Category: imidazoles-derivatives

Synthetic Route of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

[1122] to a mixture of ethyl 1H-imidazole-2-carboxylate (5 g, 35.7 mmol) and phenylboronic acid (8.7 g, 71.4 mmol) in dce (150 ml) was added Cu(OAc)2 (7.13 g, 39.25 mmol), pyridine (5.64 g, 71.36 mmol, 5.76 ml), 4a° ms (3 g). The mixture was stirred at 60 °C for 16 hours under 02. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography eluted with petroleum ether: ethyl acetate = 10: 1, 4: 1 to give compound 221a (3 g, 13.9 mmol, yield: 38.9percent) as a yellow solid. Compound 221a: 1H NMR (400mhz, CDCl3 delta 7.43- 7.39 (m, 3h), 7.27 – 7.23 (m, 2h), 7.22 – 7.19 (m, 1h), 7.11 (d, / = 1.0 hz, 1h), 4.22 (q, = 7.2 hz, 2h), 1.24 (t, j = 7.2 hz, 3h).

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C13H10N2

4.3.1.8 2-Phenylbenzimidazole 13 Following general procedure A, exchange of 2-phenylbenzimidazole 13 (16.8 mg) in the presence of catalyst 1a (4.4 mg) gave [2′,6′-2H2]-13 (14.8 mg, 88percent, 84percentD). Following general procedure A, exchange of 2-phenylbenzimidazole 13 (16.8 mg) in the presence of catalyst 1b (4.6 mg) gave [2′,6′-2H2]-13 (14.9 mg, 89percent, 83percentD). Following general procedure A, exchange of 2-phenylbenzimidazole 13 (16.8 mg) in the presence of catalyst 1c (3.8 mg) gave [2′,6′-2H2]-13 (13.8 mg, 82percent, 72percentD). Following general procedure A, exchange of 2-phenylbenzimidazole 13 (16.8 mg) in the presence of catalyst 5 (3.4 mg) gave [2′,6′-2H2]-13 (15.3 mg, 91percent, 72percentD). deltaH (300 MHz, DMSO-d6) 12.90 (s, 1H), 8.19-8.17 (m, 2H), 7.60-7.47 (m, 5H), 7.23-7.18 (m, 2H).

The synthetic route of 716-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Atzrodt, Jens; Derdau, Volker; Kerr, William J.; Reid, Marc; Rojahn, Patrick; Weck, Remo; Tetrahedron; vol. 71; 13; (2015); p. 1924 – 1929;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 583-39-1, name is 2-Mercaptobenzimidazole, 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 583-39-1, Quality Control of 2-Mercaptobenzimidazole

A mixture of 1H-benzo[d]imidazole-2(3H)-thione 1 (0.026 mole, 5 gm) in 60 mL ethanol and inpresence of triethylamine (0.01 mol, 1.39 mL) was refluxed for 1 h, then 1,3-dibromopropane (0.013 mol,2.6 g) was added. The reaction mixture was further heated under reflux for 5 h. Then, ethanol wasremoved under vacuum, and water (20 mL) was added to the product, and kept for 24 h at roomtemperature to give white crystals. The product (4.68 g, 83% yield), was recrystallized from ethanol,TLC, Rf = 0.382 (1:1, n-hexane:ethyl acetate), m.p. 201-202 C. 1H-NMR (DMSO-d6) : 2.29 (m, 2H,CH2), 3.26 (t, 2H, CH2), 4.17 (t, 2H, CH2), 7.11 (m, 2H, Ar-H), and 7.39 ppm (m, 2H, Ar-H). 13C-NMR(DMSO-d6) : 21.9 (CH2), 24.3 (CH2), 41.7 (CH2), 107.9 (CH), 116.1 (CH), 120.02 (CH), 120.94 (CH),134.69 (C), 134.81 (C), 141.4; 145.75 ppm (C=N). Calc. for C10H10N2S (190.26): C, 63.13; H, 5.30;N, 14.72%. Found: C, 63.42; H, 5.11; N, 14.41%.

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:
Article; El Ashry, El Sayed H.; Kilany, Yeldez El; Nahas, Nariman M.; Barakat, Assem; Al-Qurashi, Nadia; Ghabbour, Hazem A.; Fun, Hoong-Kun; Molecules; vol. 21; 1; (2016);,
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. 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, A new synthetic method of this compound is introduced below., Computed Properties of C10H12N2O

Step 2 3-[2-(3-Hydroxy-propyl)-benzimidazol-1-yl]-propionitrile To a stirred solution of 3.8 g of 3-(1H-benzimidazol-2-yl)-propan-1-ol and 4 g dihydropyran in 500 mL of THE was added p-toluenesulfonic acid monohydrate until the pH was about 3 (indicator paper). After stirring overnight, an additional 2 mL of dihydropyran was added: After 2 additional hours, the conversion was complete. The mixture was concentrated under reduced pressure and partitioned between 250 mL of 1N NaOH and 2*250 mL of ether. After drying over magnesium sulfate the combined extracts were concentrated to dryness. To a solution of the resulting crude oily 2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-benzimidazole (14 g) in 250 mL of acetonitrile was added 5 mL of acrylonitrile, 2 drops of 1M tetrabutylammonium fluoride in THF and 1 drop 10N NaOH. After heating to 85 C. for 16 h, conversion was complete (TLC elution with 90:10 methylene chloride:methanol). After concentration under reduced pressure, the residue was partitioned between 2*200 mL of ethyl acetate and 200 mL of water. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The crude 3-(2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-benzimidazol-1-yl}-propionitrile was stirred in 250 mL of methanol with sufficient p-toluenesulfonic acid monohydrate to make the solution acidic (pH=1-2). After stirring overnight, the solution was concentrated under reduced pressure, made basic (pH=8) with 1N sodium hydroxide and extracted into 8*50 mL of ethyl acetate. The aqueous layer was saturated with NaCl to aid in extraction of the product. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of ethyl acetate, then 10% methanol in ethyl acetate, followed by trituration with ether-hexane gave 4.8 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile as a solid.

The synthetic route of 2403-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6432976; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Compound 9 (5.534 g, 12.73 mmol) was dissolved inCH2CI2 (14 ml_) in a flamed dried round bottom flask. To this stirring solution was added DMAP (0.1555 g, 1.273 mmol) and TCDI (3.402 g, 19.09 mmol) which dissolved into solution after several hours of stirring. The reaction vessel was sealed with a rubber septum and flushed with argon, and the reaction mixture stirred at room temperature for 3 days. The reaction mixture was then concentrated to provide the crude product as a dark orange viscous oil, which was directly loaded on the silica gel. Compound 10 was isolated as a pale yellow viscous oil via FCC (gradient 30% to 50% EtOAc in hexanes) in 92% yield (6.401 g, 1 1 .75 mmol). Rf = 0.20 (30% EtOAc in hexanes); 1H NMR (300 MHz, CDCI3) delta 8.28 (1 H, s), 7.54 (1 H, s), 6.95 (1 H, s), 5.43 (1 H, dd, J = 8.5, 3.0 Hz), 4.61 -4.54 (2H, m), 4.50-4.41 (1 H, m), 3.70 (3H, s), 2.27- 2.13 (2H, m), 2.04-1.92 (2H, m), 0.82 (9H, s), 0.70 (9H, s), 0.01 (3H, s), 0.00 (3H, s), -0.05 (3H, s), -0.17 (3H, s); 13C NMR (75 MHz, CDCb) delta 183.6, 173.2, 137.0, 130 7, 1 17.7, 86.0, 75.1 , 68.3, 65.4, 52.7, 43.0, 38.0, 25.8, 25.7 (2C), 25.5 (2C), 25.4, 17.8, 17.7, -4.2, -4.7, -4.9, -5.6.

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

Reference:
Patent; McGILL UNIVERSITY; WO2007/131364; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

1. 4-(Imidazol-1-yl)nitrobenzene. To a stirred solution of imidazole (34.1 g, 0.50 mol) in DMF (300 ml) under Ar, was added portionwise, over 23 minutes, 60% NaH in oil (20.02 g, 0.50 mol). The mixture was then stirred at room temperature for 18 minutes before adding dropwise, over 40 minutes, a solution of 1-fluoro-4-nitrobenzene (70.62 g, 0.50 mol) in DMF (60 ml). The mixture was then stirred at room temperature overnight. Water (600 ml) was then added and the solid was filtered off, washed with water, then stirred in boiling ethyl acetate (400 ml), allowed to cool and filtered, washing the solid with more ethyl acetate (50 ml), then petroleum ether (250 ml). The filtrate, now containing more solid, was refiltered and washed with petroleum ether. The combined solids were dried in a vacuum dessicator overnight to give 90.14 g (95%) of the title compound as a yellow solid. deltaH (360 MHz, DMSO-d6) 9 (1H, t, J=1.1 Hz), 7.97-8.03 (3H, m), 8.38 (2H, d, J=9.2 Hz), 8.52 (1H, t).

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, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme, Ltd.; US5854268; (1998); A;,
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. 17289-20-2, name is Methyl 1-methyl-1H-imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H8N2O2

To the solution of commercially available 4.3 g methyl 3-methylimidazole-4-carboxyIate in 100 mL THF at 23 C was added 7.4 g lithium tertbutoxide and reaction mixture was stirred at 23 C for 15 min. Then, 10.9 g N-bromosuccinimide (NBS) was added and reaction mixture was stirred at 23 C for additional 12 h. Reaction mixture was quenched with water and was basified with sat. NaHCC>3 solution to pH 14. The compound was extracted with EtOAc (20 mL x 3), combined organic layer was dried over Na2S04and concentrated under reduced pressure to get crude compound which was purified by column chromatography over silica gel using 30 % EtOAc in />heptane as an eluent to afford the title compound as off white solid (1.8 g; 27.0% yield).

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 17289-20-2.

Reference:
Patent; BASF SE; GOCKEL, Birgit; SOERGEL, Sebastian; KOERBER, Karsten; (152 pag.)WO2019/137995; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 51605-32-4, 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 51605-32-4 as follows.

Hydrolysis of ethyl-4-methyl-1H-imidazole carboxylate(7, 3.0 g, 19.5 mmol) was carried out in a basic medium offreshly prepared 2 M NaOH solution for 3 h. Neutralizationwith glacial acetic acid was performed after the completionof the reaction. The aqueous solvent was evaporated underreduced pressure and 10 mL of absolute ethanol was used tore-dissolve the white solid product. The reaction mixture wasfiltered off and the precipitate was dissolved several timeswith absolute ethanol and co-evaporation was performed toremove water traces. 4-Methyl-1H-imidazole-5-carboxylic acid(8) was obtained as a white solid with a yield of 87.8%.

According to the analysis of related databases, 51605-32-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jasim, Suhair H.; Sheikha, Ghassan M. Abu; Abuzaid, Haneen M.; Al-Qirim, Tariq M.; Shattat, Ghassan F.; Sabbah, Dima A.; Ala, Samah A.; Aboumair, Mustafa S.; Sweidan, Kamal A.; Bkhaitan, Majdi M.; Chemical and Pharmaceutical Bulletin; vol. 66; 10; (2018); p. 953 – 958;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, 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. Recommanded Product: 1-Ethyl-1H-imidazole

To the dry 100 mL three-necked flask was added 6.3 g (10 mmol) of M2 ‘, 0.96 g (10 mmol) of 1-ethyl terephthalate, 50 mL of acetonitrile, reacted at room temperature for 4 days and TLC was used to monitor the reaction end. Washed with petroleum ether (100 mL x 3) to give a viscous liquid which was washed with ether (100 mL x 3), dried in vacuo for 24 h, To give 7.2 g of the title compound (B5) as a brown oily liquid in a yield of 99percent.

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

Reference:
Patent; Central China Normal University; Zhang Aidong; Zhang Tiejiang; Duan Jiang; Tu Haiyang; (22 pag.)CN107188869; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1457-58-5, The chemical industry reduces the impact on the environment during synthesis 1457-58-5, name is 2-Methyl-1H-imidazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

a) (S)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-methyl-1H-imidazole-4-carboxamide 2-Methyl-1H-imidazole-4-carboxylic acid (29.0 g, 230 mmol), 335 ml of DMF and 165 ml of DCM were placed in to the reaction vessel under nitrogen. HBTU (7.27 g, 19.18 mmol), EDCI (44.1 g, 230 mmol) and 66.8 ml of DIPEA were added. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (50 g, 192 mmol) was added and the reaction stirred overnight at RT. 600 ml of water was slowly added and water phase was washed with 335 ml and 500 ml of DCM. DCM phases were combined, washed with 3*600 ml of water and distilled to dryness. Acetonitrile (300 ml) was added and the mixture was heated up to 75 C. Water (300 ml) was added at >60 C., solution was allowed to cool to RT for precipitation and the mixture was stirred overnight at RT. Stirring was continued for additional 2 h at <10 C. The precipitate was filtered, washed with cold ACN:water and dried under vacuum to obtain 47 g of crude product. The title compound was recrystallized from EtOH with 75% yield. 1H-NMR (400 MHz, DMSO-d6): delta 1.08 (d, 3H), 2.30 (s, 3H), 4.23-4.48 (m, 3H), 6.95 (d, 1H), 7.41 (s, 1H), 7.82 (d, 1H), 7.95-8.07 (m, 3H), 8.09-8.12 (m, 1H), 12.12 (bs, 1H). 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-Methyl-1H-imidazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem