Category: imidazoles-derivatives

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

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

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

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

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

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

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. 35203-44-2, name is 1-Propyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Propyl-1H-imidazole

Part of the trans-[RuCl4(DMSO)2]Na 0.10g (0.24mmol) prepared in Example 1 was dissolved in acetone andTo 0.33 ml of dimethyl sulfoxide, 0.14 ml (1.23 mmol) of N-propylimidazole was further added. The ultrasonic reaction was carried out for 2 hours. The reaction liquid was filtered, and a mixture of chloroform and diethyl ether was added to the filtrate to cause crystallization. The crystals were filtered, washed with a mixture of chloroform/diethyl ether (v/v = 1:9) and dried over silica gel to give the desired product G99. Yield: 70percent.

According to the analysis of related databases, 35203-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Zhongyi Academy Of Sciences Traditional Chinese Medicine Institute; Beijing Tangshi Traditional Chinese Medicine Research Center; Gu Liwei; Liang Yaohua; Li Canghai; Shen Jianying; Liang Guogang; Jiang Tingliang; Li Xiaodong; (16 pag.)CN104744518; (2018); B;,
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

75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. SDS of cas: 75370-65-9

Amine 2bf (1.1 g, 6.7 mmol) was dissolved in 40ml of AcOEt and at0C triphosgene (1.93 g, 6.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 15ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (1 g, 6.7 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 450 mg of a pale yellow solid. Yield = 19% ‘HNMR (DMSO, 200 MHz) delta 2.26 (3H, s), 2.59 (6H, m), 4.33 (2H, d, J = 5.6 Hz), 6.60 (2H, m), 6.87 (4H, m), 7.18 (1H, d, J = 7.6 Hz), 8.28 (1H, s), 9.96 (1H, bs), 10.60 (1H, bs); [M+1] 339.56 (C18H21N5O2 requires 339.39).

The synthetic route of 75370-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 38993-84-9, 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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 32C 1-methyl-1H-imidazole-5-carbaldehyde A solution of Example 32B (2.3 g, 20 mmol) in dioxane (100 mL), was treated with manganese dioxide (17.3 g, 200 mmol), heated to reflux for 16 hours, cooled to room temperature, filtered through a pad of diatomaceous earth (Celite), and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. 1H NMR (300 MHz, CDCl3) delta 9.77 (d, 1H), 7.79 (s, 1H), 7.62 (s, 1H), 3.95 (d, 3H).

The synthetic route of (1-Methyl-1H-imidazol-5-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Wei-Bo; Curtin, Michael L.; Fakhoury, Stephen A.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Hutchins, Charles W.; Li, Qun; Lin, Nan-Horng; Nelson, Lissa Taka Jennings; O’Connor, Steve; Sham, Hing L.; Sullivan, Gerard M.; Wang, Gary T.; Wang, Xilu; US2002/19527; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem