Month: March 2021

Electric Literature of 5465-29-2, 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 5465-29-2 as follows.

General procedure: To the reaction vessel containing benzimidazole or imidazole (1mmol), alkyl halide (1mmol), 50% NaOH (0.5mL) and anionic surfactant sodium dodecyl sulfate (5mol%) was added and the reaction mixture was vigorously stirred at room temperature or 60C. After the completion of reaction (TLC) followed by standard workup using ethyl acetate as extracting solvent the crude product was purified over silica-gel (60-120 mesh) using ethyl acetate-hexane (3:7) as eluent to afford pure products. Identities of the products were judged by the comparison of melting point, IR data, 1H NMR, 13C NMR and HRMS analyses.

According to the analysis of related databases, 5465-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chakraborty, Ankita; Debnath, Sudipto; Ghosh, Tanmoy; Maiti, Dilip K.; Majumdar, Swapan; Tetrahedron; vol. 74; 40; (2018); p. 5932 – 5941;,
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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Ethyl diethylphosphonoacetate (5.70 g) and lithium hydroxide monohydrate (1.30 g) were sequentially added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5.00 g) in THF (20 mL) and ethanol (5.0 mL), and the reaction solution was stirred at room temperature for nine hours. A 2 N sodium hydroxide solution (20 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was cooled to 0C, and 2 N hydrochloric acid (20 mL) was added to the reaction solution. The resulting precipitate was collected by filtration. The resulting precipitate was washed with water and ethyl acetate to obtain 5.10 g of the title compound. The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s, 1H), 7.60 (d, J = 16 Hz, 1H), 7.56 (s, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.16 (s, 1H), 6.66 (d, J = 16 Hz, 1H), 3.88 (s, 3H), 2.15 (s, 3H).

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; Eisai R&D Management Co., Ltd.; EP2019093; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2,Some common heterocyclic compound, 3034-50-2, name is Imidazole-4-carbaldehyde, molecular formula is C4H4N2O, 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.

(i) Preparation of 1-(triphenylmethyl)-1H-imidazol-4-carboxaldehyde (7): To a stirred suspension of 4-imidazole carboxaldehyde (from Maybridge Chemicals, United Kingdom) (35.0 g, 364 mmol) and triethylamine (55.8 mL; 400 mmol) in dichloromethane (2 L), was added a solution of triphenylmethyl chloride in dichloromethane (600 mL) while maintaining the reaction temperature at approximately 15 C. with a cooling bath. The resultant solution was warmed to room temperature and stirred for 19 h. Washed the reaction solution with a solution of saturated brine and water (1:3.5; 3*600 mL), followed by brine (1*800 mL). Dried over sodium sulfate; filtered to remove drying agent; and removed solvent under vacuum to obtain the desired tritylated product (7) as an off-white solid. MP 186.5-194 C. [Trituration of this product with ether yielded a cream-colored powder with mp 195-197 C.]

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

Reference:
Patent; Shih, Neng-Yang; Aslanian, Robert G.; Piwinski, John J.; Lupo JR., Andrew T.; Afonso, Adriano; US2002/82272; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1450-93-7,Some common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), molecular formula is C6H12N6O4S, 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.

Synthesis of (E)-4-((1H-imidazol-2-yl)diazenyl)-1-methyl-1H-pyrazol-5-amine Concentrated HCl (17.16 mL, 206 mmol) and 1H-imidazol-2-aminium sulfate (6.67 g, 25.1 mmol) were added to a 150 mL Erlenmeyer flask and cooled in ice/methanol bath to <0 C. Sodium nitrite (3.55 g, 51.48 mmol) is dissolved in ca. 20 mL of water and added dropwise to the solution above keeping the temperature below 5 C. In a separate flask sodium carbonate (27.2 g, 257 mmol) is dissolved in 200 mL of water. 1-Methyl-1H-pyrazol-5-amine (5 g, 51.48 mmol) is added. Upon cooling and stirring the solution became slushy. The 2-aminoimidazole containing solution is added to the 1-methyl-5-aminopyrazole solution, keeping the temperature below 5 C. Following complete addition the reaction mixture is kept cold and stirred for ca. 1 hour. Ethyl acetate (1 L) is added to the reaction mixture and the mixture is transferred to 2 L separatory funnel. The ethyl acetate is collected, and the aqueous phase is extracted twice more with ethyl acetate (2*1 L). The extracts were combined and evaporated providing 5.0 g of a black semi-solid. The crude (E)-4-((1H-imidizol-2-yl)diazenyl)-1-methyl-1H-pyrazol-5-amine is purified by column chromatography. The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; NOXELL COPRORATION; MURPHY, Bryan Patrick; ZHANG, Guiru; GARRETT, Garry Steven; (41 pag.)US2018/79907; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

30148-21-1, name is Ethyl 1-methyl-1H-imidazole-2-carboxylate, 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: C7H10N2O2

A solution of the methylimidazole (3.2 mL, 40.0 mmol) in 30 mL de CH3CN:Et3N (2:1) was cooled to -30 C and quickly added to a previously prepared solution of ethyl chloroformiate (7 mL, 66.0 mmol) in 10 mL of CH3CN. The mixture was stirred for 15h at rt. The solvents were removed under reduced pressure; the crude was re-dissolved in water (20 mL) and extracted with chloroform (3 ¡Á 20 mL). The organic fractions were dried and concentrated, and the resulting residue was purified by flash cromatography (aluminum oxide, 90% MeOH) to give 3.72 g of a crude ester residue which was directly used for the next step. A solution of this residue (1.5 g, 9.74 mmol) in 15 mL of aqueous NaOH (1 M) was refluxed for 1 h. The resulting mixture was acidified to pH 2.0 using HCl 10% (aprox.15 mL) and lyophilized. The crude was dissolved in MeOH and concentrated underreduced pressure to give 12 as a slighlty pink solid (1.2 g, 98%).

The synthetic route of 30148-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jimenez-Balsa, Adrian; Dodero, Veronica I.; Mascarenas, Jose L.; Tetrahedron; vol. 69; 36; (2013); p. 7847 – 7853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 78581-99-4, A common heterocyclic compound, 78581-99-4, name is 5,6-Difluorobenzimidazole, molecular formula is C7H4F2N2, 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.

CuBr 6 mg (0.04 mmol), TEMPO 5 mg (0.03 mmol), compounded in a 25 mL Schlenk reaction tube5,6-difluorobenzimidazole 62 mg (0.4 mmol),28 mg (0.2 mmol) of salicylic acid (0.2 mmol) and p-xylene (0.5 mL), followed by 33 muL of pyridine (0.4 mmol) were added and the reaction was stirred at 120C for 36 hours under reflux.Cool to room temperature, transfer all to a 25 mL flask, spin off the solvent on a rotary evaporator, add an appropriate amount of silica gel to spin dry, and then use a 300-400 mesh silica gel column. The developing solvent used is petroleum ether:ethyl acetate=16: 1 to 6:1, that is, compound III-9 26mg, yield 48%; white solid

The synthetic route of 78581-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southwest University; Cai Guixin; Xie Dan; (14 pag.)CN107955020; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2466-76-4, The chemical industry reduces the impact on the environment during synthesis 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, I believe this compound will play a more active role in future production and life.

Triethylamine (217 mg, 2.15 mmol), followed by 1-acetylimidazole (95 mg, 0.86 mmol), was added to a solution of the product from step 2 (200 mg, 0.43 mmol) in methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and water (3 mL) and treated with potassium carbonate (300 mg, 2.17 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, and dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-5percent methanol/methylene chloride provided the desired product (85 mg, 49percent) as a white foam. ESI MS m/z 407 [C2, H24F2N204 + H] + ; HPLC (Phenomenex Luna C18 (2) Column, 150 x 4.6 mm, 5R ; A: 0.05percent TFA in 95: 5 H20/CH3CN ; B: 0.05percent TFA in 5: 95 H20/CH3CN ; Gradient: 30-100percent B over 15 min; flow 1.0 mUmin ; Detection: 254 nm) 98.0percent (AUC), tR = 7.01 min. Anal. Calc’d for C21H24F2N2O4No.O. 25 H20 : C, 61.38 ; H, 6.01 ; N, 6.82 ; found: C, 61.60 ; H, 5.68 ; N, 6.59.

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-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87714; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 96797-15-8, A common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, 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.

(1S,2R) and (1R,2S)-2-(4-chlorophenyl)-1′-(1-trityl-1H-imidazol-4-yl)spiro[cyclopropane-1,3′-indolin]-2′-one 4-Iodo-1-trityl-1H-imidazole (210 mg, 0.48 mmol) was added to a suspension of racemic (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (107 mg, 0.4 mmol) in acetonitrile (2 mL) under a nitrogen atmosphere. A steady stream of nitrogen was bubbled through the suspension as it was heated to 40 C. over 15 minutes. Potassium carbonate (110 mg, 0.8 mmol), copper (I) iodide (12 mg, 15 mol %), and N,N-dimethylethylenediamine (0.12 mmol, 30 mol %) were added and the reaction mixture was heated to 80 C. and kept for 21 hours under nitrogen atmosphere. The mixture was cooled to room temperature, filtered and concentrated to give the title product. The residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether) to give racemic trans-2-(4-chlorophenyl)-1′-(1H-imidazol-4-trityl)spiro[cyclopropane-1,3′-indolin]-2′-one (157 mg, 68%). LC/MS m/e calcd. for C38H28ClN3O: 577, observed (M+H)+: 578.2 MS calcd. for C38H28ClN3O 578, obsd. (ESI+) [(M+H)+] 579.3.

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; Chen, Li; Feng, Lichun; He, Yun; Huang, Mengwei; Yun, Hongying; US2011/144106; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Compound E4 will be dissolved in anhydrous THF at -78 0C and 1 eq of LDA will be added. After 30 min, compound E5 (R8 = H; R10 = 3-MeO-phenyl; R9 = (4-(4- Methylimidazol-1-yl)) will be added. The reaction will be allowed to warm up to r.t. and treated with triflic anhydride (1.1 eq) and triethyl amine before the volatiles will be removed. The residue will be purified to give compound E6 (R8 = H; R10 = 3- MeO-phenyl; R9 = 4-(4-Methylimidazol-1-yl)).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 870837-18-6.

Reference:
Patent; SCHERING CORPORATION; WO2009/5729; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-chloro-1H-benzo[d]imidazole (1.0 eq.) and ethanolamine (10 eq.) was heated to 200 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with water to give desired product 2b. White solid (96% yield); mp 177.4 C; 1H NMR (400 MHz, CD3OD) delta 7.20-7.18 (m, 2H), 6.97-6.95 (m, 2H), 3.75 (t, J = 5.6 Hz, 2H), 3.49(t, J = 5.4 Hz, 2H); LRMS (electrospray) m/z (M+H)+ 178.

The synthetic route of 2-Chloro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Oh, Sangmi; Kim, Sungbum; Kong, Sunju; Yang, Gyongseon; Lee, Nakyung; Han, Dawoon; Goo, Junghyun; Siqueira-Neto, Jair L.; Freitas-Junior, Lucio H.; Song, Rita; European Journal of Medicinal Chemistry; vol. 84; C; (2014); p. 395 – 403;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem