Month: June 2021

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

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

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

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

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

Adding a certain compound to certain chemical reactions, such as: 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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 32673-41-9, Product Details of 32673-41-9

Step B 4-Hydroxymethyl-1-triphenylmethylimidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitates from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product which is sufficiently pure for use in the next step.

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; Merck & Co., Inc.; US5891889; (1999); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of Imidazole-4-carbaldehyde

Example 72An alternate method’for the synthesis of the imidazole intermediate is described below:4-Cyano-l-(2-trimethylsilanyl-ethoxymethyl)-lH-imidazole-2-carboxylic acid potassium salt a) lH-Imidazole-4-carbonitrile; ‘-NHA 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, a condenser, and an addition funnel with a nitrogen inlet was charged with lH-imidazole-4-carboxaldehyde (Aldrich, 1.10 kg, 11.5 mol) and pyridine (3.0 L, 3.0 mol). The reaction flask was cooled to 8 0C with an ice bath and hydroxylamine hydrochloride (871 g, 12.5 mol) was added slowly in portions to maintain the internal temperature below 30 °C. The reaction was allowed to cool to ambient temperature and stirred for 2 h at ambient temperature. The resulting thick yellow solution was heated to 80 0C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise EPO over 200 min to maintain the temperature below 110 °C during the addition. The reaction mixture was heated at 100 0C for 30 min, after which time it was allowed to cool to ambient temperature and then further cooled in an ice bath. The pH was adjusted to 8.0 (pH meter) by the addition of 25 wt percent NaOH (5.5 L) at such a rate that the internal temperature was maintained below 30 °C. The reaction mixture was then transferred into a 22-L separatory funnel and extracted with ethyl acetate (6.0 L). The combined organic layer was washed with brine (2 x 4.0 L), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure at 35 °C to give the crude product as a yellow semisolid. The resulting semisolid was suspended in toluene (3.0 L) and stirred for 1 h, after which time it was filtered to give a light yellow solid, which was resuspended in toluene (3.0 L) and stirred for 1 h. The resulting slurry was filtered and the filter cake washed with toluene (2 x 500 mL) to give the title compound as a light yellow solid [870 g, 82percent). The 1H and 13C NMR spectra were consistent with the assigned structure.

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 3034-50-2.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47504; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3034-42-2,Some common heterocyclic compound, 3034-42-2, name is 1-Methyl-5-nitroimidazole, molecular formula is C4H5N3O2, 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 2 1-Methyl-2-hydroxymethyl-5-nitroimidazole 27.9 g. of 1-methyl-5-nitroimidazole prepared as in Example 1 and 30.1 g. of paraformaldehyde are added to 154 ml. of dimethylsulfoxide and the resulting solution is sealed into a glass-lined tube. The solution is heated at 110 C. for 24 hours, with shaking. The dimethylsulfoxide is removed by distillation at 53-56 C./2 mm. The residue is extracted with 3 * 150 ml. of hot benzene. The benzene extracts are combined and cooled to room temperature. 1-Methyl-2-hydroxymethyl-5-nitroimidazole crystallizes, and is recovered by filtration. The yield of product is 23 g., m.p. 112-114.5 C. When 1-ethyl-5-nitroimidazole, 1-propyl-5-nitroimidazole, 1-n-butyl-5-nitroimidazole, and 4(5)-nitroimidazole are used in the above reaction, respectively, the following compounds are prepared: 1-ethyl-2-hydroxymethyl-5-nitroimidazole; 1-propyl-2-hydroxymethyl-5-nitroimidazole; 1-n-butyl-2-hydroxymethyl-5-nitroimidazole; and 2-hydroxymethyl-5-nitroimidazole.

The synthetic route of 3034-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US4010176; (1977); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 23814-14-4, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid, 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 23814-14-4, Quality Control of 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylic acid

C) 2-Oxo-2, 3-dihydro-lH-benzoimidazolyl-5-carboxyl (I-N-3, 4- dibenzyloxy phenyl) amide; 1, 3- N, N-Diisopropylcarbodiimde (0.412 g; 3.27 mmol) was added to a solution of 2-oxo-2, 3-dihydro-1H-benzoimidazole-5-carboxylic acid (0.584 g; 3.27 mmol) 3,4-dibenzyloxy aniline (1.0 g, 3.27 mmol) and 1-hydroxybenzotriazole (0.442 g, 3.27 mmol) in anhydrous N, N – dimethylformamide (15 ml). After stirring for 16 hrs at room temperature the reaction mixture was poured in water (150 ml). The pH of the mixture was adjusted to 2 with IN hydrochloric acid and stirred for 30 minutes. Filtration and washing the product with ethyl acetate (3 x 10 ml) provided 1.12 grams of 2-Oxo-2, 3-dihydro-l H-benzoimidazolyl-5-carboxyl (1-N-3, 4-dibenzyloxy phenyl) amide. Yield = 73.6 %. ¹H NMR (CD3)2SO 10.5 (1H, s, NH) 7.65 (1H, d, J 8Hz) 7.6 (1H, s) 7.2-7.6 (m, 12H) 7.0 (2H, d, J 8Hz) 5.15 (4H, s).

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; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem