Category: nitriles-buliding-blocks

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. 42186-06-1, name is 2-(4-Bromophenyl)propanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(4-Bromophenyl)propanenitrile

[00820] Example 42. Preparation of N-((6-(3-t°r^butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-l(2H)-yl)-2- methoxyphenyl)benzo[c/]isoxazol-3-yl)methyl)methanesulfonamide (compound IB-LO-2.45).; [00821] Part A. Preparation of N-((6-bromobenzo[(f]isoxazol-3-yl)methyl)-N-(4-methoxybenzyl)- methanesulfonamide.; [00822] To a refluxing solution of 6-bromo-3-methylbenzo[d]isoxazole (LOg, 4.72mmol) in CCl4 (25ml) was added l-bromopyrrolidine-2,5-dione (0.923g, 5.19mmol) and benzoic peroxyanhydride (0.114g, 0.472mmol). The mixture was refluxed for 6h, and then cooled to room temperature, filtered thru celite, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using CH2Cl2 as the eluent to give the dibromide as a solid (0.84g, 43%). To a solution of the dibromide (0.2Og, 0.687mmol) and N-(4-methoxybenzyl)methanesulfonamide (0.148g, 0.687mmol) in EtOH (3ml) was added IN aq. NaOH (0.722ml, 0.722mmol), and the resulting mixture was stirred at 8O0C for 90min. The mixture was partitioned between 0.1nu aq. HCL (1OmL) and EtOAc (2 x 1OmL), and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 2:3 EtOAc:hexanes as eluent to give the title compound as an oil (65mg, 22%).

The synthetic route of 42186-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/39134; (2009); A1;,
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Application of 10444-38-9,Some common heterocyclic compound, 10444-38-9, name is Ethyl 4-cyanobutanoate, molecular formula is C7H11NO2, 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 a solution of the cyano ethyl esters (4.8mmol) in pyridine (26ml) were added water (13ml), acetic acid (13ml), sodium hyposphite (39.06mmol) and Raney nickel. The suspension was then stirred at 40C for 2hr. The catalyst was removed by filtration, and washed with ethanol (5ml). Water (300ml) and diethyl ether (80ml) were added to the filtrate, and the organic layer was separated. The aqueous phase was further extracted with diethyl ether (2x80ml), and the combined extracts were washed with water (300ml), and brine (100ml), and dried over Na2SO4 anhydrous, concentrated under vacuo, and the residue was purified by silica gel dry column vacuum chromatography ( DCVC) by stepwise gradient elution with dichloromethane/hexane (50:50 to 100:0).

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; UNIVERSITY OF TECHNOLOGY SYDNEY; VANDENBERG, Robert; RYAN, Renae Monique; RAWLING, Tristan; IMLACH, Wendy; CHRISTIE, Macdonald; CARLAND, Jane; MOSTYN, Shannon; (169 pag.)WO2018/132876; (2018); A1;,
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Related Products of 143306-27-8, These common heterocyclic compound, 143306-27-8, name is 2-Fluoro-6-nitrobenzonitrile, 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.

Method AA Al 05 (500 mg), l-methyl-(4-methylamino)piperidine (440 muL) and Hnig base (600 muL) are suspended in 1.5 mL butanol and stirred for 1 h at 150 0C in a Biotage microwave. The reaction mixture is combined with water and DCM, the organic phase is separated off and dried.

The synthetic route of 143306-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/152014; (2008); A2;,
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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 191014-55-8 as follows. Recommanded Product: 4-Fluoro-2-methoxybenzonitrile

To a solution of 0.7 g of 1-[4-methyl-2-(4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propan-1-ol in 3 mL of dimethylformamide at 5 C. was added 113 mg of a 55% suspension of sodium hydride in mineral oil. The reaction mixture was stirred for 30 minutes at 5 C. The resulting mixture was slowly added to a solution of 429 mg of 4-fluoro-2-methoxy-benzonitrile in 1 mL of dimethylformamide at 5 C. The resulting mixture was stirred at 5 C. allowing the temperature to warm up to room temperature. It was then heated in a sealed tube to 60 C. under microwave irradiation for 15 minutes. After allowing it to cool down to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 50/ethyl acetate 50) to give 1.05 g of 2-methoxy-4-{1-[4-methyl-2-(trans-1,4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propoxy}-benzonitrile.C22H25F3N2O3 (422.45), MS (ESI): (M+H+) 423.4 (M+H+).

According to the analysis of related databases, 191014-55-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); A1;,
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These common heterocyclic compound, 80517-21-1, name is 4-Fluoro-2-nitrobenzonitrile, 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-Fluoro-2-nitrobenzonitrile

4-fluoro-2-nitrobenzonitrile (0.2 mmol, 33.2 mg), tetrahydroxydiboron (0.6mmol, 53.8 mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), Benzaldehyde (0·24mmol, 25·4mg), methanol (1ml), water (1ml) were added to the test tube, reacted at 60 C for 3h, after the completion of reaction, the reaction solution was extracted with ethyl acetate three times, the combined organic phases are concentrated to dryness, separated through column chromatography (petroleum ether: ethyl acetate =4:1), Yield:(45.0mg,93%)

The synthetic route of 4-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Zhou Haifeng; Sui Yuebo; Jiang Xiaolan; Yang Bing; Yu Tao; (16 pag.)CN108558778; (2018); A;,
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Application of 129931-47-1, 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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Stage 1 1-(2-chloro-6-cyano-4-trifluoromethylphenyl)-5-(2-hydroxyisopropyl)-4-trifluoromethylpyrimidin-6-one was prepared from 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 5-(2-hydroxyisopropyl)-4-trifluoromethyl-pyrimidin-6-one (Preparation 2) according to the general method disclosed in EP 0 398 499 for the preparation of Compound A1 in Table A1. Melting Point: 125.6 – 127.6C, 1H NMR delta(CDCl3): 8.14(s,1H); 8.05(s,1H); 7.99(s,1H); 3.45(s,1H); 1.75(d,6H).

The synthetic route of 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; EP481604; (1992); A1;,
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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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-3-nitrobenzonitrile

Example 1732- [4-(l-Benzofuran-5-yl)phenyl]-l-{[(3S)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl] methyl}- lH-benzimidazole-7-carbonitrile(a) 2-({[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amino)-3- nitrobenzonitrileA mixture of {[(3S)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amine (553 mg, 3.29 mmol), 2-chloro-3 -nitrobenzonitrile (500 mg, 2.74 mmol), and DIEA (1.431 mL, 8.22 mmol) were dissolved in 1,4-dioxane (10 mL) in a microwave Vial. The mixture was heated at 150 C for 1 hour. The mixture was evaporated, taken up in DCM and washed with water. The aqueous layer was extracted with DCM and the combined organics evaporated and purified by silica gel column chromatography using a gradient of 0-5% MeOH/DCM to afford the titled compound (800 mg, 2.55 mmol, 93 % yield) as an orange solid. 1H NMR (400 MHz, chloroform-d) delta ppm 0.71-0.88 (m, 2 H) 0.94-1.12 (m, 2 H) 1.59-1.69 (m, 1 H) 1.69-2.00 (m, 1 H) 2.11-2.41 (m, 1 H) 2.55-2.92 (m, 0 H) 3.16-4.11 (m, 6 H) 6.80 (ddd, J=10.04, 8.40, 7.58 Hz, 1 H) 7.79 (ddd, J=9.35, 7.71, 1.39 Hz, 1 H) 8.27- 8.49 (m, 1 H) 8.53-8.80 (m, 1 H).

According to the analysis of related databases, 34662-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HALLMAN, Jason; LAUDEMAN, Christopher; LIU, Ronggang; MILLER, Aaron; MOORE, Michael, Lee; DOCK, Steven; MUSSO, David; PARRISH, Cynthia; WO2011/56635; (2011); A1;,
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These common heterocyclic compound, 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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. Quality Control of tert-Butyl 4-cyanobenzylcarbamate

To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75C for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N’-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

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

Reference:
Patent; Kaken Pharmaceutical Co Ltd; kegami, Satoru; Watanabe, Atsushi; Hirano, Kimio; Oyama, Tadashi; (62 pag.)KR2016/18745; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 914250-82-1, name is 3-Bromo-2-chlorobenzonitrile, belongs to nitriles-buliding-blocks 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 914250-82-1, COA of Formula: C7H3BrClN

Description for D14 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (D14) A mixture of 3-bromo-2-chlorobenzonitrile (2.0 g), sodium bicarbonate (1.55 g) and hydroxylamine hydrochloride (1.28 g) in ethanol (50 ml.) was heated at reflux for overnight. The inorganic precipitate was filtered off. The solid was washed thoroughly with ethanol. The filtrate was concentrated. The obtained solid was dried in vacuo to afford 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (2.13 g). MS (ES): C7H6BrCIN2O requires 248; found 249.1 (M+H+).

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:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; MENG, Qinghua; REN, Feng; XIANG, Jianing; XU, Heng; ZHAO, Baowei; ZHANG, Haibo; WO2010/148649; (2010); A1;,
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Application of 5312-97-0, 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 5312-97-0 as follows.

To solution of 2,5-dimethoxybenzonitrile (1.5 g) in dry Et2O (7 mL) was added propyl magnesium chloride (2 M in Et2O, 9.2 mL) and the resulting mixture was heated to 40 C. for 2 h. The mixture was chilled and 4 M HCl (9 mL) was carefully added and it was stirred at ambient temperature for 16 h. The mixture was extracted with EtOAc, the combined organic layers were washed with water, were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (Interchim cartridge 15SiHP/120 g, Cy/EtOAc) to yield the desired compound (57% yield). [0569] LC-MS (Method 1): m/z [M+H]+=209.3 (MW calc.=208.25); Rt=3.5 min

According to the analysis of related databases, 5312-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
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