Category: imidazoles-derivatives

Synthetic Route of 3034-41-1,Some common heterocyclic compound, 3034-41-1, name is 1-Methyl-4-nitroimidazole, molecular formula is C4H5N3O2, 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.

Mix 1-methyl-4-nitroimidazole (1g), Pd / C (0.1g) and 20ml ethanol,Replace the air with a hydrogen balloon,The reaction was carried out at room temperature for about 24 h.The celite was suction-filtered under reduced pressure, and the filtrate was dried under reduced pressure to obtain the title product (0.75 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-4-nitroimidazole, its application will become more common.

Reference:
Patent; China Pharmaceutical University; Zhang Dayong; Zhang Tiantai; Shu Lei; (27 pag.)CN110330484; (2019); A;,
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, SDS of cas: 288-32-4

Preparatory Example 56 1-(2-Hydroxyethyl)imidazole STR299 3.56 g of 2-bromoethyl t-butyldimethylsilyl ether and 1.97 g of imidazole were dissolved in 70 ml of N,N-dimethylformamide, to which 4 g of potassium carbonate were added, followed by agitation at 90 C. for 2 hours and 40 minutes. After removal of the solvent by distillation, ethyl acetate was added, followed by washing with water and drying with anhydrous magnesium sulfate. This was filtered and, after removal of the solvent by distillation, m the resultant residue was dissolved in tetrahydrofuran, to which 12.6 ml of tetrabutylammonium fluoride (1M tetrahydrofuran solution), followed by agitation at room temperature. After completion of the reaction, the solvent was distilled of and the resultant residue was subjected to silica gel column chromatography (developing solvent: dichloromethane) to obtain 0.59 g of the caption compound (yield 35%). 1 H-NMR(90 MHz, CDCl3) delta:3.28(bs,1H), 3.6-4.2(m,4H), 6.84(bs,1H), 7.28(bs,1H)

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Reference:
Patent; Eisai Co., Ltd.; US5221671; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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.

18(a) Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60 C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167-168 C. (with decomposition). Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.88 (3H, triplet, J=7 Hz); 1.08 (3H, triplet, J=7 Hz); 1.5-1.8 (2H, multiplet); 1.64 (6H, singlet); 2.52 (2H, triplet, J=8 Hz); 4.12 (2H, quartet, J=7 Hz); 5.38 (2H, singlet); 5.78 (1H, singlet); 6.7-7.6 (22H, multiplet); 7.8-8.1 (1H, multiplet).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
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. 3034-38-6, name is 5-Nitro-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3034-38-6

General procedure: The opportune alkyl bromide (916 mg, 4.26 mmol) was added to a solution of 4-nitro-1H-imidazole5 (438 mg, 3.87 mmol) in acetonitrile (3 mL) and potassium carbonate (803 mg, 5.81 mmol).The resulting mixture was heated at 60 C overnight. The reaction mixture was then filtered, andthe filtrate was concentrated in vacuum, leaving a yellow solid. The desired product was recoveredfrom this residue by normal phase column chromatography on a cartridge Biotage HP-SiO2 (50 g)column primed with DCM only. The column was then run for 4CV with DCM and then changed toDCM/MeOH 9:1 over 5CV.1-[2-(2-Methoxyphenyl)ethyl]-4-nitro-1H-imidazole (6a): White solid, 82% yield, mp: 100-102 C; IR: nu= 1338 (NO) cm-1; 1H NMR (400 MHz, DMSO-d6) delta = ppm 3.11 (t, J = 7.34 Hz, 2H), 3.75 (s, 3H), 4.28(t, J = 7.34 Hz, 2H), 6.84 (t, J = 7.34 Hz, 1H) 6.93-7.06 (m, 2H), 7.19-7.26 (m, 1H), 7.67 (s, 1H), 8.30 (s, 1H); 13C NMR (100 MHz, DMSO-d6) delta = ppm 158.8, 146.2, 138.7, 129.9, 128.4, 126.8, 121.5, 120.4, 112.9,56.8, 49.6, 28.6; HRMS (ESI): m/z calcd. for C12H13N3O3 248.9567 [M + H]+, found 248.9542.

According to the analysis of related databases, 3034-38-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Francini, Cinzia Maria; Musumeci, Francesca; Fallacara, Anna Lucia; Botta, Lorenzo; Molinari, Alessio; Artusi, Roberto; Mennuni, Laura; Angelucci, Adriano; Schenone, Silvia; Molecules; vol. 23; 9; (2018);,
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. 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. Quality Control of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Synthesis of (Z)-2-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-4-(3,4,5-trifluorobenzyl)morpholin-3-one Thionyl chloride (16.1 mL) was added to a solution of 2-hydroxy-4-(3,4,5-trifluorobenzyl)morpholin-3-one (3.94 g) in methylene chloride, and the reaction solution was stirred at 50 C. for one hour. The reaction solution was concentrated under reduced pressure, and the residue was diluted with methylene chloride. Then, triphenylphosphine (5.2 g) was added under ice-cooling, and the reaction solution was stirred at room temperature for 4.5 hours. The reaction solution was concentrated under reduced pressure. Ethanol (64.6 mL), TEA (4.2 mL), and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (2.72 g) were added to the residue, and the reaction solution was heated under reflux for two hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with 2 N aqueous hydrochloric acid and ethyl acetate. Then, the aqueous layer was separated. The organic layer was washed with 2 N aqueous hydrochloric acid. Then, the total aqueous layers were combined and made alkaline with a concentrated sodium hydroxide solution. The organic layer was separated by extraction from the alkaline solution with chloroform, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using NH silica gel (heptane:ethyl acetate=1:1 to 0:100) to obtain 1.92 g of the title compound. 1H-NMR (CDCl3) delta (ppm): 2.34(s,3H), 3.56(t,J=4.8 Hz,2H), 3.87(s,3H), 4.28(t,J=4.8 Hz,2H), 4.66(s,2H), 6.93(s,1H), 6.95-6.99(m,3H), 7.23(d,J=8.0 Hz,1H), 7.40(dd,J=8.0,1.2 Hz,1H), 7.42(d,J=1.2 Hz,1H), 7.85(s,1H).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/117798; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 7098-07-9, 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. 7098-07-9, name is 1-Ethyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2.5 equiv. of the corresponding N-imidazole in 5 mL THF in an ACE-pressure tube, 1 equiv. of the dibromo alkyl compound [32] was added. The solution was heated at 100 ¡ãC for 72 h. The solution was filtered and the precipitate was washed with 2 x 5 mL THF and dried under vacuum to yield a white powder.

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

Reference:
Article; Jokic?, Nadez?da B.; Zhang-Presse, Mei; Goh, Serena L.M.; Straubinger, Claudia S.; Bechlars, Bettina; Herrmann, Wolfgang A.; Ku?hn, Fritz E.; Journal of Organometallic Chemistry; vol. 696; 24; (2011); p. 3900 – 3905;,
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. 50995-95-4, name is 2-Propylimidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Propylimidazole

A stirred mixture of [5- (3-FLUORO-4-METHANESULFONYL-PHENYL)-4-METHYL-THIAZOL-2-YL]- (LH-PYRAZOL-3-YL)-AMINE hydrobromide salt (68d) (1.0 g, 2.3 mmol), Caesium carbonate (1.50 g, 4.6 mmol) and 2-propylamidazole (0. 508 g, 4.6 mmol) in dry DMSO (10 ml) is heated at 140 C for 6 hours. After cooling to room temperature the mixture is diluted with ethyl acetate (50 ml) and washed with water (100 ml). The organic extract is separated and the crude product is absorbed on silica. Purification by chromatography on silica, eluting with ethyl acetate-ethanol (1: 1) affords the titled compound.

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 50995-95-4.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/78754; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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 methyltriphenylphosphonium bromide (557mg, 1.56mmol) in THF (8mL) was added 1.0 M NaHMDS solution in THF (1.56mL, 1.56mmol) under argon at O0C. The mixture was stirred at this temperature for 30mins followed by the addition of 1-trityl-1H-imidazole-4-carbaldehyde (440mg, 1.3mmol). The reaction was stirred at O0C to room temperature for 3 hours, quenched with saturated aqueous NH4CI solution, extracted with ethyl acetate (3 x 3OmL). The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography to give 1-trityl-4-vinyl-1H-imidazole (374 mg) with a yield of 86%.

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; S BIO PTE LTD; WO2009/93981; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 22884-10-2, A common heterocyclic compound, 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, molecular formula is C5H6N2O2, 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 50 mL flask was added 4-chloro-orthozide anilide 1d (1 mmol), alpha-bromo-tert-butyl ketone (1.2 mmol), and potassium carbonate (1.5 mmol), which was reacted at 45 C, and the reaction solvent was chloroform ( 20mL), after 2 hours of reaction, Further, diphenylmethylphosphine (1.5 mmol) was added, and the reaction was carried out at 30 C. After the reaction was continued for 3 hours, the solvent chloroform was removed under reduced pressure, and the residue was transferred to triphenylphosphine (2.5 mmol) and iodine. (2.5 mmol) in chloroform (15 mL), Then, imidazoleacetic acid (1.5 mmol) was added, and the reaction was carried out at 45 C for 2 hours. After the reaction was completed, the solvent chloroform was removed under reduced pressure. Residue column chromatography gave 0.206 g of the title compound 2d. The yield was 62%.

The synthetic route of 22884-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Wang Long; Yang Qingqing; Li Yongshuang; Li Dejiang; (8 pag.)CN109265448; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-31-8, name is 5-Chloro-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. name: 5-Chloro-1H-imidazole

Synthesis of 4-chloro-l-(2-methoxy-4-nitrophenyl)-lH-imidazole [0306] To a stirred solution of l-chloro-2-methoxy-4-nitrobenzene (4 g, 39.21 mmol) in DMSO (40 mL) under argon atmosphere were added 4-chloro-lH-imidazole (7.3 g, 39.21 mmol) and potassium hydroxide (2.2 g, 39.21 mmol) at RT. The reaction mixture was stirred at 80 C for 20 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (600 mL), filtered, washed with water (2 x 50 mL) and dried in vacuo to afford 4-chloro-l-(2-methoxy-4-nitrophenyl)-lH-imidazole (3.8 g, 70%) as a brown solid and used without further purification. 1H-NMR (CDC13, 400 MHz): delta 7.98-7.94 (m, 2H), 7.75 (s, 1H), 7.44 (d, 1H), 7.19 (s, 1H), 4.01 (s, 3H); LC-MS: 254.1 (M+l); (column; X-Bridge C-18 (50 3.0 mm, 3.5 muiotaeta); RT 3.05 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 30% EtOAc:hexanes (R/. 0.5).

The synthetic route of 15965-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem