Month: June 2021

Reference of 939-70-8, A common heterocyclic compound, 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, molecular formula is C9H8N2O, 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.

General procedure: Various o-substituted anilines (0.05 mol) and lactic acids (3.75 mL, 0.05 mol) were dissolved in 20 mL of HCl (4 M). The mixture was heated under reflux for 1.5 h. After cooling to room temperature, the reaction mixture was poured into water. Next, the pH was adjusted to 10-11 with ammonia. The mixture was filtered, and the residue was recrystallized from water to give intermediates 1b-3b. Next, 1b-3b (0.02 mol) were each dissolved in 15 mL of acetic acid. When the mixture was heated to 90 C, chromium trioxide solution was added. The reaction mixture was stirred at 105C for 30 min. After cooling to room temperature, the reaction mixture was poured into water (1 L) and then extracted by ethyl acetate (EtOAc). The organic layers were combined, dried with MgSO4, filtered and then concentrated under reduced pressure. The residue was recrystallized from toluene to give the intermediates 1c-3c. Last, 1c-3c (0.02 mol) and 8 mL of a 10% NaOH aqueous solution were dissolved in 20 mL of ethanol. The reaction mixture became a clear red solution. Next, various substituted aromatic aldehydes (0.02 mol) were added. After stirring for 5 h, the mixture was filtered, and the residue was purified by column chromatography (EtOAc: hexane = 1:5) to give the target compounds A1-A13, B1-B3 and C1-C3.

The synthetic route of 939-70-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Lin-Tao; Jiang, Zhi; Shen, Jia-Jia; Yi, Hong; Zhan, Yue-Chen; Sha, Ming-Quan; Wang, Zhen; Xue, Si-Tu; Li, Zhuo-Rong; European Journal of Medicinal Chemistry; vol. 114; (2016); p. 328 – 336;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-13-3, 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 641571-13-3 as follows.

General procedure: A mixture of compound 6a (20.0 mg, 0.06 mmol), 3-trifluoromethyl-benzoic acid (23.11 mg, 0.12 mmol), HOBt (18.1 mg, 0.13 mmol), and EDCI (29.1 mg, 0.15 mmol) in dry DMF (1.0 mL) was cooled to 0 C under nitrogen atmosphere. To the reaction mixture, triethylamine (0.002 mL, 0.015 mmol) was added at 0 C. The mixture was then stirred at 80 C for 12 h. The reaction mixture was cooled and then partitioned between water (5 mL) and ethyl acetate (5 mL) and the organic layer was separated. The aqueous layer was then extracted with ethyl acetate (3 × 3 mL) and the combined organic extracts were washed with brine and dried over anhydrous Na2SO4. After evaporation of the organic solvent, the residue was purified by column chromatography (silica gel, hexane-ethyl acetate 3:1 v/v then switching to hexane-ethyl acetate 1:1 v/v) to yield compound 9a (5.0 mg, 16.4%).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; El-Gamal, Mohammed I.; Jung, Myung-Ho; Lee, Woong San; Sim, Taebo; Yoo, Kyung Ho; Oh, Chang-Hyun; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3218 – 3226;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]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 28890-99-5, Application In Synthesis of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

Example 6 a) 20.0 g (78.8 mmol) 1,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H-benzimidazolo[1,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61%).1H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

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; BASF SE; US2012/241681; (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

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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H10N2O

a.) 21.0 g (100 mmol) 3-phenyl-1H-benzimidazol-2-one and 24.2 g (110 mmol) 4-bromo-2- fluoro-1-nitro-benzene, 27.6 g (200 mmol) potassium carbonate in DMF is stirred at 100 C for 20 h. The reaction mixture is poured in water and the water phase is extracted with (0803) dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is removed in vacuum. Yield 23 g (56 %) 1H NMR (400 MHz, CDCl3): ^ = 8.11 (d, 1H), 7.92 (d, 1H), 7,79 (dd, 1H), 7.55.7.61 (m, 4H), 7.44-7.48 (m, 1H), 7.15-7.21 (m, 3H), 7.00-7.05 (m, 1H).

According to the analysis of related databases, 14813-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (320 pag.)WO2017/56053; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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. HPLC of Formula: C7H10N2O2

To an oven- dried three-neck reaction flask charged with a magnetic stir bar, an internal thermometer at rt under argon was added ethyl 4-methyl-lH-imidazole-5- carboxylate (2.20 g, 14.3 mmol) and anhydrous DMF (71 mL). The yellow solution was cooled to -20C using a dry ice and EtOAc bath. Lithium hexamethyldisilane (1.0M in TetaF, 15.7 mL, 15.7 mmol) was then added dropwise via an addition funnel while maintaining the internal temperature below -12C. To the solution was then added o-(diphenylphosphinyl)- hydroxylamine (4.00 g, 17.1 mmol) in two portions while maintaining the internal temperature at O0C. The resulting white suspension was diluted by the addition of DMF (15 mL) and stirred at rt overnight. The white suspension was quenched with water (5 mL) and the solvent was removed under vacuum. The resulting yellow solid was extracted with CH2Cl2 (50 mL), EtOAc (100 mL) and then the organic extracts were combined and concentrated by rotary evaporation to a brown solid. It was purified by flash column chromatography (80 g pre-packed silica gel column, gradient elution with CH2Cl2, to CH2Cl2:Me0H, 4:96) to give 1.00 g (41%) of the title compound as a white solid. 1H NMR (CDCl3) 7.59 (s, I H), 5.32 (br s, 2H), 4.36 (q, J= 7.1 Hz, 2H), 2.45 (s, 3H), 1.40 (t, J= 7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51605-32-4, its application will become more common.

Reference:
Patent; CYTOVIA, INC.; WO2008/57402; (2008); A2;,
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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1-Decyl-1H-imidazole

General procedure: A solution of 1,3-propane sultone (1.34 g, 0.011 mol) in acetone (12 mL) was slowly added to the flask containing the akyl imidazole (0.012 mol) at 0 C. The reaction mixture was heated to the room temperature and, then, stirred for 5 days. After that, the reaction solution was filtrated giving the product as a solid. The solid was washed two times with a mixture of 1:1 hexane/dichloromethane and driedunder vacuum, giving the zwitterionic surfactant in 51% yield. The given product was characterized by 1H-NMR in CDCl3.

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:
Article; Modenez, Iago A.; Sastre, Diego E.; Moares, Fernando C.; Marques Netto, Caterina G.C.; Molecules; vol. 23; 9; (2018);,
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

Electric Literature of 870837-70-0, The chemical industry reduces the impact on the environment during synthesis 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, I believe this compound will play a more active role in future production and life.

l-(4-Ethynyl-2-methoxyphenyl)-l//-imidazole.A mixture of 4-fiuoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130 C. Stirred overnight. Diluted with EtOAc, washed with sat’d NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (l-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), cone. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:1H NMR (600 MHz, CDCl3) delta7.79 (s, 1 H), 7.18 (t, J= 1.2 Hz, 1 H), 7.16 (d, J= 1.8 Hz, 1 H), 7.15 (m, 2 H), 7.13 (d, J= 1.5 Hz, 1 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-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/156580; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]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. category: imidazoles-derivatives

General procedure: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 5-Methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem