Category: imidazoles-derivatives

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. 51-17-2, name is 1H-Benzo[d]imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Benzo[d]imidazole

STEP A: 1-methyl-benzimidazole 14.1 g of methyl iodide and 6.15 g of potassium hydroxide were added to a suspension of 11.8 g of benzimidazole in 50 ml of ethanol and 30 ml of water and the mixture was refluxed for 6 hours and was then cooled. The mixture was extracted three times with chloroform and the combined chloroform extracts were dried and filtered. The filtrate was evaporated to dryness and the oily residue was chromatographed over neutral alumina. Elution with chloroform yielded 1-methyl-benzimidazole as a crude oil which was used as is for the next step.

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; Roussel Uclaf; US4151280; (1979); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 570-22-9, name: 1H-Imidazole-4,5-dicarboxylic acid

General procedure: Ethane-1,2-diamine (4a; 60mg; 1mmol) and iminodiacetic acid (5; 266mg; 2mmol) were mixed thoroughly, grinded and subjected to focused microwave irradiation at 135 C for 4 minutes. TLC of reaction mixture over silica gel G using ethyl acetate: MeOH (7:3) as mobile phase showed that the reaction is complete. Crude product, so obtained was purified by crystallization from methanol: water (9.5:0.5) to give pure product 9a. Yield: 83%.

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; Kumar, Anuj; Banerjee, Somesh; Roy, Partha; Sondhi; Sharma, Anuj; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 501 – 504;,
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. 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C11H12N2

General procedure: 2.3. Typical procedure for the synthesis of imidazolium ion tethered TsDPENs 5a. A solution mixture of the intermediate 3 (818 mg, 1.5 mmol) and 1,2-dimethyl-1H-imidazole (173 mg, 1.8 mmol) in acetonitrile (2 mL) was heated at 70 C for 30 h. The solvent was removed under reduced pressure, and the residue was washed with a mixture solvent (hexane/ethyl acetate = 10:1) and dried in vacuo to give an intermediate 4a, to which HCl solution (3 mL, 4 M in dioxane) was added. The reaction mixture was stirred at room temperature for 5 h and the precipitation was filtered and washed with hexane to give the Boc deprotected intermediate, which was used for the next step directly without further characterization. The Boc-deprotected intermediate was subsequently neutralized by Na2CO3 (159 mg, 1.5 mmol) in MeOH (2 mL). The mixture was stirred for 5 h and the solvent was removed to dryness. The solid residue was dissolved in dry CH2Cl2 and filtered, and concentrated to give the product 5a as a white solid (550 mg, 68% yield for 2 steps).

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; Kang, Guowei; Lin, Silong; Shiwakoti, Atul; Ni, Bukuo; Catalysis Communications; vol. 57; (2014); p. 111 – 114;,
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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5BrN2

5-Bromo-1-methyl-1H-imidazole (6.66 g, 41.4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2 atmosphere. The contents were cooled to 0 C. in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C. and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 15: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C., then slowly warmed to room temperature, then heated to 40 C. in an oil bath and heated with stirring at that temperature for approximately 36 hours. The contents were then cooled to 0 C., quenched with a saturated aqueous NH4Cl solution, diluted with ethyl acetate and transferred to a reparatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgSO4, filtered, then distilled under reduced pressure to afford an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM/(10% of a 2 M NH3 MeOH in DCM)) to provide the title compound.

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; Janssen Pharmaceutica NV; 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.; US2015/105404; (2015); A1;,
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 53710-78-4 as follows. Product Details of 53710-78-4

General procedure: 60% NaH (0.23 mmol) was added to a solution of 6a (0.23 mmol) in dry DMF (15 mL) at 0-5C. After stirring for 15 min at room temperature. 1-(3-chloropropyl)-1H-imidazole or 1-(4-chlorobutyl)-1H-imidazole (0.34 mmol) was added and stirred for 12 h at 60-65 C. After cooling, the mixture was poured into H2O (120 mL) and the resulting solution was extracted with ethyl acetate (60 mL × 3). The organic phase was combined, washed with brine (180 mL× 3), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate/MeOH (5:10:1, v/v) as eluent to afford 7d or 7e.

According to the analysis of related databases, 53710-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Yuanyuan; Ruan, Wenchen; Gao, Anhui; Zhou, Yubo; Gao, Lixin; Xu, Meng; Gao, Jianrong; Ye, Qing; Li, Jia; Pang, Tao; Pharmazie; vol. 72; 12; (2017); p. 707 – 713;,
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. 693-98-1, name is 2-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Methyl-1H-imidazole

General procedure: Compounds 1-18 were synthesized using the following generalprocedure reported by Salvio et al. [41]. A mixture of potassium carbonate(2.0 g, 14.4 mmol), imidazole derivatives 27-28 (32.9 mmol)and compounds 29-37 (4.7 mmol) in dry acetonitrile (50 ml) was heatedunder reflux and the progress of the reaction was monitored byTLC. Then the solvent was evaporated under the vacuum and the residuewas dissolved in DCM (100 ml) *. The organic layer was washedwith saturated sodium bicarbonate aqueous solution (2×50 ml),passed through diatomaceous earth, dried over sodium sulfate, evaporatedunder the vacuum, and purified by flash column chromatography(ethyl acetate-hexane 0-100%)** to give the products 1-18.*Note 1: Ethyl acetate (200 ml) was used for compounds 17 and 18.**Note 2: Compounds 17 and 18 (ethyl acetate-methanol 0-100%).

The synthetic route of 693-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khalili Arjomandi, Omid; Kavoosi, Mahboubeh; Adibi, Hadi; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 2a (0.50 g, 1.48 mmol), propyl triphenylphosphonium bromide (0.63 g, 1.63 mmol) and NaH (powered 95%, 0.05 g, 2.22 mmol) in anhydrous THF (8 mL), was stirred at rt for 8 h under Ar atmosphere. Then, the reaction mixture was quenched with saturated aqueous NaHCO3 (5 mL) solution and extracted with CH2Cl2 (3 × 15 mL). The organic layer was washed with H2O (1 × 10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, EtOAc/Hex 1:1) to furnish the Z-3 isomer (0.44 g) which is the sole isolated product. Yield: 81%; Rf 0.63 (EtOAc/Hex 4:1); tR 12.42 min (30% MeCN ? 100% MeCN in 30 min); ESI-MS (m/z): 123.18 [M + H], 243.26 [Tr]; 1H NMR (400 MHz, CDCl3): delta 7.64 (br s, 1H), 7.36-7.35 (m, 9H), 7.16-7.13 (m, 6H), 6.75 (br s, 1H), 6.25 (dt, 1H, J = 1.5, 11.6 Hz), 5.60 (dt, 1H, J = 7.5, 11.6 Hz), 2.28 (quint d, 2H, J = 1.7, 7.5 Hz), 1.00 (t, 3H, J = 7.5 Hz); 13C NMR (160 MHz, CDCl3): delta 141.70, 137.64, 137.15, 134.53, 129.66, 128.29, 128.18, 120.20, 119.00, 76.03, 22.55, 13.79.

The synthetic route of 1-Trityl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agelis, George; Resvani, Amalia; Koukoulitsa, Catherine; Tumova, Tereza; Slaninova, Jirina; Kalavrizioti, Dimitra; Spyridaki, Katerina; Afantitis, Antreas; Melagraki, Georgia; Siafaka, Athanasia; Gkini, Eleni; Megariotis, Grigorios; Grdadolnik, Simona Golic; Papadopoulos, Manthos G.; Vlahakos, Demetrios; Maragoudakis, Michael; Liapakis, George; Mavromoustakos, Thomas; Matsoukas, John; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 352 – 370;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113775-47-6, name is Dexmedetomidine, 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 113775-47-6, name: Dexmedetomidine

A mixture of (+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1H-imidazole (dexmeditomidine; 2.00 g, 10.0 mmol) prepared as described in Cordi et al., Synth. Comm. 26: 1585 (1996), in THF (45 mL) and water (40 mL) was treated with NaHCO3 (8.4 g, 100 mmol) and phenylchlorothionoformate (3.7 mL, 27.4 mmol). After stirring for four hours at room temperature, the mixture was diluted with water (30 mL) and ether (75 mL). The organic layer was removed, and the aqueous layer extracted twice with a 50 ml volume of ether. The organic layers were dried over MgSO4 and filtered. The residue was concentrated under vacuum, diluted with MeOH (54 mL) and reacted with NEt3 (6.5 mL) at room temperature for 16 hours. The solvent was removed under vacuum and replaced with 30% CH2C12:hexane. The solvent was removed again and solids formed. After further resuspension in 30% CH2C12:hexane, the solid was collected on a filter, washed with CH2C12:hexane and dried under vacuum to give Compound 1 ((+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1,3-dihydro-imidazole-2-thione) 1.23 g (53%). A schematic of the preparation of Compound 1 is shown above. Characterization of the product yielded the following. Optical rotation: [a]D20+14 (c 1.25 in MeOH). 1H NMR: (300 MHz, DMSO) d 11.8 (s, 1H), 11.6 (s, 1H), 7.03-7.01 (m, 2H), 6.95-6.91 (m, 1H), 6.50 (s, 1H), 4.15 (q, J=6.9 Hz, 1H), 2.25 (s, 3H), 2.20 (s, 3H), 1.38 (d, J=6.9 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dexmedetomidine, and friends who are interested can also refer to it.

Reference:
Patent; Allergan, Inc.; US2005/59721; (2005); A1;,
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 253453-91-7 as follows. Recommanded Product: 2-Chloro-1-methyl-1H-imidazole

Step C: (2-Chloro-3-methyl-3H-imidazol-4-yl)-(4-chloro-phenyl)-methanone. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added 2-chloro-1-methyl-1H-imidazole (15 g, 0.128 mol) and THF (250 mL). The reaction mixture was cooled to -78 C. and n-BuLi (2.5 M in hexanes, 54 mL, 0.135 mol) was added. The pale yellow suspension that formed was stirred for 1 h and a solution of 4-chloro-N-methoxy-N-methyl-benzamide (27 g, 0.135 mol) in THF (50 mL) was then added dropwise. After the addition was complete, the cooling bath was removed and the reaction was allowed to warm to rt. The reaction mixture was quenched with satd. aq. NH4Cl (150 mL), transferred to a separatory funnel, and extracted with EtOAc (1.5 L). The organic layer was washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure to yield the product as a crystalline solid. Recrystallization from EtOAc-hexanes afforded the desired ketone (31.2 g, 97%) as a white crystalline solid. mp 173-174 C. IR (film): 1639, 1589, 1517, 1395, 1377, 1253, 1186, 902, 841, 756, 738, 695, 676 cm-1. 1H NMR (400 MHz, CDCl3): delta7.78 (d, J=8.6 Hz, 2H), 7.44 (s, 1H), 7.44 (d, J=8.6 Hz, 2H), 3.97 (s, 3H). 13C NMR (100 MHz, CDCl3): delta183.3, 140.3, 139.5, 139.2, 136.3, 131.2, 130.4, 128.9, 33.5. HRMS (EI): m/z calcd for C11H9Cl2N2O [M+H]+, 255.0092; found, 255.0104. Anal. Calcd for C11H8Cl2N2O: C, 51.8; H, 3.06; N, 10.93. Found: C, 52.08; H, 3.16; N, 10.90. .This step is alternatively performed using 4-chlorobenzoyl chloride-in place of 4-chloro-N-methoxy-N-methyl-benzamide

According to the analysis of related databases, 253453-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Example 2 3-(5-Methyl-3H-imidazol-4-ylmethylene)-4-pyridin-4-yl-1,3-dihydroindol-2-one A mixture of 4-pyridin-4-yl-1,3-dihydroindol-2-one (50 mg, 0.24 mmol), 5-methyl-3H-imidazole-4-carbaldehyde (24.4 mg, 0.24 mmol) and piperidine (1 drop) in ethanol (2 mL) was stirred at room temperature for 2 days. The precipitate which formed was filtered. Crystals which formed in the filtrate were isolated, washed with ethanol and dried to give 7.8 mg of the title compound. 1H NMR (360 MHz, DMSO-d6) delta 13.55 (br s, 1H, NH), 11.13 (br s, 1H, NH), 8.75 (d, J=6.0 Hz, 2H), 7.85 (s, 1H), 7.50 (d, J=6.0 Hz, 2H), 7.27 (t, J=7.7 Hz, 1H), 6.97 (d, J=7.7 Hz, 1H), 6.83 (d, J=7.7 Hz, 1H), 6.76 (s, 1H, H-vinyl), 1.78 (m, 3H, CH3) MS m/z 303 [M++1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Tang, Peng Cho; Wei, Chung Chen; Huang, Ping; Cui, Jingrong; US2002/187978; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem