Category: imidazoles-derivatives

Reference of 152628-02-9, 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

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

Electric Literature of 32673-41-9, 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. 32673-41-9 name is 4-Imidazolemethanol hydrochloride, 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.

538 mg starting material (4 mmol) was dissolved in ~ 4 ml methanol and 500 mg NaHCO3 (6 mmol) was added. The tube was occasionally stirred for 60 min, alternatively at 4 C and at warm water temperature. CO2 was allowed to escape from the glass tube. The mix was divided across several Eppendorf tubes and subjected to Speedvac treatment for 1 hour. Residues were white solids with light-yellow sirupy liquids. Chloroform/methanol mix 1:1 was added to the tubes with subsequent gentle warming and stirring. NaHCO3 was separated by centrifugation of the combined fractions at 3500 rpm for 5 min. Clear supernatant was kept overnight at -20 C to allow the precipitation of additional NaHCO3. Then, the solution was cleared by filtration and evaporated to dryness with a Rotavapor device. The residue was taken up in 20 ml dioxane with magnetic stirring and 4.4 mg MnO2 (activated; for synthesis) was added in the same flask. The residue may not have been dissolved completely in first instantion. The mix was refluxed for 2 hours on a paraffin oil bath. The warm solution was filtered and MnO2 was washed once with warm dioxane. Dioxane was evaporated with the Rotavapor yielding a white and yellow fine cristalline solid. Crystallization was carried out in methanol repeated times. Small volumes of methanol were required, because the residue dissolved well in methanol

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

Reference:
Patent; Academisch Ziekenhuis bij de Universiteit van Amsterdam; EP1196129; (2005); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113775-47-6, name is Dexmedetomidine, 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 113775-47-6, Safety of Dexmedetomidine

20 g (100 mmol) of 4- [1- (2,3-dimethylphenyl) ethyl] -1H-imidazole and 9 g (70 mmol) of L – (+) – tartaric acid were added to 80 ml of absolute ethanol,Heated to 65 stirring,After the reaction was dissolved to continue stirring for two hours,Then cooled to 10 C,Stir overnightAt this time a large number of white solid,Suction filtration,The filter cake was washed with absolute ethanol,Get dexmedetomidine tartrate 16.6g,Yield 47.3%The ee value is 99.24%.

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; Tsingtao Chenda Biological Technology Co., Ltd.; Lv Yanhua; (8 pag.)CN106588778; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5805-57-2, 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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To 8-(benzyloxy)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-5-yl trifluoromethanesulfonate (128 mg) and 2-(aminomethyl)benzimidazole (131 mg), triethylamine (86 muL) and dioxane (12 mL) were added, and the mixture was heated with stirring at 60 to 70C for 3 hours and 45 minutes. After cooling of the reaction mixture, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-80% chloroform/methanol] and then suspended in a mixed solvent of 2-propanol and diisopropyl ether, and the deposit was collected by filtration to obtain a pale yellow solid of 5-(((1H-benzimidazol-2-yl)methyl)amino)-8-(benzyloxy)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (6 mg). 1H-NMR (DMSO-d6) delta value: 3.10 (s, 3H), 4.68-4.76 (m, 2H), 5.07 (s, 2H), 5.56 (s, 1H), 7.00-7.80 (m, 10H), 8.93 (s, 1H).

The synthetic route of (1H-Benzo[d]imidazol-2-yl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toyama Chemical Co., Ltd.; KAWAI, Hyouei; MURATA, Daigo; SUZUMURA, Yuko; EP2810944; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 95470-42-1, 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 95470-42-1 as follows.

After the addition of K2CO3(1.05 g, 7.63 mmol) thereto, a solution of 2-bromo-4-methyl-lH-imidazole-5-carboxylic acid ethyl ester (1.2 g, 5.08 mmol) in DMF (45 ml) was stirred at room temperature for 30 min and mixed with benzyl chloride (0.7 ml, 6.10 mmol). The reactants were induced to react therewith by elevating the temperature to 120¡ãC with stirring for 8 hrs. After the completion of reaction, the reaction mixture was cooled and added with water. Then, extraction with ethyl acetate was precedent to drying over MgSO4, followed by filtration and vacuum concentration. Through silica gel column chromatography (hexane : ethyl acetate = 8:1), the concentrate thus obtained was purified to the object compound as a white solid (1.06 g, 3.28 mmol, 65percent) . 1H-NMROOO MHz, CDCl3) sigma 1.40 (t, 3H, J = 7.1 Hz) , 2.48(s, 3H) , 4.37(q, 2H, J = 7.1 Hz) , 5.17(s, 2H) , 7.03 (m, 2H) , 7.32 (m, 3H) ;MS 323 (M+) .

According to the analysis of related databases, 95470-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/111794; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 53710-78-4, The chemical industry reduces the impact on the environment during synthesis 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3¡Á50mL). The combined organic phase was washed with brine (3¡Á150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/ 20 methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

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-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1615-14-1, The chemical industry reduces the impact on the environment during synthesis 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, I believe this compound will play a more active role in future production and life.

The mixture of 1-(2-hydroxyethyl)imidazole (2 g, 0.017 mol)and 1-chlorododecane (4.2 g, 0.02 mol) was stirred at 140 C for24 h under an argon atmosphere. The obtained semi-solid productwas purified bywashing with hexane-ethyl acetate mixture (4:1 (v/v), 3 30 ml). Residual solvents were removed in vacuum10 mbar at 70e80 C for 12 h. The ionic liquid has melting point of28e29 C.1H NR (400 Hz, DMSO-D6): d 0.85 (t, 3H, CH3), 1.25 (m,18H, H3(CH2)9),1.79 (m, 2H, NCH2CH2), 3.38 (br s,1H, OH), 3.72 (m,2H, NCH2CH2OH), 4.16e4.23 (m, 4, NCH2), 7.78 (br s, 1H, C4eH),7.81 (br s, 1H, C5eH), 9.27 (s, 1H, C2eH).

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-(1H-Imidazol-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Trush, Maria M.; Semenyuta, Ivan V.; Vdovenko, Sergey I.; Rogalsky, Sergiy P.; Lobko, Evgeniya O.; Metelytsia, Larisa O.; Journal of Molecular Structure; vol. 1137; (2017); p. 692 – 699;,
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. 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5805-57-2

General procedure: The receptors were prepared as follows: Tom-phthaloyl chloride (4 mmol) solution indichloromethane, was added benzimidazolederivatives (8.1 mmol) with catalytic amount oftrimethylamine under ultrasonication irradiation andstirred for 20-30 min at room temperature. Thereaction progress was examined by thin filmchromatography using solvent system, (8:2) pet ether:ethyl acetate. After completion of reaction, asmonitored by TLC, the reaction mixture was pouredinto a saturated sodium bicarbonate solution, filteredand washed with water (3×50 mL) to afford thedesired dipodal products (RA-RD). N,N’-Bis-(IH-benzoimidazol-2-ylmethyl)-isophthalamide(RA): M. pt.: 188 C. Yield: 88.1%. FTIR (KBr,v cm-1): 3259 (N-H), 3010 (aliphatic C-H), 1645(C-O). IH NMR (DMSO-d6, 400 MHz, ppm) d 4.70(2H, s, CH2), 7.12-7.47 (m, IlH, aromatic C-H), 8.06(s, IH, phenyl C-H), 8.50 (s, 2H, amide N-H), 11.28(s, 2H, benzimidazole N-H). 13C NMR (DMSO-d6,100 MHz, ppm) 115.17, 122.61, 127.46, 128.92,129.01, 130.88, 134.51, 138.06, 152.78, 166.49,166.79, 167.42. MS (ESI) m/z: 425.1874 [M+H]+calcd. for C24H2oN602: 424.1648.

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 5805-57-2.

Reference:
Article; Jain, Anshu; Gupta, Ragini; Agarwal, Madhu; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 56A; 5; (2017); p. 513 – 518;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4331-29-7, name is 1H-Benzo[d]imidazol-7-amine, 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: 4331-29-7

-(Benzyloxy)-2-methyl-4H-pyran-4-one (450 mg, 2.081 mmol) and lH-benzimidazol-4-amine (279 mg, 2.095 mmol) were taken up in 40percent HOAc/3/40 (10 ml) in a microwave vial. The vial was sealed and the mixture heated to 140 ¡ãC for 30 min by microwave irradiation. The reaction was incomplete by LC MS. The mixture was heated to 200 ¡ãC for 30 min by microwave irradiation. The reaction was incomplete by LC/MS, The mixture was heated to 170 ¡ãC for 1 h by microwave irradiation. The mixture was concentrated. The crude material was purified by preparative reversed-phase HPLC (30x150mm Waters Sunfire (0.1percent TFA), 5- 35percent ACN/water over 20 min at 50 mL/min, 2 injections). Fractions containing each compound were pooled separately then applied to separate Phenomenex Strata-X-C ion exchange columns (5g). Each column was washed with 3/40 and MeOH (discard) then with 10percent concentrated NH4OH in MeOH (collect). The collected fractions for each were concentrated separately to give the title compounds below: l-(lH-benzimidazoi-4-yl)-5-(benzyloxy)-2-methylpyridin-4(lH)-one: tan solid LC/MS rt=1.24 min, 1H NMR (500 MHz, d6-DMSO) 5 12.90 (bs, 1 H), 8.33 (s, 1 H), 7.72 (bs, 1 H), 7.49 (bs, 1 H), 7.41-7.25 (m, 7 H), 6.26 (s, 1 H), 4.94 (s, 2 H), 1.92 (s5 3 H).l-(lH-benzimidazol-4-yl)-5-hydroxy-2-methylpyridin-4(l /)-one: tan solid, LC/MS rt = 0.47 min, 1H MR (500 MHz, d6-DMSO) delta 12.88 (bs, 1 H), 8.32 (s, 1 H), 7.70 (d, J = 8.06 Hz, 1 H), 7.38-7.25 (m, 3 H), 6.25 (s, 1 H), 1.92 (s, 3 H). l-[l-(2-Chloro-6-fluorobenzyl)-lH-benzimidazol-4-yl]-5-hydroxy-2-methylpyridin-4(l//)-one

The synthetic route of 4331-29-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOLKENBERG, Scott; BARROW, James, C.; POSLUSNEY, Michael, S.; HARRISON, Scott, T.; TROTTER, B. Wesley; MULHEARN, James; NANDA, Kausik, K.; MANLEY, Peter, J.; ZHAO, Zhijian; SCHUBERT, Jeffrey, W.; KETT, Nathan; ZARTMAN, Amy; WO2011/109254; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

General procedure: LHMDS (1.65 mL, 1 M in THF, 1.65 mmol, 5.0 equiv) was added dropwise to a solution of ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate (67.6 mg, 0.33 mmol, 1.0 equiv) and 1-(4-methoxybenzy-l)-1H-thieno[2,3-d][1,3]oxazine-2,4-dione (0.33 mmol, 1.0 equiv) in anhydrous THF (15 mL) at -78 C. The resulting solution was slowly warmed to room temperature and then stirred overnight at 80 C. After the reaction completed, quenched with a small amount of NH4Cl (aq, satd). And then concentrated in vacuo, the resulting crude material was purified by column chromatography (petroleum ether/ethyl acetate/acetic acid = 500:100:20, v/v/v) on silica gel to afford the product as a white solid.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Pinrao; Peng, Peng; Han, Mengmeng; Cao, Xianchao; Ma, Xiaodong; Liu, Tao; Zhou, Yubo; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4882 – 4892;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem