Category: imidazoles-derivatives

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. 7152-24-1, name is 2-(Methylthio)benzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 7152-24-1

General procedure: A mixture of KOH and 2-methylmercaptobenzimidazole was stirred in DMF at room temperature for 1 h. The dibromo compound was added to the above reaction mixture was allowed to stir continuously at room temperature for 24 h. The reaction was quenched by adding water. The resulting powder was collected by filtration and was dried.

The synthetic route of 7152-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rajakannu, Palanisamy; Elumalai, Palani; Mobin, Shaikh M.; Lu, Kuang-Lieh; Sathiyendiran, Malaichamy; Journal of Organometallic Chemistry; vol. 743; (2013); p. 17 – 23;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-59-7, 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 16681-59-7 as follows.

2-Bromo-l -methyl- 1H- imidazole (47 mu-, 0.48 mmol) was dissolved in diethyl ether (2 mL) and cooled to -75C under argon. Butyl lithium (2.5 M in hexanes: 192 (uL, 0.48 mmol) was added dropwise and the mixture stirred at -75C for 1 hour. A solution of (R)-l-(4- fluorophenyl)-6-((4-(trifluoromemyl)phenyl)sulfonyl)-4,4a,5,6,7,8-hexahydro-lH-pyra.zolo[3,4- g]isoqumoline~4a~carbaldehyde (252 mg, 0.5 mmol) in diethyl ether (2 mL) was added dropwise The reaction mixture was stirred for 16 hours whilst warming slowly to room temperature. The reaction mixture was cooled and treated with water (10 mL) and the phases separated. The organic phase was extracted with further diethyl ether (x2) followed by diehloromethane (x2). The combined organic phases were dried over sodium sulfate, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient: 17.5 to 25% acetone in cyelohexane) to afford (R)-(l-(4-fluorophenyl)-6-((4-(Mflu^ pyrazolo[3,4-g]isQquinoim-4a-yi)(l as a white powder (82 mg) LCMS (Method A, ESI): RT 2.74 min, m+H = 588.1

According to the analysis of related databases, 16681-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORCEPT THERAPEUTICS, INC.; HUNT, Hazel; JOHNSON, Tony; RAY, Nicholas; WALTERS, Iain; WO2013/177559; (2013); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, molecular formula is C5H5N3, 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. Computed Properties of C5H5N3

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98873-55-3, its application will become more common.

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2301-25-9, name is 1-(4-Nitrophenyl)-1H-imidazole, 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 2301-25-9, name: 1-(4-Nitrophenyl)-1H-imidazole

Part B. Preparation of 1-(3-cyanophenyl)-3-methyl-5-[(4′-(N-imidazolyl)phenyl)aminocarbonyl]pyrazole The product from part A was then coupled to 1-(3-cyanophenyl)-3-methylpyrazole-5-carboxylic acid via the acid chloride methodology described previously to afford the desired amide which was then purified via standard reverse phase HPLC techniques to afford the desired material. 1 H-NMR (DMSO-d6, 300 MHz) delta: 10.73 (s,1H) 9.35 (bs,1H) 8.13 (s,1H) 7.95 (s,1H) 7.90-7.60 (complex,8H) 7.0 (s,1H) 2.30 (s,3H) ppm; ESI mass spectrum analysis m/z (rel. intensity) 369 (m+H, 100); HRMS calc. mass 369.146384; found 369.145884.

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; DuPont Pharmaceuticals Company; US6020357; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 570-22-9, 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. 570-22-9 name is 1H-Imidazole-4,5-dicarboxylic acid, 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.

A mixture of CuCl2 (0.2 mmol, 26.9 mg), 4,5-H3imdc(0.1 mmol, 15.8 mg), and phen (0.1 mmol, 19.8 mg) in themolar ratio of 2:1:1 was dissolved in 4 mL distilled water and4 mL DMF (DMFDN,N0-dimethylformamide) and stirred30 min. Then, the mixture was transferred and sealed in10 mL glassflask heated at 85C for 96 h. After the samplewas cooled to room temperature, the crystals were washedwith distilled water and blue strip crystals werefiltered offand dried at room temperature. The yield of the blue crystalline product was 54% (based on Cu). Anal. Calcd forC17H10N4O4Cu: C, 51.28; H, 2.51; N, 14.08%. Found: C,51.13; H, 2.49; N, 14.02%. IR (KBr, cm1): 3687(w), 3045(m), 1683(m), 1572(s), 1474(s), 1428(s), 1238(m), 1107(m),995(w), 851(m), 779(w), 720(m), 675(w), 511(w).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Huijie; Zhou, Guangpeng; Fan, Ruiqing; Wang, Xinming; Yang, Yulin; Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry; vol. 46; 8; (2016); p. 1224 – 1235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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. Computed Properties of C4H3N3

lH-imidazole-4-carbonitrile (1 g, 10.74 mmol) and potassium carbonate (2.97 g, 21.49 mmol) were added to a round bottomed flask and placed under an atmosphere of nitrogen by evacuation-refill. Acetone (10 mL) was added, evacuation-refill of the vessel repeated, and the mixture stirred prior to addition of (2- (chloromethoxy)ethyl)trimethylsilane (2.091 mL, 11.82 mmol). The reaction vessel was placed under an atmosphere of nitrogen and stirred at RT for 48 h. The solvent was removed under reduced pressure, and the residue redissolved in 30 mL EtOAc and washed sequentially with 20 mL water and 20 mL brine. The combined aqueous layers were extracted with further EtOAc (2 x 30 mL). The organic layers were combined and passed through a hydrophobic frit, and the solvent was removed under reduced pressure. The sample was dissolved in DCM and purified by column chromatography using a silica cartridge (120 g) with an ethyl acetate-cyclohexane solvent system [3CV, 10-20percent; 3CV, 20percent; 5CV, 20-50percent; 9CV, 50percent]. The appropriate fractions were combined and the solvent removed in vacuo to afford the title compound in a 2: 1 ratio of the l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole-4-carbonitrile and l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-5-carbonitrile regioisomers, as a pale yellow oil (1.71 g, 7.66 mmol, 71percent). LCMS (System B): tRET = 1.08 min; MH+ 224 (both regioisomers). l-((2-(Trimethylsilyl)ethoxy)methyl)-lH-imidazole-4-carbonitrile (for an example preparation, see Intermediate 15, 1.68 g, 7.52 mmol (2: 1 ratio of l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-4-carbonitrile and H(2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-5-carbonitrile)) was added to a round bottomed flask containing THF (40 mL). Once dissolved, /V-bromosuccinimide (1.473 g, 8.27 mmol) was added, and the flask placed under an atmosphere of nitrogen. The reaction mixture was stirred at 60 °C overnight. Further 0.2 equivalents of /V-bromosuccinimide (0.268 g, 1.504 mmol) was added to the reaction mixture and the reaction left stirring at 60 °C for a further 8h. The reaction mixture was quenched with saturated sodium hydrogencarbonate solution (40 mL) and brine (40 mL) and extracted with EtOAc (3 x 40 mL). The combined organic layers were passed through a hydrophobic frit and the solvent removed under reduced pressure. The sample was loaded as a neat liquid and purified by column chromatography using a silica cartridge (80 g) with an ethyl acetate-cyclohexane solvent system [3CV, 0percent; 7CV, 0-10percent; 3CV, 10percent]. The appropriate fractions were combined and the solvent removed in vacuo to give the crude product. The crude product was dissolved in diethyl ether and filtered through Celite®, the solvent was removed from the filtrate under reduced pressure to afford the title compound as a pale yellow oil, (1.24 g, 4.10 mmol, 55percent). LCMS (System A): tRET = 1.23 min; MH+ 302, 304.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAXTER, Andrew; BIT, Rino, Antonio; BROWN, John, Alexander; HIRST, David; HUMPHREYS, Philip; JONES, Katherine, Louise; PATEL, Vipulkumar, Kantibhai; (124 pag.)WO2018/41964; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 52099-72-6, A common heterocyclic compound, 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C10H10N2O, 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.

EXAMPLE IX To a stirred solution of 8.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one in 45 parts of N,N-dimethylformamide are added portionwise 1.7 parts of a sodium hydride dispersion 78%. After stirring for 1 hour at room temperature, the whole is cooled to 0-5 C and 8.65 parts of 1-bromo-3-chloropropane are added dropwise (slowly). Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured into crushed ice and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 5.5 parts (44%) of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)2H-benzimidazol-2-one; mp. 115 C.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4066772; (1978); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17289-19-9, These common heterocyclic compound, 17289-19-9, name is Methyl 1-methyl-1H-imidazole-4-carboxylate, 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.

To a solution of Example 63a (1.40 g, 10.0 mmol) in CHC13 (30.0 mL) was added NBS (2.13g, 12.0 mmol). The reaction mixture was then stirred 18hrs at 50C and then cooled to room temperature. The residue was extracted with EtOAc (200 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product Example 63b (500 mg, yield 22.8%). NMR (400 MHz, Chloroform- ) delta 7.60 (s, 1H), 3.91 (s, 3H), 3.67 (s, 3H).

The synthetic route of 17289-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); 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. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Formula: C5H6N2O2

General procedure: Method B: Compounds 22 or 23 (1.2 mmol) and cesium carbonate (390 mg, 1.2 mmol) were dissolved in dry DMF (3 mL) under argon. After stirring of the mixture for 30 min at 50 C, a solution of the tosyl ester 12c or 12d (1 mmol) dissolved in dry DMF (3 mL) was added and the stirring was continued overnight at 50 C under argon. After evaporation of DMF in high vacuo, the residue was dissolved in EtOAc and the organic phase was washed with brine to neutral pH, dried over Na2SO4 and evaporated under reduced pressure. The residual product was purified by column chromatography (silica gel) using the appropriate solvent systems as it will be defined, in each case, below.

The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moutevelis-Minakakis, Panagiota; Papavassilopoulou, Eleni; Michas, George; Georgikopoulou, Kalliopi; Ragoussi, Maria-Eleni; Neophytou, Niki; Zoumpoulakis, Panagiotis; Mavromoustakos, Thomas; Hadjipavlou-Litina, Dimitra; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2888 – 2902;,
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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example 4 3-(1H-benzimidazol-2-methylene)-5-(cyclohexylaminosulfo)-2-indolone (Indo 4) 0.15 g (0.5 mmol) 5-(cyclohexylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.17 g pale yellow solid, with a yield of 80.6percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.86 (s, 1H), 11.68 (s, 1H), 8.35 (s, 1H), 8.08 (s, 1H), 7.76-7.84 (m, 3H), 7.48 (d, 1H, J=7.2 Hz), 7.66 (d, 1H, J=6.4 Hz), 7.38 (t, 1H), 7.31 (t, 1H), 7.10 (d, 1H, J=8.0 Hz), 3.02 (b, 1H), 1.60 (b, 5H), 1.50 (b, 5H). ESI-MS m/z: 421 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(cyclohexylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is cyclohexylaminosulfo, and R2 is hydrogen.

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem