Tag: M.W=0-100

Reference of 288-32-4, These common heterocyclic compound, 288-32-4, name is 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.

To a solution of imidazole 9A (20 g, 294 mmol) in THF (200 mL) and TEA (40 g, 400 mmol) was added dimethylsulfamoyl chloride (55 g, 383 mmol) slowly at 0 C. The mixture was stirred at room temperature overnight. The reaction mixture was poured into 300 mL of water and extracted with ethyl acetate (3x). The solution was washed with water and brine, dried over Na2S04, then concentrated to dryness to give compound 9B (42 g, 89%) as a colorless oil, which solidified after standing at room temperature for 1 h. The solid material was used directly in the next step without further purification. 1H NMR (400 MHz, CDC13) delta 7.86 (s, 1H), 7.23 (s, 1H), 7.11 (s, 1H), 2.82 (s, 6H).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily, M.; WRASIDLO, Wolfgang; WO2015/116663; (2015); A1;,
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

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. 930-62-1, name is 2,4-Dimethylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,4-Dimethylimidazole

A solution of methyl mesylate (25.4 mL, 300 mmol) in acetone (50 mL) was added dropwise to a stirred mixture of 2,4-dimethylimidazole (25.00 g, 260 mmol), potassium carbonate (55.20 g, 400 mmol) and acetone (500 mL). Stirring under argon was then continued at room temperature for 16 hours. The resulting solid was filtered off, and the solvent was removed under reduced pressure. The residue was triturated with THF (200 mL) to give crystalline product (59-3) (14.47 g, 25% yield).The filtrate was treated with activated charcoal, filtered through a layer of Celite, and the solvent was removed under reduced pressure. Upon storage of the residue at room temperature, some crystalswere formed, and these crystals were separated, washed with THF and dried in a vacuum oven to give1,2,4-trimethylimidazole (59-1) (4.01 g, 14% yield). Concentration of the filtrate gave a mixture of isomeric imidazoles (59-1) and (59-2) (12.19 g, 43% 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 930-62-1.

Reference:
Patent; NITTO DENKO CORPORATION; STANISLAW, Rachwal; HU, Yufen; ZHANG, Hongxi; (0 pag.)WO2018/161025; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 57090-88-7, 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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2-bromo-l-(2,4-difluorophenyl)ethanone (63.1 g, 269 mmol) and 4-cyano- IH- imidazole (25.0 g, 269 mmol, 1.0 eq) in acetonitrile (200 mL) was added NN-diisopropylethylamine (93.81 mL, 69.4 g, 537 mmol, 2.0 eq) and zinc(II) chloride (3.66 g, 26.86 mmol, 0.10 eq) at 30C. The reaction mixture was stirred at 70 C for 12 hours. The reaction mixture was filtered and concentrated in vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate =1 :1) to give a mixture of desired 3-[2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile and its regioisomeric by-product 1- [2-(2,4-difluorophenyl)-2-oxo-ethyl]imidazole-4-carbonitrile as an approximately 40:60 mixture (total : 30.0 g, combined yield: 45%).

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, 1H-Imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; MILLER, Ricarda; GENIX, Pierre; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; (124 pag.)WO2018/60074; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 288-32-4, 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. 288-32-4 name is 1H-Imidazole, 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.

To a mixture of 1H-Imidazole (50 g, 0.73 mol) in DMF (200 mL) was added NIS (328 g, 1.46 mol) portionwise, the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was poured in sat. Na2CO3 solution, filtered, the residue was washed with water and dried to give 150 g of 2,4,5-triiodo-1H-imidazole (Yield=46%).

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

Reference:
Patent; Genentech, Inc.; US2012/245144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10111-08-7, name is Imidazole-2-carboxaldehyde, 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 10111-08-7, COA of Formula: C4H4N2O

Example 7 Ethyl (2-formyl-1H-imidazol-1-yl)acetate To 1H-imidazole-2-carboaldehyde (2.0 g), N-methylpyrrolidone (25 mL) was added, followed by dissolution with heating. To the resultant solution, ethyl chloroacetate (11.1 mL) and potassium carbonate (2.9 g) were added. The reaction solution was srirred at room temperature for 14 hours. To the reaction solution, water (30 mL) was added. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated saline and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration and the solvent was conentrated under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane) to obtain the title compound having the following physical properties (1.3 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Imidazole-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP2042503; (2009); 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 1072-62-4 as follows. SDS of cas: 1072-62-4

EXAMPLE 2 2-Ethyl-4,5-dihydroxymethylimidazole The procedure described in Example 1 is followed, except that 96 g (1 mole) of 2-ethylimidazole are used instead of 2-methylimidazole. The 155 g of crude product obtained in this procedure are stirred with 52 g of methanol for 30 minutes at 50 C. and at 10 C. with cooling. The mixture is filtered, the product is washed with twice 150 ml of acetone and dried in a drying oven, and 117.5 g of 2-ethyl-4,5-dihydroxymethylimidazole of melting point 173.35-174.0 C. are obtained. This corresponds to a yield of 75.4%. The purity of this sample is 99.8% according to HPLC. Elemental analysis: Mass spectrum: M+ 156. 1 H-NMR spectrum (solvent DDMSO) 1.15 (t, 1p) 2.55 (q, 2p) 4.4 (s, 4p).

According to the analysis of related databases, 1072-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US4658035; (1987); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 57090-88-7, A common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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 round bottom flask was added NaH (60percent in mineral oil) (200 mg, 5.22 mmol) in dry THF (12 ml), followed by the addtion of 1H-imidazole-4-carbonitrile (400 mg, 4.3 mmol), SEMCl (1433 mg, 8.6 mmol). The reactiom mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtO Ac/sat. NaHCO3. The organic phase was separated, washed with water, brine, dried over anhy. Na2SO4, filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel (0-3percent MeOH/CH2Cl2). The product fractions were collected and concentrated to afford 355 mg of 1-(2-trimethylsilanyl- ethoxymethyl)-1H-imidazole-4-carbonitrile, m/z 224.6 [M+l]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); 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. 3034-50-2, name is Imidazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N2O

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 % 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, 82%). The 1H and 13C NMR spectra were consistent with the assigned structure.

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

Related Products of 288-32-4, The chemical industry reduces the impact on the environment during synthesis 288-32-4, name is 1H-Imidazole, I believe this compound will play a more active role in future production and life.

A solution of 68 g of imidazole in 250 cm3 of dimethylformamide was added over 30 minutes to a suspension of 30 g of sodium hydride (at 50% in mineral oil) in 250 cm3 of dimethylformamide. The mixture was stirred for 90 minutes at a temperature in the region of 20 C. and then a solution of 50.5 g of 2-chloroethanol in 50 cm3 of dimethylformamide was added over one hour. The mixture was stirred for 12 hours at a temperature in the region of 20 C. and then filtered. The filtrate was treated with 100 cm3 of distilled water and then concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 55 C. The pasty residue was taken up in 150 cm3 of petroleum ether, the liquid phase was separated by settling and the residue was triturated for one hour with 100 cm3 of isopropanol. The precipitate formed was filtered off and the filtrate was concentrated under reduced pressure (2.7 kPa) at a temperature in the region of 40 C. The residual oil (113.1 g) was distilled under reduced pressure (5 kPa) and resulted in 105.7 g of 2-hydroxy-(1-imidazolyl)ethane in the form of a yellow oil that distilled at a temperature of 180-183 C. at 5 kPa.

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, 1H-Imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rhone-Poulenc Rorer, S.A.; US5965527; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem