Category: imidazoles-derivatives

1615-14-1, 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 1615-14-1 as follows.

EXAMPLE 50 7-[2-(1H-1-Imidazolyl)ethoxy]-4H-4-chromenone Under N2, a solution of 0.75 g (4.6 mmol) of 7-hydroxy-4H-4-chromenone (J. Med. Chem., 1991;34:248) in 20 mL of THF was treated with 1.21 g (4.6 mmol) of triphenylphosphine and 0.5 g (5.1 mmol) of 2-(1H-1-imidazolyl)-1-ethanol and the solution cooled in ice. This was then treated over 10 minutes with 0.72 mL (4.6 mmol) of diethyl azodicarboxylate, and the solution stirred at room temperature overnight. The solution was diluted with EtOAc, washed twice with H2 O, twice with saturated NaHCO3, and then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. Chromatography on silica gel, eluding with a gradient of CH2 Cl2 to CH2 Cl2 /MeOH (96/4) gave 0.12 g (10% yield) of the product as a pink solid, mp 131-133 C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 257 (M+H+). Calculated for C14 H12 N2 O3 *0.08 CH2 Cl2 (MW 262.76): C, 64.34; H, 4.66; N, 10.66. Found: C, 64.34; H, 4.72; N, 10.66.

According to the analysis of related databases, 2-(1H-Imidazol-1-yl)ethanol, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US6133303; (2000); A;,
Imidazole – Wikipedia,
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23785-21-9, The chemical industry reduces the impact on the environment during synthesis 23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a stirred solution of XLIV, (2 g; 14 mmol) in dimethylformide (50 ml) was added trityl chloride (3.98 g; 14 mmol) and triethylamine (1.73 g, 17 mmol) at 0C. The resulting solution was stirred for 12 h at room temperature. The reaction mixture was cooled, concentrated at reduced pressure and diluted with water. The aqueous layer was extracted with ethyl acetate.The combined organic layers were washed with brine, dried over Na2504, filtered and concentrated under vacuum to afford ethyl 1 -trityl- 1 H-imidazole-4-carboxylate as a brown solid (XLV; 3 g, 55% yield). MS (M+1) 383.34.

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

Reference:
Patent; NORGINE B.V.; BAKTHAVATCHALAM, Rajagopal; BASU, Manas Kumar; BEHERA, Ajit Kumar; VENKATESHAPPA, Chandregowda; HEWSON, Christopher Alexander; KADNUR, Sanjay Venkatachalapathi; KALINDJIAN, Sarkis Barret; KULKARNI, Bheemashankar; SAXENA, Rohit; SURESH, Juluri; VISWANATHAN, Vellarkad; ZAINUDDIN, Mohd; DHARSHINIS, Akila Parvathy; KRISTAM, Rajenda; WO2015/97122; (2015); A1;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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. 16042-25-4

To a suspension of 0.31 g of imidazole-2-carboxylic acid (2.76 mmol) in 14 ml DMF was added 0.448 g of CDI (2.76 mmol), 0.38 ml triethylamine (2.76 mmol) and stirred at ambient temperature for 1 h. Then the mixture was refluxed for 30 min. After cooling to ambient temperature, 0.5 g of 5-phenyl-o-anisidine (2.5 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was evaporated and the residue taken up in water (40 ml) and extracted 3 times with methylene chloride. The combined organic phases were tried on sodium carbonate, evaporated and the residue was stirred in hot ethyl acetate. After filtration and drying, 0.11 g 1H-imidazole-2-carboxylic acid (4-methoxy-biphenyl-3-yl)-amide (14%) were obtained as a light yellow solid; M.p.: 276 C. 0.1 g of 1H-Imidazole-2-carboxylic acid (4-methoxy-biphenyl-3-yl)-amide (0.36 mmol) was taken up in toluene (5.0 ml) and treated with 0.435 g of Lawesson reagent (1.0 mmol). The reaction mixture was heated to reflux for 16 h. After cooling to ambient temperature, water (25 ml) was added and the mixture was extracted 3 times with dichloro methane. The combined organic phases were dried on sodium carbonate, evaporated and the residue triturated in methanol. 0.08 g of 1H-imidazole-2-carbothioic acid (4-methoxy-biphenyl-3-yl)-amide (73%) were obtained as a yellow solid; M.p.: 223-226 C. [0204] 0.049 g of 1H-Imidazole-2-carbothioic acid (4-methoxy-biphenyl-3-yl)-amide (0.16 mmol) was taken up in chloroform and treated with 8.1 mul of Br2 (0.16 mmol) for 4 h at reflux. Then the reaction was quenched with sodium thiosulfate (38%) and extracted with chloroform. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography (silica gel, methylene chloride/methanol 40:1) to yield 0.016 g of 2-(1H-imidazol-2-yl)-4-methoxy-7-phenyl-benzothiazole (33%) as a colorless solid; M.p.: 205-206 C.

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 16042-25-4.

Reference:
Patent; Flohr, Alexander; Jakob-Roetne, Roland; Norcross, Roger David; Riemer, Claus; US2004/229862; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. 60-56-0

2-chlorosulfonyl-1-methylimidazole Bleach (12% w/w aq, 110 ml) was cautiously added dropwise to a solution of 2-mercapto-1-methylimidazole (2.0 g) in conc. H2SO4 (50 ml) cooled to 0 C. After stirring 30 minutes at 0 C. the mixture was diluted with H2O (30 ml) and dichloromethane (30 ml). The aqueous layer was re-extracted with dichloromethane and the combined organic layers dried (MgSO4) and evaporated to give the product as an oil (730 mg).

Statistics shows that 60-56-0 is playing an increasingly important role. we look forward to future research findings about 1-Methyl-1H-imidazole-2(3H)-thione.

Reference:
Patent; Lewis, Huw David; Harrison, Timothy; Shearman, Mark Steven; US2009/215775; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 934-22-5, name is 6-Aminobenzimidazole, I believe this compound will play a more active role in future production and life. 934-22-5

2,3-Dibromo-5-ethoxy-6-hydroxybenzaldehyde (0.1 g, 0.31 mmol), 5-Aminobenzimidazole (0.03 g, 0.20 mmol), and isoamyl alcohol (2 mL) were stirred at room temperature under N2. Acetic acid (0.07 mL) was added drop-wise, and the mixture was refluxed overnight. The reaction mixture was filtered, washed with CH2Cl2, MeOH, and dried to yield 29 (0.06 g, 0.13 mmol, 65.4%) as an orange powder. 1H NMR (DMSO, 300 MHz) delta 15.57 (s, 1H), 12.50 (bs, 1H), 9.20 (s, 1H), 8.31 (s, 1H), 7.81-7.68 (m, 2H), 7.38 (s, 1H), 7.35 (s, 1H), 4.10 (q, 2H, J=6.9 Hz), 1.36 (t, 3H, J=6.9 Hz); 13C NMR (DMSO, 700 MHz) delta 162.36, 154.82, 148.63, 144.23, 140.92, 120.40, 119.77, 117.69, 117.42, 117.30, 116.15, 113.00, 111.88, 104.91, 65.01, 15.00. Rf=0.48 (CH2Cl2/MeOH 9:1)

The chemical industry reduces the impact on the environment during synthesis 934-22-5. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shim, Hyun Jae; Yang, Hye Ran; Kim, Han Ie; Kang, Shin-Ae; No, Kyoung Tai; Jung, Young Hoon; Lee, Seung-Taek; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4659 – 4663;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2302-25-2, Adding a certain compound to certain chemical reactions, such as: 2302-25-2, name is 4-Bromo-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 2302-25-2.

The 2-(4-bromo-lH-imidazol-l-yl)-5-(trifluoromethyl)pyridine was obtained as follows:A dried pressure tube was charged with 4-bromo-lH-imidazole (100 mg, 667 muiotaetaomicron), tetrahydrofuran (3 ml), N,N-dimethylformamide (2 ml), 2-(methylsulfonyl)-5- (trifluoromethyl)pyridine (150 mg, 667 muiotaetaomicron), and cesium carbonate (261 mg, 800 muiotaetaomicron). The tube was sealed and heated at 105 C for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate = 100:0 to 60:30 as the eluent. The 2-(4-bromo-lH- imidazol-l-yl)-5-(trifluoromethyl)pyridine (167 mg, 86% yield) was obtained as a crystalline white solid. MS (ISP): m/z = 292.0 [M+H]+ and 294.2 [M+2+H]+.

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, 4-Bromo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A.; NARQUIZIAN, Robert; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/136603; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1632-83-3, 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. 1632-83-3, name is 1-Methylbenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a flame-dried reaction tube was added 1,3-azoles (0.5 mmol, 1.0 eq), 1,10-phenoline (0.5 mmol, 1.0 eq), LiOtBu (1.0 mmol, 2.0 eq), CuBr2 (0.10 mmol, 0.2 eq) and iodine (0.75 mmol, 1.5 eq). Dry 1,4-dioxane (2 mL) was added to the mixture and the mixture was heated to 80C by putting the reaction tube to a preheated oil bath until the products were not increased. The mixture was cooled to room temperature and filtered through a short pad of silica gel. The silica gel was washed with EtOAc (20 mL) and the combined the organic phase was concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography to afford the iodination product.

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

Reference:
Article; Zhao, Xia; Ding, Fang; Li, Jingyu; Lu, Kui; Lu, Xiaoyu; Wang, Bin; Yu, Peng; Tetrahedron Letters; vol. 56; 3; (2015); p. 511 – 513;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, molecular formula is C12H14N2O2, 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. 152628-03-0.

Methyl-6-carboxybenzimidazole 5. 00 kg, methylene chloride 15. 00 kg A solution of 3. 28 kg of thionyl chloride was added dropwise under stirring at 25 C with stirring. Reaction 1 hour, spare

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WEITE(Hunan)Pharmaceutical co.,ltd,; he, liang; Luo, Hui; Mo, Wei; (9 pag.)CN105237457; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

46006-36-4, 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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

(3-Methylbenzoimidazol-4-yl)-(l-methyl-lH-spiro[chromeno[4,3- c]pyrazole-4,4′-piperidine]-l’-yl)methanone [00562] Step 1: (lH-Benzo[d]imidazol-4-yl)(l-methyl-lH-spiro[chromeno[4,3- c]pyrazole-4,4′-piperidine]-l’-yl)methanone To a solution of l-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (211 mg, 0.830 mmol), lH-benzimidazole-4-carboxylic acid (134 mg, 0.830 mmol) and triethylamine (346 mu, 2.50 mmol) in dichloromethane (2 mL) was added HATU (314 mg, 0.830 mmol) in one portion and the mixture was stirred for 12 hours. The reaction mixture was treated with 1M NaOH (1 mL) for 10 minutes. Dichloromethane (5 mL) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (2 x 5 mL). The organic layers were combined, washed with brine, dried over MgSC^, filtered and evaporated to yield a residue that was purified on silica using a gradient of 0.5-30% MeOH in dichloromethane to yield (lH-benzo[d]imidazol-4-yl)(l -methyl- lH-spiro[chromeno[4,3-c]pyrazole-4,4′- piperidine]-l’-yl)methanone. ESI-MS m/z calc. 399.5, found 400.5 (M+l)+. Retention time: 1.12 minutes (4 min run).

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; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara, Sabina; KALLEL, Edward, Adam; MILLER, Mark, Thomas; PONTILLO, Joseph; ANDERSON, Corey; NUMA, Mehdi; FRIEMAN, Bryan, A.; BEAR, Brian, Richard; ARUMUGAM, Vijayalaksmi; HILGRAF, Nicole; MCCARTNEY, Jason; GROOTENHUIS, Peter, Diederik Jan; JOHNSON, James, Philip; WO2011/140425; (2011); 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 3034-50-2 as follows. 3034-50-2

1H-Imidazole-4-carbaldehyde (45.2g, 0.47M) and acetonitrile (0.8 liter) are introduced into a 2 liter flack and cooled to 8C, then TRT-Cl (13 lOg, 0.47M) was added at 8C and TEA (57.lg, 0.56M) was added dropwise during 20 mm. The reaction mixture was stirred at 8 to 18C for 2 hrs.The reaction mixture was poured into a stirring mixture of water (0.72 liter) and MTBE (0.72 liter) and stirred for 10 minutes. The resulting solid was isolated by filtration on Buchner funnel and dissolved with THF (3 liter). The solution was dried over Na2504 and concentrated to remove most of the solvent.MTBE (400 ml) and PE (200m1) was added to the residue, the mixture stirred at 8C for 16 hrs. The precipitated solid was isolated by filtration on Buchner filter and dried in air for 16 hrs at room temperature. Then the filter cake is dried by azeotropic drying with 2-Me-THF (2×500 ml) to give 129g of intermediate 2 as white solid with a yield of 66.5%.

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CLEXIO BIOSCIENCES LTD.; FRENKEL, Anton; IOFFE, Vladimir; (54 pag.)WO2020/16827; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem