Tag: M.W=0-100

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., Formula: C5H8N2

Copper oxide (0.045 g, 0.316 mmol), 4,7-bis(methyloxy)-1 ,10-phenanthroline (0.228 g, 0.948 mmol), polyethylene glycol (1.248 g, 11.76 mmol), cesium carbonate (2.88 g, 8.84 mmol), 2,4-dimethyl-1 H-imidazole (0.729 g, 7.58 mmol) and 1 ,1-dimethylethyl3-chloro-5-iodobenzoate (D53, 2.139 g, 6.32 mmol) were transferred into a dried round-bottomed flask vial and capped with a rubber septum. The flask was then evacuated and backfilled with argon – this process was repeated several times. Butyronitrile (3.12 ml.) was then added and the mixture was stirred at 80 0C overnight during which time the reaction had evaporated to dryness. Further butyronitrile (3.12 ml.) was added and the mixture stirred at 80 0C over the weekend.The mixture was diluted with dichloromethane and then filtered through celite. The filtrate was concentrated in vacuo and the resulting crude material (2.8 g) was purified by flash chromatography with a gradient of 0 – 100% ethyl acetate in hexane to afford the title compound as a white solid.LC/MS (ES+ve): [M+H]+ at m/z 307, 309 (C16H19CIN2O2 requires [M+H]+ at m/z 307, 309)

According to the analysis of related databases, 930-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/819; (2008); 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.

To a 1000 ml flask were added 108.3 g (1.59 mol) of imidazole and 630 g of tetrahydrofuran. After the atmosphere of the system was replaced with nitrogen, the imidazole was dissolved under stirring. Thereto was added dropwise 39.3 g (0.2 mol) of diphosgene at room temperature over a period of 2 hours. After completion of the dropwise addition, the stirring was continued at room temperature for 1 hour and then the whole was heated to 55C, followed by continuous stirring for another 1 hour. Imidazole hydrochloride yielded as a by-product was filtrated with heat and was then washed with 100 g of tetrahydrofuran. The imidazole hydrochloride filtrated off was dried under reduced pressure at 40C to obtain 83.2 g (0.796 mol) of imidazole hydrochloride (recovery of 100%). A filtrate containing CDI was concentrated and subjected to toluene-crystallization, and CDI was filtrated off under a nitrogen atmosphere. The CDI filtrated off was dried under reduced pressure at 40C to obtain 58.0 g (0.358 mol) of CDI as white crystals (yield 90%). M.p. 111.2 to 118.6C.

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; Hodogaya Chemical Co., Ltd.; EP1731510; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

616-47-7, name is 1-Methyl-1H-imidazole, 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. HPLC of Formula: C4H6N2

1-Methyl-1H-imidazole (20 g, 244 mmol) was dissolved in anhydrous THF (200 mL) under a nitrogen atmosphere. The solution was stirred at -78 C and n-BuLi (167 mL, 268 mmol) was added dropwise slowly at -78 C. After 1 h, CBr4 (97 g, 292 mmol) solution in anhydrous THF (200 mL) was added. The solution was stirred for 2 h at -78 C and for 1 h at room temp. The reaction mixture was quenched with saturated aqueous ammonium chloride (300 mL), extracted with ethyl acetate (2 x 200 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude compound was purified by silica gel chromatography eluting with 60% ethyl acetate in pet. ether to afford the title compound. LCMS (method B): rt = 1.89, [M+H]+= 161.

The synthetic route of 616-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BARTON, Nicholas Paul; BERTRAND, Sophie Marie; DOWN, Kenneth; GRAY, Matthew; (168 pag.)WO2019/141694; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 stirred solution of 2-chloro-3-methoxy-5-nitropyridine (1.5 g, 79.78 mmol) in DMSO (15 mL) under an argon atmosphere were added potassium carbonate (4.4 g, 31.91 mmol) and 1H-imidazole-4-carbonitrile (890 mg, 9.57 mmol) at room temperature. The reaction mixture was stirred at 50 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (20 mL). The obtained solid was filtered and dried in vacuo to obtain 1-(3-methoxy-5-nitropyridin-2-yl)-1H-imidazole-4- carbonitrile (1.1 g, 56percent) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.97 (s, 1H), 8.86 (s, 1H), 8.67 (s, 1H), 8.47 (s, 1H), 4.11 (s, 3H); LCMS: 245.8 (M+1); (column; X-Select CSH C-18 (50 × 3.0 mm, 3.5 mum); RT 2.96 min. 0.05percent aq TFA: ACN; 0.80 mL/min); TLC: 40percent EtOAc:hexane (Rf: 0.4).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1072-62-4, name is 2-Ethyl-1H-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 1072-62-4, SDS of cas: 1072-62-4

The 400mg4-amino-6-chloro-pyrimidine, 317 mg (1.1equiv) 2-ethyl imidazole, 1.2g (1.2equiv) adding cesium carbonate flask, 10mLN, N ‘-dimethyl formamide as a solvent, the temperature is increased to 120 C, reaction 18h. Adding proper amount of water, extraction with ethyl acetate, saturated salt water washing, drying by anhydrous sodium sulfate, filter, evaporate solvents under reduced pressure, the residue is purified by silica gel column chromatography separation, methanol/dichloromethane = 1/30 elution, to get the yellow solid 105 mg, yield 18%.

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; East China University of Technology; Mao, Fei; Wang, Huan; Li, Xiaokang; Zhang, Haiyan; Lu, Zhengyu; Li, Jian; (43 pag.)CN105418592; (2016); A;,
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 616-47-7 as follows. HPLC of Formula: C4H6N2

(Reference Example 9) Synthesis of ethyl 1-methyl-1H-imidazole-2-carboxylate: Triethylamine (3.40 mL, 24.4 mmol) and ethyl chloroformate (2.34 mL, 24.4 mmol) were added to a solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol) in acetonitrile (4.0 mL) at 0C and the reaction liquid was stirred at room temperature for 16 hours. The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 1.42 (3H, t, J=7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J=7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m). ESI-MS: m/z= 155 (M+H)+.

According to the analysis of related databases, 616-47-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-50-2, name is Imidazole-4-carbaldehyde, 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 3034-50-2, Computed Properties of C4H4N2O

A 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 C 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 C with a heating mantle and acetic anhydride (2.04 L, 21.6 mol) was added dropwise over 200 min to maintain the temperature below 110 0C during the addition. The reaction EPO 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 0C 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.

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; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1. To a solution of 1 (20 g, 108.1 mmol) in dry DMF (200 mL) were added lH-imidazole (8.1 g, 118.9 mmol), Cs2C03 (38.7 g, 118.9 mmol), Cul (2 g), 18-Crown-6 (2 g). The resulting solution was stirred at 80 C for 24 h. The mixture was cooled to RT, treated with water and extracted with EA. The combined extracts were washed with water, brine, dried over anhydrous Na2S04, filtered and concentrated to give a crude oil. The crude product was purified by recrystallization to afford 2 (1 1 g, 59.2 %).

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; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; CHIANG, Lillian W.; MURPHY, Eain Anthony; KAYSER, Frank; SUN, Qun; FINK, Sarah Jocelyn; (128 pag.)WO2019/79519; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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. Application In Synthesis of 1-Ethyl-1H-imidazole

Step 1: 341 parts of 1-ethylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), 319 parts of dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 340 parts of methanol (Tokyo Chemical Industry Co., Ltd.) were charged in a stainless steel autoclave equipped with a reflux condenser, And dissolved. Then, the temperature was raised to 140 ° C. The reaction was carried out at a pressure of 0.8 MPa for 30 hours. 1 H-NMR analysis of the reaction product revealed that 1-ethyl-3-methylimidazolium monomethyl carbonate was formed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7098-07-9, its application will become more common.

Reference:
Patent; SANYO CHEMICAL INDUSTRIES LIMITED; SATOU, YOSHIMI; MURATA, SHINICHI; SEIKE, HIDEO; (20 pag.)JP5848690; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application 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.

Benzoyl chloride (4.99 g, 35.5mmol) wasadded dropwise to a solution of imidazole (4.83 g, 7.1mmol)in dichloromethane (25 mL). The reaction mixture wasstirred for 3 h, and the resulting precipitate was removedby filtration. The filtrate was washed with cold water (<=5 C,10mL x 3) and concentrated under reduced pressure. Theresidue was purified by bulb-to-bulb distillation (heatertemperature: 160 C, 80 mmHg) to yield 1c (4.33 g, 71%yield) as colorless liquid. 1HNMR (400 MHz, CDCl3,26 C): /ppm 8.07 (t, J = 1.0 Hz, 1H, f ), 7.817.79(m,2H, a), 7.69 (tt, J1 = 7.4 Hz, J2 = 1.8 Hz, 1H, c), 7.587.54(m, 3H, b and d), 7.16 (dd, J1 = 1.8 Hz, J2 = 1.0 Hz, 1H, e). The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings. Reference:
Article; Kohsaka, Yasuhiro; Homma, Kazumasa; Sugiyama, Susumu; Kimura, Yoshikazu; Chemistry Letters; vol. 47; 1; (2018); p. 100 – 102;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem