Imidazoles-derivatives

144689-93-0, 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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below.

Toluene (180 L) is placed into a reactor and water (3.17 L) is added, followed by addition of ethyl-4-(1 -hydroxy-1 -methylethyl)-2-propylimidazole-5- carboxylate (18.0 Kg). The mass is stirred for about 10 minutes, heated to about 45C, and potassium carbonate (25.85 Kg) is added. The temperature of the mass is raised to about 65C and maintained for about 45 minutes. N-(triphenylmethyl)- 5-[4′-(bromomethyl)biphenyl-2-yl]tetrazole (48.9 Kg) and tetrabutylammonium bromide (4.82 Kg) are added at the same temperature and the mixture is stirred at 60-700C for 10 hours. Reaction completion is verified using thin layerchromatography (TLC). After the reaction is complete, the mass is washed with water (3*120 L) at about 500C. The mass is cooled to about 25C and toluene (468 L) and potassium tertiary-butoxide (12.6 Kg) is added, then the mass is maintained at the same temperature for about 1 hour. Water (0.85 L) is added and the mass is maintained at the same temperature for about 2 hours. Reaction completion is verified using TLC, then 5-methyl-2-oxo-(1 ,3-dioxolene-4-yl)methyl chloride (20 Kg), tetrabutylammonium bromide (4.82 Kg), and sodium carbonate (3.96 Kg) are added at 40-450C. The mass is stirred at about 55C for about 11 hours. After the reaction is complete, the mass is cooled to about 20C, water (540 L) is added and the pH is adjusted to about 6-7 by adding 10% aqueous HCI. The layers are separated. The aqueous layer is extracted with toluene (240 L). The organic layers are combined and washed with water (270 L). The solvent is distilled under reduced pressure. Acetone (189 L) is added to the residue and the mixture is heated to about 45C to produce a solution, then the solution is cooled to about 300C and maintained for about 20 minutes, followed by cooling to about 2C and maintaining for about 3 hours. The formed solid is filtered, washed with acetone (54 L), and dried for about 4 hours. The material obtained is re- crystallized from acetonitrile to yield 34.0 Kg of the title compound.

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; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; MANNE, Nagaraju; NAREDLA, Anitha; SHINDE, Sachin Gulabrao; WO2011/14611; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below.

l-Beiuothiazol-6->l-imidazolidm-2-one lL-_84b: 15Umg, 0.6849mmol) was reacted with 5>br¡ãnkappa>-. -methyl- U l-imidazole (12l.3mg, O.753mmol).1.4’diox?nie (SmL). copper iodide ( 12.99mg, 0.0684mmol). trans N.N’-diim’th^l-cyclohexane- 1 ,2-diamine (2l>.176mg.0.20Smiotanol) and potassium phosphate (435.0 ling, 2.05mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOl ) in CIlCI.? ) afforded 85mg of the product (4l.o4% >ield).1I I NMR (300 MH/. CDCh): o 8.9 (?, HIV 8.35 (d.1 M).8. l(d. III).7.7 (dd. III). 7.5-7.4(brs, IH),7.0(brs, HH.4.1 (t, 211), 3.9 (t.211), 3.6 (s.311).I CMS: 100%,inV 299.8 (M+ 1)HPLC: 98.52%

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; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2010/149755; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 98873-55-3

A 10 mL schienk tube was charged with powdered KOH (116 mg, 2.07 mmol), DMSO (1 mL), purged with Argon and cooled at 18CC with a water bath. A solution of 2-imidazol-1- ylacetonitrile (104 mg, 0.97 mmol) and CS2 (117 pL, 1.9408 mmol) in DMSO (500 pL) is then added slowly to give an orange mixture. The cooling bath is removed and the reaction is stirred at room temperature for 30 minutes. Then a solution of freshly prepared (2-bromo-5-fluoro-indan-1-yl)methanesulfonate (step 3) in DMSO is added dropwise. After 30 minutes stirring at room temperature, the reaction is poured into H20 (20 mL). The aqueous phase is extracted with AcOEt (3 x 5 mL), the combined organic phases were washed with H20 (10 mL), brine (10 mL), dried with Mg504, filtered and evaporated to give a crude pale yellow residue. Purification by chromatography on silica gel (heptanes/ethylacetate 2:1-1:3) afford2-(6-fluoro-4,8b-dihydro-3aH-indeno[1 ,2-d][1 ,3]dithiol-2-ylidene)-2-imidazol-1 -yl-acetonitrile as an inseparable (2:1) mixture of E/Z-isomers.

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, 98873-55-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel; BONVALOT, Damien; JEANMART, Stephane, Andre, Marie; WO2015/11194; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9, The chemical industry reduces the impact on the environment during synthesis 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, I believe this compound will play a more active role in future production and life.

A mixture of CaCl2 (0.012 g, 0.1 mmol), H3imdc (0.039 g,0.25 mmol), Zn(Ac)2?2H2O (0.022 g, 0.1 mmol) and a buffer solution of HAc-NaAc (pH = 5.7, 2 mL) was put into 25 mL Teflon-lined stainless steel autoclave and heated at 180 C for 3 days, then cooled to room temperature. Dark yellow block crystals were obtained by filtration to give a yield of 32.7% (0.010 g). Elemental Anal. Calc. for C12H8Ca2N4O12Zn2: C, 23.58; H, 1.32; N, 9.17. Found: C, 23.22; H, 1.37; N, 8.95%. IR (KBr, cm-1): 3448 s, 1600 s, 1482 vs 1400 s, 1252 m, 1105 m, 804 m, 664 m.

The chemical industry reduces the impact on the environment during synthesis 1H-Imidazole-4,5-dicarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ablet, Ayjamal; Li, Shu-Mu; Cao, Wei; Zheng, Xiang-Jun; Jin, Lin-Pei; Polyhedron; vol. 83; (2014); p. 122 – 129;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life. 16042-25-4

5 (1.00 g, 3.30 mmol) and 1H-imidazole-2-carboxylic acid(0.40 g, 3.60 mmol) were dissolved in 3 mL sulfolane, and 12 mLPOCl3 was added. The reaction mixturewas stirred at 85 C for 18 h,then cooled to room temperature, poured into 200 mL ice water.NaOH was added to adjust the PH to 7. The mixturewas filtered anddried in vacuo to give 92 mg of 11-3 as gray solid: 7% yield. 1H NMR(300 MHz, DMSO-d6) delta 13.83 (s, 1H), 8.77 (d, J = 5.4 Hz, 1H), 8.01 (d,J = 9.0 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J = 2.5 Hz, 1H), 7.28 (d, J =5.2 Hz,2H), 7.18 (dd, J= 9.2, 2.6 Hz, 1H), 5.82 (s, 2H), 3.90 (s, 3H); m.p.:205-207 C; HRMS (ESI+) m/z 380.0914 (380.0924 calcd forC17H14N7O2S+, [M+H]+).

The chemical industry reduces the impact on the environment during synthesis 16042-25-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Haoliang; Liu, Qiufeng; Zhang, Li; Hu, Shihe; Chen, Tiantian; Li, Huifang; Chen, Yadong; Xu, Yechun; Lu, Tao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 491 – 502;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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 synthesis method is as follows: In a 100 ml single-mouth flask, add 2.85g (10mmol) dehydroabietylamine, 1.87g (12mmol) imidazol-4,5-dicarboxylic acid (molar ratio of 1:1.2) and 50 ml of toluene. 110 C reflux condenser reaction 8h. After the reaction heat filter, steaming and obtaining white solid, quality is 2.0329g, yield of 46.1%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole-4,5-dicarboxylic acid, its application will become more common.

Reference:
Patent; Nanjing Forestry University; Xu, Li; Zhao, Fengyi; Xu, Yuanyuan; Yang, Shilong; Sun, Li; Wang, Luna; Wang, Weifan; (9 pag.)CN105037191; (2017); B;,
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 96797-15-8 as follows. 96797-15-8

A. 5- (LH-IMIDAZOL-4-YL)-2-CHLORO-PYRIDINE. To a solution OF 4-IODO-1- TRITYL-LH-IMIDAZOLE (72.8 g, 166 mmoles) in THF (400 ml) at room temperature was added ethylmagnesium bromide (200 ml, 200 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (27.2 g, 200 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (triphenylphosphine) palladium (20 g, 16.6 mmoles) and 5-bromo-2-chloropyridine (38. 48 g, 200 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane (1 L) and washed with a 30% NaOH solution containing an added 40 g of EDTA (3x 400 ml), with NACI (sat. ) (300 ml), dried over MGS04, filtered, and concentrated. To the crude material was added dichloromethane (600 ml) and trifluoroactetic acid (180 ml). After standing for 1 hour, the reaction was concentrated and pumped on overnight. To the resulting oily tar was added 1M HCl (100 ml) and the mixture was sonicated for 30 minutes and than filtered. The aqueous filtrate was washed with diethyl ether (400 ml). The ether layer was back extracted with 1 M HCL (2x 20 ml). The combined aqueous layers were washed with diethyl ether (2x 200 ml). The aqueous layer was cooled in an ice bath and the pH was adjusted by addition of a 30% NaOH solution until the pH was around 9-10. The resulting solid was filtered, rinsed with cold water (20 ml), rinsed with diethyl ether (20 ml), and pumped on yielding 5- (LH-IMIDAZOL-4-YL)-2-CHLORO-PYRIDINE (12.90 g, 43%). MH+ (180)

According to the analysis of related databases, 96797-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3543-73-5, 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.

To a solution of 81.3 g (650.6 mmol) 2-bromoethanol, 1 g potassium iodide and 100 g water was added 17.0 g (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 was effected through use of a pH electrode. The conversion was followed by HPLC. The reaction was continued until the fraction 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. To the residue was added 150 g water and, preferably with an alkali metal carbonate, the pH value adjusted to ca. 8.5. The desired product (7) was extracted with 200 g methylene chloride or 225 g chloroform, and the organic phase subsequently washed with 60-80 g water. The organic phase was then concentrated to dryness and the remaining oil or already crystalline residue dissolved in 200 g ethyl acetate or alternatively in 60 g acetonitrile. 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 and dried 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). The crude contained ?0.6% compound ( 7A) and compound (7B) respectively as well as <0.15% of compound (7C). The crude product obtained was recrystallized from ethyl acetate, or alternatively from acetonitrile, toluene, propan-2-ol, tetrahydrofuran, acetone, isopopyl acetate or water, prior to further conversion to compound ( 8). Thereby the yield of compound (7) was 17.2 g (94.0% recrystallization yield) with a content of >99.2%, wherein compound (7A) was removed below a content of 0.2% and compound (7B) below 0.3%. Through the course of the reaction, the content of compound (7C) was kept below 0.15%, as this compound can only poorly be removed by recrystallization from the above described solvents. The overall yield of this step was 76.5% of theory and was thus ca. 12.5% higher than that described in the procedure using ethylene oxide as according to DD34727 and ca. 31% higher in comparison to the favoured procedure of WO2011079193 involving addition of Huenig’s base.

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; Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG; Frey, Michael; Walther, Dirk-Detlef; US2014/31560; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, 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 96797-15-8. 96797-15-8

873 mg of 4-iodo-1-triphenylmethylimidazole, 750 mg of 2-ethoxycarbonylimidazo[1,2-a]pyridine-6-boronic acid, 23 mg of palladium acetate and 70 mg of (2-biphenyl)dicyclohexyl-phosphine are degassed under vacuum and then suspended, under argon, in a degassed mixture of 15 mL of toluene, 5 mL of water and 5 mL of N-methylpyrrolidone. After addition of 950 mg of potassium phosphate, the mixture is degassed under vacuum and then placed under argon and heated for 15 minutes at 100 C. by microwave, then cooled, diluted and stirred in a mixture of 50 mL of saturated sodium bicarbonate solution and 50 mL of dichloromethane. The organic phase is dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The residue is chromatographed on silica, eluding with a mixture of ethyl acetate and hexane. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure to give 508 mg of ethyl 6-(1-triphenylmethyl-1H-imidazol-4-yl)imidazo[1,2-a]pyridine-2-carboxylate. 1H NMR spectrum (DMSO-d6, delta in ppm): 8.97 (s, 1H), 8.54 (s, 1H), 7.76-7.72 (m, 1H), 7.56-7.52 (m, 3H), 7.47-7.37 (m, 9H), 7.20-7.17 (m, 6H), 4.31-4.27 (m, 2H), 1.34-1.20 (m, 3H). Mass spectrum (APCI): m/z=499 [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 4-Iodo-1-trityl-1H-imidazole.

Reference:
Patent; sanofi-aventis; US2010/317686; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, The chemical industry reduces the impact on the environment during synthesis 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a solution of 1 -methyl- lH-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane- 1 , 3 -diol (4.01 g, 52.7 mmol) and CSA (0.306g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H)

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

Reference:
Patent; METHYLGENE INC.; WO2009/109035; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem