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. 1544-75-8, name is 5-Fluoro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1544-75-8

A solution of 5-fluoro-1 H-benzo[d]imidazol-2(3H)-one (16.0 g, 105 mmol) in DMF (400 mL) under nitrogen was cooled with an ice-bath, using a mechanical stirrer for agitation. It was then treated over 10 min with sodium hydride (60% w/w in mineral oil, 13.1 g, 327 mmol) and the resulting mixture was stirred at this temperature for 30 min before being treated with iodomethane (26.3 mL, 422 mmol) over 30 min. The resulting mixture was then allowed to warm to room temperature and after 1 h was carefully treated with water (500 mL). The aqueous phase was extracted with EtOAc (3 x 800 mL) and the combined organics were washed with brine (1 L), dried over MgS04 and concentrated in vacuo. Purification of the brown residue by flash chromatography on silica gel (SP4, 1.5 kg column, gradient: 0 to 25% (3: 1 EtOAc/EtOH) in cyclohexane) gave the title compound (15.4 g, 86 mmol, 81 %) as a pink solid. LCMS (high pH): Rt 0.76 min; [M+H+]+ = 181.1 deltaEta NMR (400 MHz, CDCI3) ppm 6.86-6.76 (m, 2H), 6.71 (dd, J = 8.3, 2.3 Hz, 1 H), 3.39 (s, 3H), 3.38 (s, 3H).

The synthetic route of 1544-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BAMBOROUGH, Paul; CHUNG, Chun-Wa; LE GALL, Armelle; SHEPPARD, Robert John; (36 pag.)WO2016/62737; (2016); A1;,
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Application of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-(4-chloro-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Amine 2ag (1g, 4.76mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.4 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10ml) of compound 1a (700 mg, 4.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 360 mg of a white solid. Yield = 19% 1HNMR (DMSO, 200 MHz) delta 1.89 (4H, m), 3.17 (4H, m), 4.30 (2H, d, J = 5.4 Hz), 6.61 (1H, dd, J = 7.6 Hz, J’ = 1 Hz), 6.69 (1H, t), 6.87 (4H, m), 7.24 (1H, d, J = 7.8 Hz), 8.38 (1H, bs), 10.00 (1H, bs), 10.59 (1H, bs); [M+1] 386.7 (C19H20ClN5O2 requires 385.85).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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. Product Details of 2466-76-4

[00123] Methyl 2-(2-bromophenyl)-3-oxobutanoate: A round bottom flask was charged with a magnetic stir bar and methyl 2- (2-bromophenyl) acetate (25 g, 109 mmol) and THF (50 mL). This solution was cooled to -78 ¡ãC before drop wise addition of a 1M solution of LiHMDS in THF (218 ml, 218 mmol). The reaction was stirred for 30 min at -78 ¡ãC before addition of l-(lH-imidazol-l-yl)ethanone (14.42 g, 131 mmol) as a solution in a mixture of THF:DMF (112 mL THF, 24 mL DMF). The solution was stirred for 1 h before quenching with sat’d aqueous NH4C1 (-250 mL) and diluting with EtOAc. The layers were separated and the aqueous phase was extracted with additional EtOAc (~2 x 250 mL). The combined organic extract was washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography using an eluent of ethyl acetate/hexanes (10: 1) to afford methyl 2-(2-bromophenyl)-3-oxobutanoate (32.5 g, 102 mmol, 93 percent ield).

The synthetic route of 2466-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NASVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2015/23915; (2015); A1;,
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Related Products of 4857-06-1, These common heterocyclic compound, 4857-06-1, name is 2-Chloro-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.

General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

The synthetic route of 4857-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
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Synthetic Route of 3304-70-9,Some common heterocyclic compound, 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate, molecular formula is C7H8N2O4, 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 dimethyl 1H-imidazole-4,5-dicarboxylate (1.58g) in water (15mL), was added bromine (4.11g). The mixture was stirred at 60C for Ihr.The solvent was evaporated in vacuo and the residue was triturated with ether to give the target compound (2.35g) as a solid.NMR (DMSO-d6) : d 3.81(6H, s).MASS m/z : 286 (M-l).

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

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; WO2004/108730; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 15813-08-8,Some common heterocyclic compound, 15813-08-8, name is 5-Bromo-4-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.

PREPARATION 705-Bromo-1 ,4-dimethyl-1 H-imidazole To a cooled (0 C) suspension of sodium hydride (60% wt / wt in mineral oil, 149 mg, 3.73 mmol, 1.2 eq.) in anhydrous tetrahydrofuran (10 ml_), under an atmosphere of nitrogen, was added a solution of 5-bromo-4-methyl-1 H-imidazole (500 mg, 3.11 mmol) in tetrahydrofuran (5 ml_). The resulting mixture was stirred at room temperature for 30 min before adding methyl iodide (661 mg, 4.66 mmol, 1.5 eq.). The reaction mixture was stirred for 30 min before partitioning between ethyl acetate (100 ml_) and water (20 ml_). The organic phase was dried over magnesium sulphate and the resulting mixture filtered. The filtrate was evaporated under reduced pressure and the resulting residue purified by chromatography on silica gel (40 g) eluting with a gradient of methanol in dichloromethane (0:100 to 5:95) to give the title compound as a clear oil (80 mg, 15%). 1H NMR (400 MHz, CDCI3): delta = 2.10 (s, 3H), 3.59 (s, 3H), 7.53 (s, 1 H)MS: APCI+ m /z = 174, 176 [MH+]

The synthetic route of 15813-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 10040-98-9, The chemical industry reduces the impact on the environment during synthesis 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, I believe this compound will play a more active role in future production and life.

A mixture of malonitrile (60.0 mg, 0.90 mmol) and 4-(1H-imidazol-1- yl)benzaldehyde (155.0 mg, 0.90 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N- methylmorpholine (0.1 mL, 0.90 mmol) for 2 minutes. To the mixture was added 3-(4- methoxyphenyl)-1-methyl-1H-pyrazol-5(4H)-one (185.0 mg, 0.90 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 48 as an off white solid (360 mg, 94%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.18 (s, 1H), 7.68 (s, 1H), 7.52-7.46 (m, 4H), 7.27 (d, J = 8.0 Hz, 2H), 7.13 (s, 2H), 7.06 (s, 1H), 6.78 (d, J = 8.0 Hz, 2H), 5.06 (s, 1H), 3.77 (s, 3H), 3.69 (s, 3H). MS (ESI): Calcd for C24H20N6O2: 424, found: 424 (M+H)+.

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, 4-Imidazol-1-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; YU, Chengzhi; POLAT, Tulay; YAN, Chao; RABIZADEH, Shahrooz; THEODORESCU, Daniel; (108 pag.)WO2016/205460; (2016); A1;,
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Imidazole | C3H4N2 – PubChem

Application of 26832-08-6, These common heterocyclic compound, 26832-08-6, name is 1H-Imidazole-4-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.

In a dried 125 mL, three-neck flask fitted with a magnetic stirrer, temperature probe, a reflux condenser, and a positive nitrogen atmosphere set-up was charged with 4-imidazole carboxamide 2.0 gm (18 mmol), acetonitrile 25 ml, and POCl3 6.6 gm (43.2 mmol). The brown slurry was agitated and heated to reflux. The reaction mixture was maintained at reflux for at least 15 hrs. Then the excess POCl3 was distilled under reduced pressure. After aqueous work up, the reaction mixture was adjusted to a pH of 9-11 using 25percent sodium hydroxide, and extracted with 4.x.70 ml ethyl acetate. The combine ethyl acetate extracts were treated with 20 gm silica gel, distilled under pressure to remove ethyl acetate and to afford 4-cyanoimidazole as a white solid. After drying the 4-cyanoimidazole weighed 1.1 gm (65.9percent yield): HPLC purity, >99.0 area percent; 1H NMR (300 MHz, DMSO-D6) delta 7.89 (s, 1H), 8.08 (s, 1H); 13C NMR (300 MHz, DMSO-D6) delta 111.8, 116.0, 127, 138.1.

Statistics shows that 1H-Imidazole-4-carboxamide is playing an increasingly important role. we look forward to future research findings about 26832-08-6.

Reference:
Patent; Ampac Fine Chemicals LLC; US2009/292122; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33468-69-8, The chemical industry reduces the impact on the environment during synthesis 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

0.6 g of intermediate 2-3, 4- (trifluoromethyl) imidazole 0.36 g and toluene 0.74 g of potassium carbonate,0.26 mL of trans-N, N’-dimethylcyclohexane-1,2-diamine and 0.15 g of copper iodide were added.The reaction mixture was stirred at 120 C. for 24 hours,After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate.The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 3: 2) to obtain 0.32 g of the active compound A-12 shown below.

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, 4-(Trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; MURAKAMI, SHINICHIRO; (291 pag.)JP2018/76354; (2018); A;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 693-98-1,Some common heterocyclic compound, 693-98-1, name is 2-Methyl-1H-imidazole, molecular formula is C4H6N2, 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: 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.

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

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