Category: imidazoles-derivatives

Application of 3304-70-9, These common heterocyclic compound, 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, 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.

a) dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate 9.50 g bromine in 100 ml dichloromethane are added dropwise to a mixture of 9.90 g methyl 1H-imidazole-4,5-dicarboxylate and 7.46 g potassium carbonate in 200 ml dichloromethane and 80 ml acetonitrile. The mixture is stirred for 12 h at ambient temperature in the dark and then added to a saturated aqueous solution of sodium thiosulphate and sodium chloride. The organic phase is separated off and the aqueous phase is extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulphate and the solvent is removed. Yield: 12.31 g (87% of theory) Mass spectrum (ESI+): m/z=263/265 (Br) [M+H]+

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203095; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1615-14-1, A common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

1-(Hydroxyethyl)imidazole (5.30 g; 47.3 mmol) was dissolved in anhydrous THF (50 mL) and cooled in an ice-bath. Sodium hydride (2.08 g of a 60 wt % dispersion in oil, 52.0 mmol) was added in portions over 10 min. The ice-bath was removed, and the mixture was stirred at room temperature for 20 min. A solution of 1-fluoro-4-nitrobenzene (5.0 mL, 47.2 mmol) in anhydrous THF (10 mL) was added over 5 min and the mixture stirred for a further 1.5 hr. Water (a few mL) was cautiously added and the mixture concentrated under reduced pressure. The residue was partitioned between EA (75 mL) and water (75 mL), and the phases separated. The aqueous phase was extracted twice with EA and the combined organic layers extracted three times with 1N hydrochloric acid. The pH of these acidic extracts was then adjusted to 7 with 5N aqueous sodium hydroxide and the resulting milky solution extracted three times with EA. The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated under reduced pressure to give 1-(2-(4-nitrophenoxy)-ethyl)-1H-imidazole (5.46 g) as a brown oil. A solution of 1-(2-(4-nitrophenoxy)ethyl)-1H-imidazole (5.46 g; 2.34 mmol) in ethanol (60 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.40 g) at room temperature for 20 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[2-(1H-imidazol-1-yl)ethoxy]benzenamine (4.56 g) as a white 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; Telik, Inc.; US2010/81653; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1632-83-3,Some common heterocyclic compound, 1632-83-3, name is 1-Methylbenzimidazole, molecular formula is C8H8N2, 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: The product 7h is a representative reaction. To a screw-cappedvial (5 mL) containing Ni(COD)2 (14 mg, 0.05 mmol), IMes (14 mg, 0.05 mmol),benzimidazole (66 mg, 0.50 mmol), and potassium tert-butoxide (5.6 mg, 0.05 mmol)was added toluene (1.0 mL) followed by the addition of 1,5-cyclooctadiene (43 mg,0.04 mmol) in a glove box atmosphere. The reaction vial was closed and heated at 80o C for 2 hours outside of the glove box. The resulting mixture was filtered throughCelite and washed with dichloromethane. The filtrate solution was concentrated invacuo to afford the crude product, which was further purified by columnchromatography using hexane/ethyl acetate (4:1 v/v) as eluent to furnish(E)-2-(cyclooctenyl)-1-methyl-benzimidazole 7h (117 mg) in 97% yield.The compound 7i was synthesized via similar conditions (see Table 3)._(E)-2-(cyclooct-1-en-1-yl)-1-methyl-1H-benzo[d]imidazole (7h): 1H NMR (300MHz, CDCl3): delta 7.75-7.71 (m, 1H), 7.25-7.19 (m, 3H), 6.06 (t, J = 8.1, 1H), 3.72 (s,3H), 2.75-2.71 (m, 2H), 2.36 (dd, J = 8.1, 11.4, 2H), 1.66-1.59 (m, 8H). 13C NMR (75MHz, CDCl3): delta 155.6, 142.4, 136.1, 135.8, 131.6, 122.1, 121.8, 119.3, 109.2, 31.6,29.3, 29.0, 28.9, 26.9, 26.4, 26.1. HR-MS (EI): calculated for: [C16H20N2]+: 240.1626.Found: 240.1620.

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

Reference:
Article; Lee, Wei-Chih; Shih, Wei-Chin; Wang, Ting-Hsuan; Liu, Yuhua; Yap, Glenn P.A.; Ong, Tiow-Gan; Tetrahedron; vol. 71; 26-27; (2015); p. 4460 – 4464;,
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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-1H-benzo[d]imidazole

(2) Synthesis of intermediate (C-2); [0080][Chem. 12] Intermediate (C-2); [0081] 2-Chloro-benzimidazole (20 g (131 mmol, trade name: 2-Chlorobenzimidazole, manufactured by Aldrich) and THF (150 mL) were placed in a 500-mL three-neck flask, and t-butoxy sodium (13.8 g (144 mmol)) was added thereto under ice cooling. The mixture was stirred at room temperature for 1 hour. Subsequently, a solution of methyl iodide (24.2 g (170 mmol)) and THF (30 mL) was dropped into the flask under ice cooling, and the resulting mixture was stirred at room temperature for 5 hours. The reaction solution wasextracted with chloroform, followed by drying over anhydrous sodium sulfate. Subsequently, the solvent was removed to obtain 18.6 g (yield: 85%) of an intermediate (C-2) (2- chloro-1 -methyl- lH-benzimidazole, white crystal) .

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; CANON KABUSHIKI KAISHA; MUTA, Hajime; SEKIGUCHI, Takeshi; ISHII, Ryuji; SUZUKI, Koichi; WO2011/122381; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]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. COA of Formula: C8H7BrN2

[000388j To a stirred solution of compound 1 (1.6 g, 1 eq) in aq. ammonia solution (5 mL), copper chloride (catalytic amount) was added and heated at 90 C in a sealed tube for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20% methanol in dichloromethane and filtered. The filtrate was evaporated under reduced pressure to afford the title compound 2. LCMS (mlz): 148.00 (M + 1).

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic 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 641571-13-3, Product Details of 641571-13-3

(VII) (10 g), t-butanol (300 mL), triethylamine (7.9 g) and diphenylphosphoryl azide (11.2 g) were added to a 500 mL reaction flask.The mixture was heated to reflux and refluxed for 16 hours then cooled to room temperature. The solvent was removed by evaporation under reduced pressure. The residue was treated with water (150 mL) and extracted with ethyl acetate (2 x 150 mL).The extracts were combined, washed with brine (150 mL), dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to give the crude product (12.1 g). The crude product obtained in Example 1 (12.1 g) was chromatographed (silica gel eluting with ethyl acetate containing 2% ethanol) to give two components which were each recrystallized from ether-hexane to give a solid compound ( II) (5.25 g) and the solid compound (III) (3.76 g).

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, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Esteve Huayi Pharmaceutical Co., Ltd; Zhao, Liqiang; Wang, Zhao; Jiang, Hong; Dong, Jin; Xu, Xiaofei; Zheng, Guorong; (9 pag.)CN105985293; (2016); A;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Nitro-1H-imidazole

5-Nitroimidazole (2) (1 g, 8.85 mmol) and dimethyl sulfate (1.2 mL) were added in dioxane (5 mL). Reaction mixture was refluxed for 2 h. The solvent was then evaporated under vacuum, and the oily acidic residue was neutralized by a NaHCO3 saturated aqueous solution. The formed solid and the aqueous solution were extracted with dichloromethane (3 x 5 mL). Mixture was dried with magnesium sulfate and organic solvent evaporated on vacuum, crude was purified using flash column chromatography (dichloromethane/ethylacetate; 97:3) to obtained 1-Methyl-5-nitro-1H-imidazole (4a) (0.92 g, 82%); m.p. 60 C.

The synthetic route of 3034-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Samant, Bhupesh S.; Sukhthankar, Mugdha G.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1015 – 1018;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 116568-17-3, name is 1H-Benzo[d]imidazole-6-carboxamide, 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. category: imidazoles-derivatives

EXAMPLE 23 1-(6-{[(1S)-1-(3-Fluorophenyl)ethyl]amino}pyrazin-2-yl)-1H-benzimidazole-6 carboxamide: To a stirred mixture of 6-chloro-N-[(1S)-1-(3-fluorophenyl)ethyl]pyrazin-2-amine (242 mg, 0. 96 mmol) and 5-benzimidazole carboxamide (318 mg, 1. 97 mmol, 2, 1 eq) in 18 dimethylformamide (5 mL) was added cesium carbonate (460 mg, 1.41 mmol, 1.5 eq). This solution was then heated at 120C under a nitrogen atmosphere for 48 hours at which time a second amount of cesium carbonate (180 mg, 0. 6 eq) was added. The mixture was heated at 120C for a further 62 hours before being cooled to room temperature, diluted with chloroform (15 mL) and filtered, The filtrate was then concentrated in vacuo and subjected to silica column chromatography (stepwise gradient from dichloromethane to 9: 1 dichloromethane : methanol) to yield the 5-carboxamide product (100. 7 tng, 28%) along with the desired 6-carboxamide product (63.7 mg, 18%). ‘H NMR (d6-acetone, 300 MHz) No. 1.64 (3H, d, J = 6. 9 Hz), 2.76-2. 80 (2H, brm), 5.35 (1H, m), 6.93 Cm, m), 7. 29-7. 36 (3H, m), 7. 42 (1H, dm,/= 7. 7 I Iz), 7. 77 (1H, dd, J = 8.5, 0.5 Hz), 7.93 (1H, dd, 1. 7, 8. 5 Hz), 8.05 (1H, s), 8. 31 (1H, s), 8. 73 (1H, s), 8.40 (1H, dd, J = 0. 5, 1. 6 Hz). MS (c. i.) m/z 376 (M+, 89%).

The synthetic route of 1H-Benzo[d]imidazole-6-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYTOPIA RESEARCH PTY LTD; WO2005/54230; (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. 25676-75-9, name is 4-Bromo-1-methylimidazole, A new synthetic method of this compound is introduced below., Product Details of 25676-75-9

General procedure for preparation of Compound 10-6: A solution of Compound 10-3 (169 mg, 0.3 mmol) in a mixture of dioane (10 mL)-H20 (1 mL), was added Compound 10-5 (55.8 mg, 0.3 mmol), Cs2C03 (195 mg, 0.6 mmol) and Pd(dppf)Cl2 (22 mg, 0.03 mmol) and heated under irradiation of M W at 130C for 30 min under N2. Catalyst was filtered through diatomite and concentrated in vacuum to give the crude product (100 mg, yield 61.3%).

The synthetic route of 25676-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC; CHEN, Huifen; CRAWFORD, Terry; MAGNUSON, Steven, R.; NDUBAKU, Chudi; WANG, Lan; WO2013/113669; (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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H4N2

(1) will p-nitrochlorobenzene 0.158g (1.0mmol), imidazole 0.069g (1.0mmol), Cu (OAc)2·H2O 0.030g (0.15mmol), 2,2- biimidazole 0.022g (0.15mmol), cesium carbonate 0.652g (2mmol), DMSO (2mL) was added the reaction tube with a piston, was heated to 80 deg.] C with stirring for 48 hours reaction.(2) TLC until the reaction was complete the reaction was followed ends.After the reaction was cooled to room temperature, diluted with water, extracted with ethyl acetate 3-4 was added, and the combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product.After the end of (3) to obtain the crude product was purified by column chromatography (petroleum ether / ethyl acetate elution) to give the desired product 17 (79% yield).

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; Soochow University (Suzhou); Zeng Runsheng; Zhou Chunmei; Zou Jianping; (15 pag.)CN104447557; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem