHI, Ayad; DLAMINI, Samkeliso; ALQAHTANI, Abdulateef, Saeed; KARAJ, Endri; (69 pag.)WO2019/36607; (2019); 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. 92507-97-6, name is 1-ethyl-2,3-dimethylimidazolium chloride, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-ethyl-2,3-dimethylimidazolium chloride

Example 181-Ethyl-2,3-dimethylimidazolium cyanodifluoropentafluoroethylborate-[C7H13N2][C2F5BF2(CN)] Potassium cyanodifluoropentafluoroethylborate K[C2F5BF2(CN)] (4.2 g, 18.0 mmol) is taken up in deionised water (2 ml), and a solution of 1-ethyl-2,3-dimethylimidazolium chloride [EDMIM]CI (3.2 g, 19.9 mmol) in 3 ml of deionised water is added. The ionic liquid obtained is washed with deionised water (4×2 ml), separated off and dried at 50 C. in vacuo. The yield of 1-ethyl-2,3-dimethylimidazolium cyanodifluoropentafluoroethylborate, which is liquid at room temperature, is 5.1 g (15.9 mmol), 88%, based on the potassium cyanodifluoropentafluoroethylborate K[C2F5BF2(CN)] employed. The product is analysed by means of ion chromatography and has low levels of contamination with halide; chloride: 7 ppm, bromide: 16 ppm, fluoride: 14 ppm. Water content (Karl Fischer titration): 161 ppm. Dynamic viscosity (20 C.): 47.2 mPa·s.Raman spectroscopy: v (CN)=2209 cm-1 1H-NMR: delta, ppm=7.60 d (CH, 1H), 3JH,H=2.15 Hz; 7.55 d (CH, 1H), 3JH,H=2.15 Hz; 4.32 q (CH2, 2H), 3JH,H=7.30 Hz; 3.90 s (CH3, 3H); 2.75 s (CH3, 3H); 1.46 t (CH3, 3H), 3JH,H=7.30 Hz.13C{1H}-NMR (cation): delta, ppm=145.32 s (Ctert, 1C); 123.30 s (CH, 1C); 121.19 s (CH, 1C); 44.20 s (CH2, 1C); 35.35 s (CH3, 1C); 15.07 s (CH3, 1C); 9.46 s (CH3, 1C).11B-NMR: delta, ppm=-2.7 tt (1B), 1JF,B=51.0 Hz, 2JF,B=25.3 Hz.19F-NMR: delta, ppm=-83.3 t (CF3, 3F), 4JF,F=5.2 Hz; -136.3 q (CF2, 2F), 2JF,B=23.3 Hz; -167.2 qq (BF2, 2F), 1JF,B=51.1 Hz, 4JF,F=5.1 HzElemental analysis: found, %, C, 37.57; H, 3.84; N, 13.10; calculated for C10H13BF7N3, %, C, 37.65; H, 4.11; N, 13.17.

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 92507-97-6.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/309981; (2012); 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. 26663-77-4, name is Methyl benzimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl benzimidazole-5-carboxylate

To a solution of methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).

According to the analysis of related databases, 26663-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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 39021-62-0, COA of Formula: C5H6N2O

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 10.6 mL, 13.8 mmol) was added dropwise by syringe to a solution of 4-bromo-2-(trifluoromethyl)pyridine (3.12 g, 13.8 mmol) in dry THF (50 mL) at 0 C. After 30 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.38 g, 12.5 mmol) in THF (28.5 mL) was added to the Grignard solution by syringe at 0 C. The reaction mixture was warmed to room temperature over 2 hours after which it was quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound.

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, 1-Methyl-1H-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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

6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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. SDS of cas: 6160-65-2

INTERMEDIATE 45Methyl 3-(f(35r)-4-(aminocarbonothioyl)mophiholin-3-yllmethyl|-l-methyl-lH-indole-5- carboxylateTo a stirred slurry of Intermediate 44 (31.64 g, 109.7 mmol) in TetaF (221 mL) at r.t. was added l,r-thiocarbonyldiimidazole (21.51 g, 120.7 mmol) portionwise over 10 minutes. The reaction mixture was stirred at r.t. for 5 h, then transferred to a pressure vessel and NH3 (111 mL of a 28% aqueous solution, 1.6 mol) was added. This mixture was stirred at 600C for 17 h, then cooled to r.t. It was diluted with water (158 mL) and solid product was filtered off, washed with water and dried in vacuo at 450C, to give the title compound (37.79 g, 99.1%) as a white solid. LCMS (ES+) 348.0 (M+H)+, RT 2.88 minutes (Method I).

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2009/71895; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 939-70-8,Some common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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: A 10%solution of NaOH (5 ml) in EtOH was added to a solutionof 2-acetylbenzimidazole (4) (1.6 g, 0.01 mol) in absoluteEtOH (20 ml) at 0C with stirring. Then the solution of anaromatic aldehyde (0.01 mol) in absolute EtOH (10 ml)was added dropwise. The reaction mixture was stirred for12 h at room temperature. After completion of reaction(monitored by TLC), the reaction mixture was poured ontocrushed ice. The separated solid was filtered off, washedwith water, and dried. The residue was purified by columnchromatography (silica gel, eluent 10% ethyl acetate inpetroleum ether) to afford pure benzimidazole-derived chalcone 5a-m.

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

Reference:
Article; Meshram, Gangadhar A.; Vala, Vipul A.; Chemistry of Heterocyclic Compounds; vol. 51; 1; (2015); p. 44 – 50; Khim. Geterotsikl. Soedin.; vol. 51; 1; (2015); p. 44 – 50,7;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem