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. 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 1H-Benzo[d]imidazol-2-amine

General procedure: A mixture of aromatic aldehyde 1 (1.0 mmol), dimedone 2 (1.0 mmol), 2-aminobenzimidazole 3 (1.0 mmol) and [DABCO](HSO3)2(Cl)2 (0.2 mmol, method A) or [DABCO](SO3H)2(HSO4)2 (0.02 mmol, method B) was stirred at 100 C for the appropriate time. The progress of the reaction was followed by TLC (n-hexane/ethyl acetate-8:2). After completion, the obtained solid mixture was washed with cooled water (2 ¡Á 2 mL) to separate the catalyst. Then, warm ethanol (3 mL) was added to the reaction media, and the solid product was filtered and dried in air.

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; Seyyedi, Narges; Shirini, Farhad; Langarudi, Mohaddeseh Safarpoor Nikoo; Jashnani, Setareh; Journal of the Iranian Chemical Society; vol. 14; 9; (2017); p. 1859 – 1867;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 705-09-9, These common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, 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 solution of 14a (300mg, 1.8mmol, leq) in DMF(4mL) was added NaH(60%, 75mg, 1.8mmol, leq) at 0~5C. The resulting mixture was stirred for 30min at 0~5C and to the mixture was added 68b(459mg, l.deltammol, leq) portion- wise. The reaction mixture was stirred at r.t. over a weekend. The solvent was removed and the residue was purified by column chromatography (PE:EA=4: 1) to give 68c (33Omg, yield: 50%) as a colorless oil. ES-MS m/z: 377 (M++l)

Statistics shows that 2-(Difluoromethyl)-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 705-09-9.

Reference:
Patent; XCOVERY, INC.; LIANG, Congxin; LI, Zhi-Gang; WO2010/5558; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, 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. Safety of Dimethyl 4,5-imidazoledicarboxylate

1H-Imidazole-4,5-dicarboxylic acid dimethyl ester (2 g, 10.87 mmol, 1 equiv. ) was dissolved in THF (55 mL, 0.2 M) and DMAP (1.46 g, 11.95 mmol, 1.1 equiv. ) before Di- tert-butyl dicarbonate (3.50 g, 16.29 mmol, 1.4 equiv. ) was added. The reaction was stirred for 16 hours before being quenched with saturated NH4Cl (30 mL) and extracted with ethyl acetate (2 x 30 mL) and the organic layer washed several times with water (4 x 30 mL), brine solution (50 mL). It was dried over Na2SO4, filtered and concentrated in vacuo. Imidazole-1,4,5-tricarboxylic acid 1-tert-butyl ester 4,5-dimethyl ester 252 (3.85 g, 100%, 10.87 mmol). 1H NMR (300 MHz) CDCl3 delta 8.02 (s, 1 H), 3.99 (s, 3 H), 3.92 (s, 3 H). MS: 306.8 (M+23). TLC Rf: 0.6 Hexanes/Ethyl acetate (1/1)

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; WO2004/35576; (2004); A2;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Computed Properties of C22H17IN2

Compound 1 (2.2 g, 5.0mmol), o-formylphenylboronic acid(1.2 g, 7.5mmol), K3PO4 (3.2 g, 15mmol), Pd (PPh3)4 (0.6 g, 1.0mmol) is dissolved in DMF/H20 (30mL/6mL). The system is replaced with nitrogen and warmed at 90C, the reaction is stirred overnight. The reaction solution is diluted with ethyl acetate (50mL), wash with saturated brine (25mL X 3), dry over anhydrous sodium sulfate, and dry under reduced pressure. Crude column chromatography (PE: EA = 5:1), and then obtained brown solid compound 2 (810 mg, 39%).

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; Lunan Pharmaceutical Group Co., Ltd.; Zhang Guimin; Guan Yongxia; Li Xin; (15 pag.)CN107556315; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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: Ethyl 2-chloro-2-oxoacetate (8.19 g, 60.0 mmol) was added dropwise over 20 min to the corresponding imidazole (60.0 mmol) in CH2Cl2 (500 mL) at -20 C. Then, DIPEA (7.75 g, 10.5 mL, 60.0 mmol) was added at -20 C, the mixture was warmed up to rt and stirred for 12 h. The resulting mixture was washed with H2O (3 ¡Á 150 mL), the organic layer was dried over Na2SO4 and evaporated in vacuo [50]. 4.2.1 Ethyl 2-(5-bromo-1-methyl-1H-imidazol-2-yl)-2-oxoacetate (10h) (0013) Yield 15.0 g (96%); yellowish oil. 1H NMR (500 MHz, CDCl3) delta 7.32 (s, 1 H), 4.46 (q, J =7.1 Hz, 2 H), 4.02 (s, 3 H), 1.41 (t, J =7.1 Hz, 3 H). 13C NMR (126 MHz, CDCl3) delta 176.5, 163.2, 140.9, 132.6, 114.8, 62.6, 33.9, 14.0. LC/MS (CI): m/z = 261/263 [M+H]+. Anal. Calcd. for C8H9BrN2O3: C 36.80; H 3.47; N 10.73; Br 30.61. Found: C 36.66; H 3.65; N 10.58; Br 30.53.

The synthetic route of 1003-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Geraschenko, Oleksandr V.; Solomin, Vitalii V.; Vashchenko, Bohdan V.; Khodakivskyi, Pavlo; Tolmachev, Andrey A.; Grygorenko, Oleksandr O.; Journal of Fluorine Chemistry; vol. 229; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, name is 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. Safety of 1H-Imidazole

Synthesis of 1-benzylimidazole 9 illustrated by step (a) of FIG. 3. (0085) According to the selected experimental protocol, 44 g of imidazole (0.65 mol.), 100 g of benzyl chloride (0.78 mol.), and 60 g of KOH (1.07 mol.) in 700 ml of THF are placed in a 1-liter balloon flask. The reaction mixture is brought to reflux for 120 h, then cooled at ambient temperature. The organic phase is filtered and the solvent is evaporated under reduced pressure. The obtained solid product is dissolved in 500 ml of CH2Cl2, then washed with water (3¡Á100 ml). The organic phase is dried on Na2SO4, filtered, then evaporated under reduced pressure. The collected solid is recristallized in toluene to yield 67 g of desired product.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peugeot Citroen Automobiles SA; CNRS (Centre National de la Recherche Scientifique); Glipa, Xavier; Ameduri, Bruno; Delon, Louis; Jones, Deborah; Roziere, Jacques; Frutsaert, Guillaume; US8859160; (2014); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

t-BuLi (0.188 ml_, 0.32 mmol, 1.7 M) was added dropwise to a solution of compound D6 ((S), R6 = H, R7 = Ph; 46 mg, 0.21 mmol) in THF (1.5 ml_) at -78 0C. The mixture was stirred for 45 minutes before compound D7 (R10 = 3-MeO- Phenyl, R9 = 4-(4-methylimidazol-1-yl)) was added in THF (1.0 ml_) in fast drops. The resulting mixture was stirred for 2 hours before it was diluted with EtOAc (50 ml_) and NH4CI solution (10 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated to give the crude product which was purified by column chromatography eluting with EtOAc/hexanes to yield compound D8 ((S), R6 = H, R7 = Ph; R10 = 3-MeO-Phenyl, R9 = 4-(4-methylimidazol-1 -yl)).

The synthetic route of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/153793; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15469-97-3, 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. 15469-97-3 name is 1-Trityl-1H-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.

(i) (2R)-1-(benzyloxy)-3-(1-trityl-1H-imidazol-2-yl)-2-propanol In an argon atmosphere, n-butyllithium (1.6 M solution in hexane, 6.9 ml) was added drop by drop to a solution of 1-tritylimidazole (3.10 g) in THF (80 ml) under ice cooling. After stirring at the same temperature for 30 minutes, (R)-2-[(benzyloxy)methyl]oxirane (1.52 ml) was added. After stirring under ice cooling for 1.5 hours and at room temperature for 1 hour, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and saline and dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane 1:1) to yield the titled compound (1.402 g) as a pale-yellow oily substance. 1H-NMR (CDCl3) delta: 2.06 (2H, dd, J=2.8 Hz, 18.0 Hz) 3.08 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.21 (1H, dd, J=5.4 Hz, 9.8 Hz), 3.55-3.7 (1H, m), 4.36 (2H, s), 6.73 (1H, d, J=1.4 Hz), 6.93 (1H, d, J=1.4 Hz), 7.0-7.4 (20H, m).

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

Reference:
Patent; Tasaka, Akihiro; Hitaka, Takenori; Matsutani, Etsuya; US2002/173526; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 939-70-8, 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 939-70-8 as follows.

General procedure: To the solution of 2-acetyl benzimidazole 1 (0.01 mol) in MeOH (20 mL) was added 10% aqueous NaOH (2 mL) at 0C with stirring. Then, the solution of aromatic aldehydes (0.01 mol) in MeOH was added drop-wise. The reaction mixture was magnetically stirred for 12 h. After completion of the reaction (monitored by TLC) the reaction mixture was poured over crushed ice. The separated solid was filtered, washed with water and dried. The residue was purified by column chromatography (silica gel with 10% ethyl acetate in petroleum ether) to afford pure benzimidazole derived chalcone 2a-m.

According to the analysis of related databases, 939-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meshram, Gangadhar A; Vala, Vipul A.; Wagh, Pramod A.; Deshpande, Shruti S.; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 5; (2016); p. 613 – 623;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-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 693-98-1, Quality Control of 2-Methyl-1H-imidazole

10 mmol of 2-methyl-1H-imidazole was added to a suspensionof potassium carbonate (10 mmol) in acetonitrile (10 mL), and then stirred for 15 min at r.t. 10 mmol of1-(chloromethyl)benzene was added to the reaction mixture and the mixture was heated to 70C and kept for 72 h. After completion of the reaction, the solvent was removed and the residue was dissolved in EtOAc (20 mL), washed with H2O(2¡Á10 mL) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: CHCl3)to afford the desired product. Yield 38%; yellow oil; UV-Vis (chloroform, lambda, nm): 290; IR spectrum (KBr, nu, cm-1): 2939,1712, 1508, 1434, 1365, 1272, 1118, 983, 721; 1H NMR (250.13 MHz, CDCl3) delta: 7.43-7.32 (m, 5H), 7.17-7.14 (m, 2H), 6.99(d, J = 1.3 Hz, 1H), 6.84 (d, J = 1.2 Hz, 1H), 5.11 (s, 2H), 2.27 (s, 3H); 13C NMR (62.9 MHz, CDCl3) delta: 144.3, 138.0, 129.3,128.1, 127.5, 127.1, 120.9, 49.2, 13.4.

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; Bouchouit; Bouraiou; Bouacida; Belfaitah; Merazig; Journal of Structural Chemistry; vol. 57; 4; (2016); p. 835 – 839; Zh. Strukt. Kim.; vol. 57; 4; (2016); p. 873 – 876,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem