Author: Jessica.F

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

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

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

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

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

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

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

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, Application In Synthesis of 1H-Imidazole

General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 M%) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.

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; Anitha, Panneerselvam; Manikandan, Rajendran; Viswanathamurthi, Periasamy; Journal of Coordination Chemistry; vol. 68; 19; (2015); p. 3537 – 3550;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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. category: imidazoles-derivatives

Preparation of a cucurbituril trimer (Figure 23, Compound 38) :; As is exemplified in Figure 23, an exemplary pathway for forming a cucurbituril trimer involves a disubstituted cucurbituril derived from benzil. Such a pathway generally includes preparation of a benzil-derived glycoluril, as described hereinabove, a formation OF A DERIVATIZED CB monomer, and a trimerization step. As a starting material, a benzil-derived glycoluril (Figure 23, Compound 35) is prepared by reacting a para-substituted benzil with urea in a 1: 2 ratio in benzene and trifluoroacetic acid, according to the exemplary syntheses are presented hereinabove. In one non-limiting example, one of the para-substituents on the benzil is a carboxyl group and the second is hydrogen (Figure 23, Compound 34). Compound 35, is reacted with glycoluril, Compound 2, in a 1: 5 ratio, and with formaldehyde, in the presence of concentrated sulfuric acid, to thereby form the derivatized cucurbituril biphenyl-CB [6] (Figure 23, Compound 36). Compound 36 is reacted with 1,3, 5-benzenetriamine (BTA) in a 3: 1 ratio so as to form three amide bonds between each of the carboxyl groups on the derivatized CB [6] and an amine on the BTA, and thus form a cucurbituril trimer having a BTA as the assembling unit (Figure 23, Compound 38).

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TECHNION RESEARCH & DEVELOPMENT FOUNDATION LTD.; WO2005/23816; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

EXAMPLE 2: 3-(4-Bromo-benzyl)-5-(1-hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazol-4-carboxylic acid ethyl ester (IV; X=Br) 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%.

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; Dipharma Francis S.r.l.; EP1905770; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem