Category: imidazoles-derivatives

Application of 10394-38-4, 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 10394-38-4 as follows.

2.2 N-(1-Methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxamide hydrochloride (1:2) (Compound 4) 4.1 ml of trimethylaluminum (2M in toluene) are added under argon to a solution of 0.414 g (2.82 mmol) of 5-amino-1-methyl-1H-benzimidazole in 10 ml of dry toluene. After 15 minutes, 0.7 g (2.35 mmol) of ethyl 5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxylate, obtained in step 2.1, is added. The reaction medium is refluxed for 4 hours and then stirred overnight at room temperature. It is poured onto 100 g of ice and 50 ml of dichloromethane. A suspension is obtained, which is filtered and washed with water and ether. The residue is purified by preparative chromatography on alumina (eluent: dichloromethane/methanol). 0.36 g of a solid is obtained, which is dried under reduced pressure. The resulting solid is taken up in 30 ml of dichloromethane and 0.55 ml of a 4N solution of hydrogen chloride in dioxane is added. The solution is concentrated under reduced pressure and the resulting solid is recrystallized from a mixture of isopropanol and methanol. 0.36 g of the expected product is thus obtained in the form of a hydrochloride. Melting point (2HCl): 268-270 C. 1H NMR (DMSO D6), delta (ppm): 4.03 (s, 3H); 6 (s, 2H); 7.18 (dxd, 1H); 7.56 (dxd, 1H); 7.68 (m, 2H); 7.9 (m, 4H); 8.41 (s, 1H); 8.69 (m, 2H); 9.59 (s, 1H).

According to the analysis of related databases, 10394-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2008/146646; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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 6775-40-2, Product Details of 6775-40-2

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

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; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
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. 16265-04-6, name is 2-Chloro-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16265-04-6

Reference example 10 Preparation of 2-chloro-4,5-diiodoimidazole 2-Chloroimidazole (5.13 g) was suspended in water (150 ml), and an aqueous solution of 6N sodium hydroxide (17 ml) was added. Next, iodine (25.9 g) was added and was stirred at a room temperature for 3 hours. After that, the reaction mixture was treated with an aqueous solution of sodium sulfite, the deposited matters were collected by filtration and dried, there was obtained 2-chloro-4,5-diiodoimidazole (16.4 g, yield: 92.5%) as yellow solid. 1H-NMR (DMSO-d6) delta(ppm): 13.61 (1H, bs) 13C-NMR (DMSO-d6) delta (ppm): 133.07.

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; Otsuka Pharmaceutical Company, Limited; EP1553088; (2005); 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. 78597-27-0, name is 6-Iodo-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Iodo-1H-benzo[d]imidazole

Preparation 23 Preparation of a Mixture OF 6-IODO-1- [3- (TETRAHYDRO-PYRAN-2-YLOXY)-PROPYL]-LH- benzoimidazole and 5-IODO-1- [3- (TETRAHYDRO-PYRAN-2-YLOXY)-PROPYL]-LH- benzoimidazole Stir 5-IODO-LH-BENZOIMIDAZOLE (U. S. S. R. pat. 1616911,30 Dec. 1990; 2.0 g, 8.2 mmol), 2- (2-bromoethoxy) tetrahydro-2H-pyran (4.0 mL, 26.5 mmol), sodium hydride (0.78 g, 32.8 mmol) in DMF (20 mL) at room temperature for 2 h. Extract the product with 3: 1 CHLOROFORM/ISOPROPYL alcohol and wash with saturated sodium chloride. Dry the organic phase over sodium sulfate and filter to give a dark yellow oil. Purify by silica gel flash chromatography eluting with dichloromethane to 10% THF/90% dichloromethane to afford a light yellow oil as a mixture of the two titled compounds (2.59 g, 83%). MS (electrospray, m/z) 387.1 (M+1).

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; ELI LILLY AND COMPANY; WO2004/50659; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 930-62-1, The chemical industry reduces the impact on the environment during synthesis 930-62-1, name is 2,4-Dimethylimidazole, I believe this compound will play a more active role in future production and life.

Compound 5.5. 5-Iodo-2,4-dimethyl-lH-imidazole. NIS (14.0g, 62.4mmol) was added portion-wise to a solution of 2,4-dimethyl- lH-imidazole (5.00 g, 52.0 mmol) in acetonitrile (100 mL). The mixture was heated at 80 C for 16 hours, then cooled to room temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (300 mL) and water (80 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgS04) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc 1 : 1 to 10% MeOH in EtOAc) to yield the title compound as a light yellow solid (8.56 g, 74%). m/z (ES+) 223(M+H)+. NMR (400 MHz, CDC13) delta 9.69 (br s, 1H), 2.38 (s, 3H), 2.19 (s, 3H)

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, 2,4-Dimethylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 870837-18-6, 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. 870837-18-6 name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

Aqueous hydrogen peroxide (30%, 18.9 mL) was added drop-wise over 20 minutes to a solution of 3-methoxy-4-(4-methyl-1/-/-imidazol-1-yl)benzaldehyde (5.0 g, 20.0 mmol) and potassium hydroxide (6.1 g, 92.5 mmol) in MeOH (38 mL) and water (6.6 mL) at 65 C. Following completion of the addition the reaction was stirred at room temperature for an additional 25 minutes. The reaction was then allowed to cool to room temperature and was acidified with cone. HCI. The resulting precipitate was filtered to provide the title compound as a white solid. Yield: 4.6 g, 17.1 mmol, 74%. MS (APCI) m/z 232.9 (M+1 ). 1H NMR (400 MHz, CD3OD) 2.45 (br s, 3H), 4.00 (s, 3H), 7.65 (br s, 1 H), 7.67 (d, J=8.4 Hz, 1 H), 7.82 (dd, J=8.3, 1.6 Hz, 1 H), 7.89 (d, J=1.6 Hz, 1 H), 9.24 (d, J=1.6 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
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. 1219741-19-1, name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1219741-19-1

Et3N (20.95 mL, 150 mmol) and 2-(trimethylsilyl)ethoxy methyl chloride (17.29 mL, 98 mmol) were added to a solution of Intermediate IA (26.8 g, 75 mmol) in THF (200 mL). The reaction was stirred at rt for 1 h. Volatiles were removed and the residue partitioned between EtOAc and water. The organic phase was washed with 2N aqueous HCl and brine, dried (MgSO4) and concentrated to afford the title compound as a white solid. LC-MS: calculated for C14H20ClIN2O3SSi 485.97, observed m/e 428.83 (M + H)+(Rt 2.30 min).

The synthetic route of 1219741-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; BOOKSER, Brett, C.; DANG, Qun; GIBSON, Tony, S.; JIANG, Hongjian; CHUNG, De Michael; BAO, Jianming; JIANG, Jinlong; KASSICK, Andy; KEKEC, Ahmet; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F., Anthony; SEBHAT, Iyassu; WILSON, David; WODKA, Dariusz; WO2010/47982; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-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 3012-80-4, Formula: C9H8N2O

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Compound 2 was synthesized hydrothermally by reaction of H3PW12O40 xH2O (0.075g, 0.026 mmol), AgNO3 (0.051g, 0.3 mmol), H2biim (0.008g, 0.06 mmol) and 10 mL distilled water in a 25 ml Teflon-lined autoclave. The pH was adjusted to 2 with 1.0 mol L-1 HNO3. The mixture was heated under autogenous pressure at 160 C for 5 days and then was left to cool to room temperature. Red crystals could be isolated in about 60% yield and dried at room temperature for the further characterization. Anal.Calcd for 2: C7.13,H0.50, N6.23. Found: C7.02,H0.45,N6.42%. IR(ITR mode,cm1): 1502(s),1412(w),1352(s),1243(w),1153(s),1075(s),968(s),890(s),793(s).The IR spectrum of compound 2 is shown in the Supporting information (Fig. S6).

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,1’H-2,2′-Biimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lu, Xin-Xin; Luo, Yu-Hui; Lu, Chen; Chen, Xin; Zhang, Hong; Journal of Solid State Chemistry; vol. 232; (2015); p. 123 – 130;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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: A vessel with a magnetic stirrer bar was charged with imidazole derivative (0.5 mmol), CuI (10 mg, 0.05 mmol), Cs2CO3 (0.33 g, 1 mmol), PPh3 (26 mg, 0.1 mmol) and tetrabutylammonium bromide (TBAB) (0.2 g, 0.6 mmol) under a nitrogen atmosphere. The reaction vessel was evacuated and backfilled with nitrogen three times. In a separate flask, a solution of dry dioxane (2 mL) containing the 1,1-dihalo-1-alkenes (1 mmol) was evacuated and back-filled with nitrogen gas three times. The dioxane solution was then added to the reaction flask via a syringe and the reaction mixture heated to 100 C for 30 hours. The reaction mixture was cooled to room temperature, quenched with 5 mL of a saturated NH4Cl solution, and extracted with ethyl acetate (3 x 10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as the eluent to afford the corresponding products:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Propylimidazole, its application will become more common.

Reference:
Article; Wang, Man-Gang; Yu, Hua; Wu, Jun; Shang, Zhi-Cai; Journal of Chemical Research; vol. 37; 9; (2013); p. 570 – 573;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem