Tag: M.W=200-300

Related Products of 3543-72-4,Some common heterocyclic compound, 3543-72-4, name is Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, molecular formula is C14H17N3O4, 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.

[0075] 163 g (559.5 mmol) of compound (5) were dissolved in 1875 g ethanol. 14 g of palladium catalyst on activatedcarbon doped with iron (5% Pd, 1% Fe) and an additional 0.8 g of iron(II) sulfate 7-hydrate or 0.8 g of iron(III) nitrate 9-hydrate were added. Compound (5) was then hydrogenated at a hydrogen pressure of up to 4 bar until completeconversion of the starting compound (5).[0076] The catalyst was removed by filtration, and the ethanolic solution concentrated until a dry product remained.This residue was crystallized from propan-2-ol or ethyl acetate.[0077] The yield of compound (6) was 128 g (489,8 mmol) with a content of > 99 % (87.5 % of theory).[0078] The overall yield of compound (6) was 80.4% of theory in relation to 2-fluoro-5-nitroaniline. In comparison, thesynthesis according to DD34727 starting from N-1-methyl-4-nitrobenzene-1,2-diamine (CAS 41939-61-1) is characterizedby a yield of 39.0%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(1-methyl-5-nitro-1H-benzo[d]imidazol-2-yl)butanoate, its application will become more common.

Reference:
Patent; HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG; Frey, Michael; Walther, Dirk-Detlef; EP2690096; (2014); A1;,
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Reference of 84946-20-3, These common heterocyclic compound, 84946-20-3, name is 2-Chloro-1-(4-fluorobenzyl)-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.

EXAMPLE 42 To a 25 mL 3-neck flask equipped with a thermometer, reflux consenser and stir bar were added, under a nitrogen atmosphere, 885.6 mg (4.8 mmol) of Compound XXII, obtained according to the procedure of Example 41, and 0.93 mL (8.0 mmol) of lutidine. The mixture was heated to 120 C., whereupon a solution of 1.04 g (4 mmol., 1 eq.) of Compound X (Aldrich Chemical Co., Milwaukee, Wis.), 8 mmol of tetrabutylammonium fluoride (obtained from its 1.0M THF solution by distillation under vacuum with anhydrous toluene) and 4 mL of N-methylpyrrolidinone was added slowly over 2 h. The reaction mixture was allowed to stir at 120 C. for 1 h. High-performance liquid chromatography revealed >95% coversion to Compound XXIII. The reaction mixture was allowed to cool to ambient temperature, and slowly poured into a solution of 5% aqueous NaOH while stirring. The resulting suspension was allowed to stir at 0-10 C. for 30 minutes, and the resulting solid product was collected by vacuum filtration, washed with water (3*5 mL), and air dried for 30 minutes under vacuum to afford crude Compound XXIII: 1 H NMR (300 MHz, CDCl3) delta7.52 (1H, d, J=7.8 Hz), 7.20-7.00 (7H, m, two groups), 5.13 (2H, s), 4.40 (1H, NH br. d), 4.32 (2H, pseudo d), 4.20 (1H, m), 3.00 (2H, pseudo t), 2.15 (2H, pseudo d), 1.30 (2H, m overlapped), 1.26 (9H, s); 13 C NMR (75 MHz, CDCl3) delta176.3, 164.2 and 161.0 (13 C-19 F coupling), 153.3, 142.4, 134.6, 131.4, 128.4, 121.7, 120.0, 116.6, 116.4, 116.1, 107.5, 50.5, 45.1, 44.2, 38.9, 33.1, 28.6. It is to be noted that under the same reaction conditions as above, but without the use of tetrabutylammonium fluoride, only 3.5% conversion (high-performance liquid chromatography) to Compound XXIII was achieved after 3 h at 120 C. The Compound XXIII obtained above was placed in a 50 mL, 3-neck flask equipped with a thermometer, reflux condenser and stir bar. 5 mL of 48% hydrobromic acid was added, and the resulting mixture was heated to 110 C. and allowed to stir at that temperature for 2 h. After the reaction was complete (>98% conversion to norastemizole as shown by high-performance liquid chromatography), the reaction mixture was allowed to cool to room temperature, and 10 mL of toluene and 10 mL of water were added, with stirring.

The synthetic route of 84946-20-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sepracor Inc.; US5817823; (1998); A;,
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Some common heterocyclic compound, 10040-96-7, name is 1-(4-Bromophenyl)imidazole, molecular formula is C9H7BrN2, 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. Application In Synthesis of 1-(4-Bromophenyl)imidazole

General procedure: To a solution of 1-(4-bromophenyl)-N, N-dimethylmethanamine (23.2 mg,0.108 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos)(10.4 mg, 0.018 mmol) and tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (8.3mg, 9.6 mumol) in 1,4-dioxane (1 ml) were added to compound 5(38.2 mg, 0.090 mmol) and N,N-diisopropylethylamine (31.4 mul, 0.180 mmol)and refluxed for 3 h. The mixture was filtrated by either Chromatodisc(0.45 mum) (KURABO INDUSTRIES, Osaka, Japan) or celite. The filtered solidwere washed with MeOH three times and then the assembled solution wasconcentrated under reduced pressure. The resulting residue was purified bypreparative TLC (CHCl3/MeOH/28% aq. NH4OH=10/1/0.1) to obtain thetitle compound as an off-white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10040-96-7, its application will become more common.

Reference:
Article; Wakiyama, Yoshinari; Kumura, Ko; Umemura, Eijiro; Masaki, Satomi; Ueda, Kazutaka; Sato, Yasuo; Watanabe, Takashi; Hirai, Yoko; Ajito, Keiichi; Journal of Antibiotics; vol. 70; 1; (2017); p. 52 – 64;,
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Electric Literature of 84946-20-3, 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 84946-20-3 as follows.

1.2. 1-{1-[(4-Fluorophenyl)methyl]-1H-benzimidazol-2-yl}-N-methyl-4-piperidinamine (method B) 8.7 g (0.05 mole) of 4-methylaminopiperidine (in the form of acetate), 13 g (0.05 mole) of 1-(4-fluorobenzyl)-2-chlorobenzimidazole and 13.8 g (0.1 mole) of potassium carbonate in 250 ml of isoamyl alcohol are brought to reflux temperature for 192 h. The mixture is cooled and evaporated to dryness. The residue is taken up with a mixture of water and ether and agitated until crystallization occurs. The compound (V) obtained in hydrate form is filtered off. The precipitate is taken up with toluene and agitated until dissolution has occurred, and the solution is dried with magnesium sulphate, filtered and evaporated. The residual oil is ground in petroleum ether. The solid product is filtered off and dried. The compound thereby obtained melts at 77-80 C.

According to the analysis of related databases, 84946-20-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Synthelabo; US4820710; (1989); A;,
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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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H9N3

The intermediate materials of Pt(ppy)ppyHCl and Pt(ppy)2C12 may be prepared using a previously reported procedure (Inorg. Chem. 2010, 49, 11297-11308, which is incorporated by reference herein in its entirety). Briefly, a mixture of 2-phenylpyridine and potassium tetrachloroplatinate in tert-butanol and water is heated to reflux to provide Pt(ppy)ppyHCl, which is then reacted with 5H-benzo[d] benzo[4,5]imidazo[1 ,2-a]imidazole in the presence of potassium carbonate in dichloromethane at reflux to provide Compound 301.

According to the analysis of related databases, 28890-99-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Chen, Hsiao-Fan; Silverstein, Daniel W.; Brooks, Jason; Feldman, Jerald; (143 pag.)US2018/331306; (2018); A1;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-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. HPLC of Formula: C11H12BrFN2

3.5 g of 6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole was dissolved in 20 ml of DMF.And add 5.1g of (BPin) 2, 0.62g of PCy3, 3.8g of KOAc and 0.3g of Pd(OAc)2, stir and heat to 100 C for 24h, stop heating and cool down to 6At 0 C, 50 ml of ethyl acetate was added, and the mixture was filtered.Add n-hexane to the oil obtained by concentration, stir and crystallize for 1 h at room temperature.Filtration gave 2.1 g of 4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-boronic acid pinacol ester as a pale yellow solid.

The synthetic route of 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); A;,
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Related Products of 24155-42-8, These common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, 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 2,6-Dichloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:1) 8.7 g of 4-bromomethyl-2,6-dichloroquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g of sodium hydroxide (0.75 mol) dissolved in 30 ml water, 0.5 g of benzyltrimethylammonium chloride and 100 ml of tetrahydrofuran are reacted as described in Example 1. Work up of the mixture results in an oil, which after treatment in boiling ether, is dissolved in 250 ml of ethyl acetate.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4282230; (1981); A;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-48-2, name is 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde, 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 870837-48-2, Formula: C10H7ClN2O

To a THF (13 mL) solution of 3-chloro-4-(1H-imidazol-1-yl)benzaldehyde (545 mg) dimethylphosphonoacetic acid methyl ester (513 muL) and lithium hydroxide monohydrate (133 mg) were added one by one, and the reaction solution was agitated overnight. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 442 mg of crude ester product. 2N sodium hydroxide solution (5.0 mL) was added to the reaction solution obtained by which dissolving the obtained ester product in THF (5.0 mL), and the reaction solution was agitated at room temperature overnight. The reaction solution was cooled to 0 C., 2N hydrochloric acid was added to the reaction solution, and the deposited precipitation was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 218 mg of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 8.08 (d, J=2.0 Hz, 1H), 7.93 (s, 1H), 7.82 (dd, J=2.0, 8.4 Hz, 1H), 7.61 (d, J=16 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.48 (s, 1H), 7.11 (s, 1H), 6.70 (d, J=16 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, 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. Recommanded Product: 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde

2-Methyl-2-butene (5.0 mL), sodium dihydrogenphosphate dihydrate (1.55 g) and sodium chlorite (3.14 g) were added to a solution containing 4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde (2 g) in water (10 mL) and tert-butanol (30 mL), and the reaction solution was stirred for two hours. The generated solid was collected by filtration to obtain the title compound (745 mg). The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 3.89 (s, 3H), 7.09 (s, 1H), 7.54 (m, 2H), 7.63 (dd, J = 8.0, 1.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 8.05 (s, 1H).

The synthetic route of 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde has been constantly updated, and we look forward to future research findings.

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

Reference of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine 110 g (0.45 moles) of formula (XI) was dissolved in 1 L of chloroform. 4-methyl-3-nitro benzoyl chloride of the formula (IIA) prepared above was added slowly to the reaction mass at 10-15 C. for 60 minutes. Reaction mass was raised to room temperature and maintained for 4 hours. Reaction mass was filtered, washed with chloroform and dried.Yield: 161 g (87%) Purity: 99% (by HPLC) [0059] IR and NMR were consistent with the proposed structure.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala; Bhujanga Rao, Adibhatla Kali Satya; Rachakonda, Sreenivas; Gampa, Venugopala Krishna; Nannapaneni, Venkaiah Chowdary; US2013/210847; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem