Category: imidazoles-derivatives

Application of 21252-69-7,Some common heterocyclic compound, 21252-69-7, name is 1-Octyl-1H-imidazole, molecular formula is C11H20N2, 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 solution of 1,3-dibromo-2-propyl glycoside 2 (1 mmol) and thealkylated imidazole 3 (6 mmol) in xylene (2 mL) was heated to 125 ¡ãC for 2 h. The solvent was evaporated before the crude product wastaken up in MeCN (10 mL) and extracted 4 times with hexane (60 mL) to remove remaining imidazole 3. The acetonitrile phase was concentrated under reduced pressure to provide the desired product 4 as pale yellow syrup in yields higher than 90percent.

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

Reference:
Article; Salman, Abbas Abdulameer; Goh, Ean Wai; Heidelberg, Thorsten; Hussen, Rusnah Syahila Duali; Ali, Hapipah Mohd; Journal of Molecular Liquids; vol. 222; (2016); p. 609 – 613;,
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. 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C14H19N3O2

[0079] To a solution of 81.3 g (650.6 mmol) 2-bromoethanol, 1 g potassium iodide and 100 g water was added 17.0g (65 mmol) compound (6). The reaction mixture was heated to 65-70 C and held at this temperature for 8 h to 12 h.The pH value of the solution was held between 4.2-5.5 during this period by dropwise addition of a solution of 20.0 g(151.4 mmol) diammonium hydrogen phosphate in 35 g water. The control of pH over the duration of the reaction waseffected through use of a pH electrode. The conversion was followed by HPLC. The reaction was continued until thefraction of compound (7A) was ? 1.5 %. Thereby ca. 8% of compound (7B) had formed and the proportion of compound(7) was ca. 87%. The reaction mixture was subsequently concentrated to dryness at ca. 55-60 C under vacuum. Tothe residue was added 150 g water and, preferably with an alkali metal carbonate, the pH value adjusted to ca. 8.5. Thedesired product (7) was extracted with 200 g methylene chloride or 225 g chloroform, and the organic phase subsequentlywashed with 60 – 80 g water. The organic phase was then concentrated to dryness and the remaining oil or alreadycrystalline residue dissolved in 200 g ethyl acetate or alternatively in 60 g actetonitrile. Compound (7) crystallised at ca.5 C and was filtered under suction, washed with 20 g cold ethyl acetate or alternatively with 15 g cold acetonitrile anddried at 60 -70 C. The yield of compound (7) was 18.3 g (52.4 mmol) with a content of ? 98.2% (80.5 % of theory). Thecrude product contained ?0.6% compound (7A) and compound (7B) respectively as well as <0.15% of compound (7C).0082] Analogous to Example 4 but with use of 9.0 g (65 mmol) potassium carbonate dissolved in 12 g water to holdthe pH value between 4.2 - 5.5. Identical results in terms of yield and quality.[0084] This example is a scaled-up analogue of Example 6 with use of 340 g (1.3 mol) compound (6), 2000 ml waterand 1625 g (13 mol) 2-bromoethanol. The reaction was performed without potassium iodide at 69 - 70C.. The pH valuewas held between 4.2 - 5.5 using a solution of 138 g sodium carbonate (1.3 mol) in 500 g water. Until a content ofcompound (7A) of ?1.5% was reached, the duration of the reaction was 13.5 h. The yield of compound (7) was 365 gcrude and 343.5 g after recrystallisation from acetonitrile (75.6% of theory). According to the analysis of related databases, 3543-73-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); A1;,
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Imidazole | C3H4N2 – PubChem

Reference of 872-82-2, 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. 872-82-2, name is 2-(1H-Imidazol-5-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 108 2-{[2-(1H-Imidazol-4-yl)ethyl]thio}pyridine 0.5 g (4.4 mmol) of 4-(2-hydroxyethyl)-1H-imidazole and 0.49 g (44.4 mmol) of 2-mercaptopyridine are brought to reflux in 5 ml of 47% aqueous HBr for 24 h. The solvent is removed azeotropically with isopropanol under reduced pressure to provide the title compound in the form of a dihydrobromide monohydrate salt which, after crystallization from isopropanol, melts at 189-190 C.

The chemical industry reduces the impact on the environment during synthesis 2-(1H-Imidazol-5-yl)ethanol. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Institut National de la Sante et de la Recherche Medicale; Societe Civile Bioprojet; US5559113; (1996); A;,
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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. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(3-Chloropropyl)-1H-imidazole

Sodium hydride (15 mg, 0.37 mmol) was added to a solution ofcompound 31 (90 mg, 0.31 mmol) in dry 10 mL DMF at 0 C, after 0.5 h,1-(3-chloropropyl)-1H-imidazole (66 mg, 0.47 mmol) was added. Theresultant solution was heated at 65 C for 10 h. After cooling, the solutionwas poured into H2O (50 mL) and then extracted with EtOAc.The organic extracts were washed with brine and dried over Na2SO4.After removal of the solvent, the remaining solid was chromatographedon a silica gel column using CH2Cl2/MeOH (15:1) as eluent to afford asa yellow solid (0.97 g, 78%), mp: 164-166 C. 1H NMR (500 MHz,DMSO-d6) delta 8.76 (s, 1H), 8.59 (s, 1H), 8.38 (s, 1H), 8.16 (d, J=5.2 Hz,1H), 7.65 (s, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.48 (s, 1H), 7.26 (d,J=8.2 Hz, 1H), 7.03 (d, J=5.3 Hz, 1H), 6.86 (s, 2H), 5.43 (s, 1H),4.30 (t, J=6.5 Hz, 2H), 4.22 (t, J=6.5 Hz, 2H), 2.42 (m, 2H), 1.51 (s,6H). HRMS m/z (ESI+): Calculated for C23H24N6OH+ ([M+H]+):401.2090. Found 401.2093

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:
Article; Ye, Qing; Li, Qiu; Gao, Anhui; Ying, Huazhou; Cheng, Gang; Chen, Jing; Che, Jinxin; Li, Jia; Dong, Xiaowu; Zhou, Yubo; Chemical Physics Letters; vol. 718; (2019); p. 38 – 45;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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 mixture of 5-bromo-1-methyl-1H-imidazole (569 mg, 3.417 mmol) in THF (14 mL) at 0 C. was added iPrMgCl-LiCl (1.3 M in THF, 2.48 mL, 3.22 mmol) to provide a white suspension. This mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the mixture stirred at room temperature for 10 minutes. The reaction was then cooled to 0 C. in an ice-water bath and stirred at 0 C. for an additional 10 minutes. Then, a solution of 4-(3-(benzyloxy)-4-chloro-2-methoxyquinoline-6-carbonyl)benzonitrile (335 mg, 0.78 mmol, Intermediate 83: step a) in THF (8 mL) was added. The flask was rinsed with THF (1.5 mL), which was also added to the reaction. The resulting mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the reaction was allowed to stir at room temperature for 4 hours. The reaction was quenched by the addition of water (15 mL). The aqueous was then extracted with EtOAc (3*20 mL). The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness. The residue was triturated with Et2O, filtered and dried under air to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.01-7.99 (m, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.68-7.65 (m, 2H), 7.56-7.53 (m, 3H), 7.53-7.52 (m, 1H), 7.50-7.46 (m, 2H), 7.41-7.34 (m, 3H), 6.45-6.44 (m, 1H), 5.16 (s, 2H), 4.15 (s, 3H), 3.39 (s, 3H). MS (ESI): mass calcd. for C29H23ClN4O3, 510.2. m/z found, 511.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 51605-32-4, 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. 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of ethyl 4-methyl-1H-imidazole-5-carboxylate (7.30 g, 45.9 mmol) in THF (60 mL) is added MeOH (2.23 mL, 55.1 mmol) and triphenylphosphine (14.8 g, 55.1 mmol). The reaction is cooled to 0¡ã C. under N2 and diethyl azodicarboxylate (9.0 mL, 17.6 mmol) is added dropwise. The mixture is warmed to room temperature and stirred overnight. The volatiles are evaporated in vacuo. Ether (50 mL) is added. The mixture is stirred at room temperature for 30 minutes, filtered, the filter cake is washed with ether (50 mL). The filtrate and ether washings are combined and are sequentially washed with water (30 mL) and brine (30 mL). The organic phase is dried over Na2SO4, evaporated in vacuo to provide the crude product. The crude product is subjected to silica gel flash column eluting with 30percent EtOAc in hexanes to EtOAc to give the title compound (5.13 g, 59.8percent) as a yellow oil. LC/MS (m/z): 169 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-methyl-1H-imidazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; Hu, Zhi Long; Liu, Lian Zhu; Ma, Tianwei; Zhang, Haizhen; Zhou, Jingye; (25 pag.)US2018/194755; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4856-97-7, These common heterocyclic compound, 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, 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.

The resulting solid (1H-benzimidazol-2-yl) methanol (34 mmol) was dissolved in 250 mL of dichloromethane and stirredFollowed by addition of manganese dioxide (0.68 mmol). The temperature was raised to 40 C and stirring was continued for 2 hours to monitor the reaction. After the reaction is complete, the product is evaporated to drynessDichloromethane, 150 mL of tetrahydrofuran was added. Directly to the next step

Statistics shows that (1H-Benzoimidazol-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 4856-97-7.

Reference:
Patent; Shenyang Pharmaceutical University; Zhao Linxiang; Liu Dan; Li Kun; Ma Tianyi; Jing Yongkui; (13 pag.)CN107118249; (2017); A;,
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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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., name: 2-Phenyl-1H-imidazole-4-carbaldehyde

COMPOUND 12. 1.34 : 1- (DIETHYLAMINO) CARBONYUPHENYL-2-rC2- PHENYL-1-IMIDAZOL-5-YL) METHYL]-L24- TETRAHYDROISOQUINOLIN-6-YL METHANESULFONATE; INTERMEDIATE 6.4. 1 (27 mg, 0.067 mmol) and 2-phenyl-4 (5)- imidazolecarbaldehyde (23 mg, 0.134 mmol) were dissolved in 1,2-dichloroethane (3.0 mL) and sodium triacetoxyboronhydride (43 mg, 0.20 mmol) was added. The mixture was stirred for 18 h after which ethyl acetate and 1 M sodium hydroxide solution were added. After phase separation the aqueous phase was extracted with more ethyl acetate and the combined organic phases were washed with water and brine. Tosylhydrazine resin (100 mg, 1.5 mmol/g) was added and the mixture was stirred for 2 h. After filtration and thorough washing of the resin the filtrate was evaporated and the residue was purified by flash chromatography the product (36 mg (0.064 mmol, 96%). 1H NMR (500 MHz, CDC13) : 1.13, 1.27 (2 brs, 6H), 2.64, 2. 82, 3.10, 3.12 (4 m, 4H), 3.11 (s, 3H), 3.28, 3.56 (2 brs, 4H), 3.45, 3.56 (2 d, J 12. 0 Hz, 2H), 4. 68 (s, 1H), 6.68 (d, 8.5 Hz, 1H), 6.86 (s, 1H), 6.90 (dd, J 8.5, 2.0 Hz, 1H), 7.05 (d, J 2.0 Hz, 1H), 7.34 (m, 7H), 7.89 (d, J 7.5 Hz, 2H). (+) LRESIMS m/z 559 (100) [M+H] +.

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; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
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 29043-48-9 as follows. SDS of cas: 29043-48-9

To a stirred solution of 2-methyl-1 H-benzo[d]imidazol-5-amine (187 mg) in DCM (5 mL) at 0 C was added 3-carbamoyl-4-hydroxybenzene-1 -sulfonyl chloride (lnt-1 , 300 mg). The reaction mixture was allowed to warm to RT and stirred for 16 hr. The reaction mixture was diluted with water (30 mL) and extracted with DCM (2 x 50 mL). The combined DCM extracts were washed with saturated brine (25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product (300 mg). The crude product was purified by reversed phase preparative HPLC (Sunfire C18, 30 x 250 mm) using a gradient of 10-100% acetonitrile in 10 mM ammonium bicarbonate (aq). The desired fraction was concentrated under reduced pressure and the resulting solid was collected by filtration, washed with water (10 mL) and dried under vacuum to afford the titled compound (55.6. mg). LCMS m/z 347.04 (M+H)+. NMR after D20 exchange (400 MHz, DMSO-c/6) delta ppm 2.27 – 2.50 (m, 3 H) 6.76 (d, J=8.33 Hz, 1 H) 6.85 (dd, J=8.55, 1 .75 Hz, 1 H) 7.02 – 7.21 (m, 1 H) 7.28 (d, J=8.33 Hz, 1 H) 7.40 – 7.61 (m, 1 H) 8.19 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 29043-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem