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. 6574-99-8, name is 3,4-Dichlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H3Cl2N

To the reaction vessel of the dry strip rectification column, 350 g of N-methylpyrrolidone (NMP) and anhydrous potassium fluoride (230 g, 3.96 mol) were placed.Add 150g of toluene and reflux to separate water for about 2 hours. After the end of water separation, the toluene is distilled out and recycled for the next application., 3,4-dichlorobenzonitrile (200 g, 1.16 mol), bis-(N,N’-1,3-dimethyl-2-imidazolidinyl)-ammonium chloride (10 g, 0.04 mol) ),Sodium lauryl sulfate (5 g) and sodium thiosulfate (10 g) were heated to 200-210 C for 4 hours.The rectification column received 157 g of a crude product of 3,4-difluorobenzonitrile, and the crude product was subjected to secondary rectification to obtain 146 g of a 3,4-difluorobenzonitrile product having a purity of 99% and a molar yield of 90.7%..

The synthetic route of 6574-99-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Feng Shan Group Co., Ltd.; Chen Baoming; Wang Jinyang; Zhang Qingbao; Ma Tiantian; Dou Feiyang; Yao Jinli; Li Xing; Li Junqing; Wang Bo; Shan Yongxiang; Yin Ping; Yin Fengshan; (8 pag.)CN108409605; (2018); A;,
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Reference of 64113-84-4,Some common heterocyclic compound, 64113-84-4, name is 2-Fluoro-5-methylbenzonitrile, molecular formula is C8H6FN, 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 4-fluoro-3-cyanobenzoic acid To a mixture of 2-fluoro-5-methylbenzonitrile (13.5 g, 0.1 mol), tetrabutylammonium bromide (1.61 g, 5 mmol), and ruthenium(III)chloride trihydrate (0.261 g, 1 mmol) in dichloromethane (150 mL) was added a solution of sodium hypochlorite (645 mL, 0.45 mol) which had been neutralized to pH 9 with 20% sulfuric acid. The reaction mixture was stirred and maintained at pH 9 by adding 20% sodium hydroxide solution at RT. After 3 h, the aqueous phase was separated and neutralized to pH 2 with 20% sulfuric acid and the solid which formed was filtered to give the title compound (3.4 g, 20%). mp 177-8 C. 1 H NMR (CDCl3) delta 7.35 (t, J=8.70 Hz, 1H), 8.38 (m, 1H), 8.42 (m, 1H).

The synthetic route of 64113-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6117866; (2000); A;,
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Synthetic Route of 3672-47-7,Some common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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: Ketonitrile 5 (100 mmol) was added to 15% aqueous NaOH solution(100 mL) followed by hydroxylamine (200 mmol). The resulting mixture was heated at reflux for 14 h, cooled down to r.t., theresulting precipitate was isolated by filtration and crystallized from isopropyl alcohol.

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krasavin, Mikhail; Korsakov, Mikhail; Zvonaryova, Zhanna; Semyonychev, Evgenii; Tuccinardi, Tiziano; Kalinin, Stanislav; Tanc, Muhammet; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 25; 6; (2017); p. 1914 – 1925;,
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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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-(4-Bromophenyl)-3-oxopropanenitrile

To a cooled (0C) and stirred solution of 3-(4-bromophenyl)-3-oxopropanenitrile (Example 230, 4.00 g, 17.85 mmol) in THF (20 mL) was added sodium hydride (60% in oil dispersion, 857 mg, 21.4 mmol). After gas evolution ceased, the mixture was warmed to rt, and isatoic anhydride (3.49 g, 17.85 mmol) was added. The reaction was heated to reflux for 16 h and then cooled to rt. The reaction was quenched and adjusted to pH 5 by slow addition of hydrochloric acid (1 N aqueous solution). The resulting white solid was collected by filtration and triturated with diethyl ether/acetone (3:1) to afford 3.5 g (60%) of desired product. 1H NMR (400 MHz, DMSOd6) delta 12.73 (br s, 1 H), 8.13 (dd, 1 H), 7.70-7.87 (m, 6 H), 7.49 (dddd, 1 H); ES-MS m/z 326.8 [M+H]+, HPLC RT (min) 2.95

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; BAYER PHARMACEUTICALS CORPORATION; WO2006/34491; (2006); A2;,
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Reference of 64248-62-0, The chemical industry reduces the impact on the environment during synthesis 64248-62-0, name is 3,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

40 mL of N,N-dimethylformamide was placed in a 250 mL four-necked flask.R-(+)-2-(4-hydroxyphenoxy)propionic acid butyl ester 34g (0.14 mol),3,4-difluorobenzonitrile 24g (0.168mol),Phase transfer catalyst 18-crown-6 0.15g, TEBA 0.15g,With stirring, 58 g (0.42 mol) of potassium carbonate was added, and a large amount of bubbles were generated;Then the temperature was raised to 85-90 C, the reaction was kept for 3 hours, and the sample was analyzed by HPLC.R-(+)-2-(4-hydroxyphenoxy)propionic acid butyl ester <0.5%, the reaction was completed.Filtration, distilling off the solvent under reduced pressure, and cooling to room temperature with 150 mL of water.The temperature is raised to 60-70 C, the mixture is completely dissolved, and the layer is allowed to stand.Wash with 100 mL of water and de-dissolve to dryness to give an oil.That is, the original drug of cyhalofop-butyl ester 49.5g, the yield: 98.9%, the content: 98.0%,Optical 97.2%. 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-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Jiangsu Zhongqi Technology Co., Ltd.; Zhang Sheng; Zhang Pu; Wang Yuchi; Chen Wen; Wang Fengyun; Hou Yuanchang; (6 pag.)CN109651140; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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 179898-34-1, Recommanded Product: 3-Bromo-5-fluorobenzonitrile

A solution of 3-bromo-5-fluorobenzonitrile (CVII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL¡Á3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CVIII) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+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; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (268 pag.)US2016/68529; (2016); A1;,
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These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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. Formula: C11H13NO3

Following procedures similar to that of Step D but substituting 3,4,5-trimethoxyphenylacetonitrile for 3-methoxy-5-(methylthio)-4-propoxyphenylacetonitrile, there was prepared ethyl 3,4,5,-trimethoxy-alpha-cyanobenzeneacetate in 89% yield as a clear oil. NMR (CDCl3): delta 1.35 (t, 3H, -CO2CH2C H 3), 4.25 (q, 2H, -CO2C H 2CH3), 4.65 (s, 1H, -C H (CN)CO2Et), 6.05 (s, 2H, Ar-H).

The synthetic route of 3,4,5-Trimethoxyphenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; EP257921; (1988); A2;,
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Related Products of 16588-02-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: In a typical experiment, p-CNB (1 g, 6.35 mmol), CuI (0.635 mmol),commercial 25% aqueous NH3 solution (10 mL, NH3/p-CNB molar ratio21/1) were loaded into a 50 mL stainless steel reactor and sealed. Thematerial of the autoclave used is AISI 316 L, for which the compositionis Cr 16-18%, Ni 10-14%, Mo 2-3%, MnQ2%, Si Q1%, CQ0.03%,SQ0.03%, PQ0.045%, and the other part is Fe. After being heated to200 C, the reaction was conducted while stirring with a magneticstirrer (1200 rpm). The pressure of the vapor phase (NH3 and H2O) wasabout 3 MPa at the reaction temperature. After stirring for 1 h, the reactorwas cooled to room temperature and the reaction mixture wasseparated by centrifugation. The solid substrate and product were dissolvedin ethanol and analyzed by a gas chromatograph (Shimadzu GC-2010) equipped with a capillary column (Rtx-5 capillary column: 30m¡Á0.25mm ¡Á0.25 Tm, carrier: N2) and a flame ionization detector(FID) and gas chromatograph-mass spectrometer (GC-MS, Agilent 5890,HP-5). o-Xylene was used as an internal standard for quantitativeanalysis. The liquid phase was also analyzed by gas chromatograph andno p-CNB or p-NAN were detected. The carbon balance was near 99%and trace amount of other unidentified byproducts were observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Li, Yan; Shi, Ruhui; Lin, Weiwei; Cheng, Haiyang; Zhang, Chao; Arai, Masahiko; Zhao, Fengyu; Molecular catalysis; vol. 475; (2019);,
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Synthetic Route of 185836-35-5, 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 185836-35-5 as follows.

A mixture of 0.93 g of lithium aluminum hydride and 30 ml ofTHF was stirred under cooling on ice. Thereafter, a mixture solution of 2.8 g of 4-benzyloxy-2-fluorobenzonitrile and 10 ml of THF was added dropwise to the reaction mixture. The obtained mixture was stirred at a room temperature for 6 hours. Thereafter, the reaction mixture solution was cooled to 0C. 0.9 ml of water, 0.9 ml of a 15% sodium hydroxide aqueous solution, and 2.7 ml of water were successively added to the reaction mixture, and the obtained mixture was stirred at a room temperature for 1 hour. Thereafter, the reaction mixture was filtrated through Celite (registered trade mark), and it was then concentrated under reduced pressure, so as to obtain 2.5 g of 4-benzyloxy-2-fluorobenzylamine.4-benzyloxy-2-fluorobenzylamine [Show Image] 1H-NMR (CDCl3) delta: 3.82 (2H, s), 5.04 (2H, s), 6.67-6.75 (2H, m), 7.18-7.24 (1H, m), 7.32-7.45 (5H, m).

According to the analysis of related databases, 185836-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2248423; (2010); A1;,
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Some common heterocyclic compound, 5332-06-9, name is 4-Bromobutanenitrile, molecular formula is C4H6BrN, 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-Bromobutanenitrile

Preparation of 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyronitrile (Compound 35) A solution of 4-bromo-butyronitrile (300 mg, 2.02 mmol) and sodium azide (263 mg, 4.05 mmol) in acetone (10 ml) is refluxed for 12 hours under nitrogen atmosphere, cooled to room temperature, filtered, and the solvent is removed under vacuum to give 4-azido-butyronitrile as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-06-9, its application will become more common.

Reference:
Patent; Gelder, Joel M. Van; Klein, Joseph Y.; Basel, Yochai; Reizelman, Anat; Tchilibon, Susanna; Mouallem, Orly; US2008/39456; (2008); A1;,
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