Category: imidazoles-derivatives

68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, 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. COA of Formula: C10H8N2O

To a solution of 2-phenyl-1H-imidazole-4-carbaldehyde (0.35 g) in dimethylformamide (5 mL) were added potassium carbonate (843 mg) and 1-(bromomethyl)-4-fluorobenzene (462 mg) and the mixture was stirred at 75C for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in a mixture of 40% methylamine-methanol solution (474 mg) and methanol (5 mL), and the mixture was stirred for 5 min. Sodium borohydride (154 mg) was added and the mixture was stirred for 1 hr. Saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0?4:1) and dissolved in methanol. A 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from a mixed solution of methanol-tetrahydrofuran (1:4) to give the title compound as colorless crystals (yield 450 mg, yield 60%). melting point: 169-171C. 1H-NMR(DMSO-d6)delta:2.59(3H,t,J=5.1Hz), 4.25(2H,t,J=4.9Hz), 5.49(2H,s), 7.13-7.30(4H,m), 7.53-7.68(3H,m), 7.70-7.76(2H,m), 7.83(1H,s), 9.72(2H,brs), 1H not detected.

The synthetic route of 68282-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2196459; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 614-97-1, 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. 614-97-1 name is 5-Methyl-1H-benzo[d]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.

General procedure: ethyl 5-(bromomethyl)-1,3-diphenyl-1H-pyrazole-4-carboxylate (5, 0.38 g, 1.00 mmol) is taken in THF (20 ml) and stirred at room temperature for 10 min. 1H-benzo[d]imidazole-2-thiol (8a, 0.15 g, 1.00 mmol) was added followed by the potassium hydroxide (0.06 g, 1.00 mmol) and tetrabutyl ammonium bromide (TBAB) (0.03 g, 0.10 mmol). The above reaction mass is stirred at room temperature for about 4-6 hours. After the completion of the reaction (monitored by TLC), the reaction mixture was concentrated under reduced pressure to evaporate THF and later extracted with diethyl ether (3 x 20 ml), washed with water (3 x 20 ml). The organic extract was dried with anhydrous sodium sulfate, concentrated under reduced pressure and crystallized to provide the desired compound (9a) in 64% yield (0.29 g). This is then recrystallized from saturated solution of methanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methyl-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Article; Doddaramappa, Shridevi D.; Lokanatha Rai; Srikantamurthy, Ningaiah; Chandra; Chethan, Javarasetty; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3671 – 3675;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 144689-93-0, name: Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

EXAMPLE 2; 3-(4-Bromo-benzyl)-5-(1-hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazol-4-carboxylic acid ethyl ester (IV; XBr)A mixture of a compound of formula (IX), in which R4 is ethyl (100 g, 0.417 mol), a compound of formula (X), in which X=Z=Br (107.5 g, 1.03 mol) and K2CO3 (71 g, 0.516 mol) in DMA (400 mL) is reacted at room temperature, under stirring, for 18 hours. The reaction mixture is then diluted with water and the precipitated solid is filtered and dried in a static dryer under vacuum.152 g of the title compound are obtained; yield: 89%.

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; DIPHARMA FRANCIS S.R.L.; US2008/76932; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 14741-71-0, The chemical industry reduces the impact on the environment during synthesis 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, I believe this compound will play a more active role in future production and life.

[0295] To a suspension of SMI (25.9 g, 148 mmol) and SM2 (30 g, 147 mmol) in ethanol (400 mL) was added SM3 (33.5 g, 394 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was heated to reflux for 6 h. The mixture was then cooled to 20 C and the precipitate collected by filtration to give Ethyl 2-(4-methyl-[l,4]diazepan-l-yl)-l,7,l lb- triazabenzo[c]fluorene-6-carboxylic acid (40 g, 68 yield) as a pale yellow solid. LCMS

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, Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HADDACH, Mustapha; WO2015/172123; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 24134-09-6, 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

n-BuLi (1.23 M in hexanes, 18.9 mL, 23.2 mmol) was added dropwise to a stirred slurry of 5-bromo-1,2-dimethyl-1H-imidazole (5.13 g, 27.8 mmol) in THF (40 mL) at -78 C. under nitrogen. After stirring for 20 minutes, the slurry was treated dropwise over 2 minutes with a solution of methyl 3-(benzyloxy)-4-chloro-2-methoxyquinoline-6-carboxylate (3.32 g, 9.28 mmol, Intermediate 32) in THF (20 mL). The flask was then rinsed with THF (10 mL), and that was added to the imidazole flask. The reaction was stirred in the dry ice/acetone bath for 10 minutes, then removed from the cold bath and stirred for 20 minutes, then stirred in an ice bath for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl and concentrated to remove the THF. The aqueous residue was partitioned between water (300 mL) and DCM (250 mL). The layers were separated and the aqueous layer further extracted with DCM (250 mL). The organics were combined, dried (Na2SO4), filtered and concentrated to dryness to provide an orange oil. The crude material was purified by FCC (0-10% MeOH/DCM) to afford the title compound as a yellow solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.13 (s, 1H), 7.70 (d, J=8.7 Hz, 1H), 7.58-7.55 (m, 2H), 7.42-7.34 (m, 4H), 6.20 (s, 2H), 5.20 (s, 2H), 4.62 (s, 1H), 4.16 (s, 3H), 3.42 (s, 6H), 2.32 (s, 6H). MS (ESI): mass calcd. for C28H28ClN5O3, 517.2. m/z found, 518.1 [M+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, 5-Bromo-1,2-dimethyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); 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. 54624-57-6, name is 2-Bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: imidazoles-derivatives

2-bromo-1 H-benzo[d]imidazole (177 mg, 0.9 mmol), bispinacolato diboron (250 mg, 0.99 mmol) and KOAc (265 mg, 2.7 mmol) were dissolved in dioxane (9 ml). After purging with N2, Pd(dppf)CI2 (37 mg, 0.045 mmol) was added. After stirring overnight at reflux temperature the reaction was cooled to room temperature the reaction mixture was diluted with some ethyl acetate (20 ml). The mixture was filtrated through a pad of celite and the solvent was evaporated under reduced pressure to give 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H- benzofdlimidazole as a black oil. The crude product was used in the next step without further purification

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSD OSS B.V.; HUISMAN, Ines; VAN DER STELT, Marcelis; WIEDENHOF, Wouter; BAKER-GLENN, Charles, Anthony, Graham; BLACKABY, Wesley, Peter; TRIVEDI, Naimisha; WO2013/41457; (2013); 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., Product Details of 60-56-0

General procedure: To a solution containing a thione (1, 6, 8, or 10, 1.0 equiv) in water (2.5 mL) and acetonitrile(1.5 mL) was added saturated aqueous ammonium hydroxide. After the solution was stirred atroom temperature for 30 min, a 3-(chloromethyl)coumarin (2, 1.5 equiv) was added and stirring wascontinued at room temperature for 15 min to 2.0 h. Acetonitrile therein was removed under reducedpressure and water was further removed under reduced pressure over P2O5 with a Kuegelrohr GKR-51apparatus (BUCHI, Flawil, Switzerland). The residue was purified by use of column chromatographypacked with silica gel to give the desired products with purity of >98.0%, as determined by HPLC(see Supplementary Materials).

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsay, Shwu-Chen; Lin, Shu-Yu; Huang, Wen-Chieh; Hsu, Ming-Hua; Hwang, Kuo Chu; Lin, Chun-Cheng; Horng, Jia-Cherng; Chen, I-Chia; Hwu, Jih Ru; Shieh, Fa-Kuen; Leyssen, Pieter; Neyts, Johan; Molecules; vol. 21; 2; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 5465-29-2, name is 2-Propylbenzimidazole, molecular formula is C10H12N2, 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. Recommanded Product: 2-Propylbenzimidazole

General procedure: A solution of 10.0 mmol of compound 1a-1d in 14 mL of concentrated sulfuric acid was heated to 100-105C, 14 mL (0.26 mol) of 30% aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5465-29-2, its application will become more common.

Reference:
Article; Brusina; Nikolaev; Ramsh; Piotrovskii; Russian Journal of Organic Chemistry; vol. 52; 10; (2016); p. 1528 – 1530; Zh. Org. Khim.; vol. 52; 10; (2016); p. 1533 – 1535,3;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 56248-10-3, name is 5-Phenyl-1H-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 56248-10-3, category: imidazoles-derivatives

In a closed vessel a slurry of 4-phenyl-1H-imidazole-2-carbaldehyde (200 mg, 1.16 mmol) and sodium carbonate (60 mg, 0.6 mmol) in ethanol (4 mL) was treated with propylene oxide (170 muL, 2.4 mmol) and heated at 100 C. for 3 h. The cooled solution was filtered and the solids washed with DCM. The volatiles were removed in vacuo to yield the crude title compound which was used without further purification (250 mg, 63%). LC-MS: m/z=231.5 (MH+), tR=0.41 min, method A

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, 5-Phenyl-1H-imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; US2010/16303; (2010); 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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 71759-89-2

Intermediate 4.1 : (5-chloro-2-nitro-phenyl)-(lH-imidazol-4-yl) methanol To a solution of 4-iodo-lH-imidazole (2 g, 10.3 mmol) in THF (20 mL) was added dropwise isopropylmagnesiumchloride (2 M in THF, 12 mL, 23.7 mmol) at room temperature. The reaction solution was stirred at rt for 2 h. To this solution was added 5-chloro-2-nitro-benzaldehyde (2.9 g, 15.5 mmol) in 10 mL THF. The solution was stirred at room temperature for 2 h. The reaction was quenched with aqueous NH4CI solution. The mixture was extracted twice with EA. The combined organic phases were dried and concentrated in vacuo. The residue was purified silica gel chromatography column (PE/EA, 3/1 to 1/1) to give the title compound as a brown solid

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; LEO PHARMA A/S; SOERENSEN, Morten Dahl; LARSEN, Jens Christian Hoejland; NOERREMARK, Bjarne; LIANG, Xifu; HUANG, Guoxiang; WO2013/82751; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem