Author: tianli

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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3FN2O2

[0224] To a solution of 4-fluoro-3-nitrobenzonitrile (74.1 mg, 0.446 mmol) and l-(thiophen-2- yimethyl)piperazine (0.081 g, 0.446 mmol) in ACN (1 mL) was added K2CO3 (0.185 g, 1.338 mmol) The reaction mixture was heated to 80¡ãC for 3 hours and then diluted with water (3 mL). The liquid phase was decanted and the solid phase was washed with water and dried in a vacuum oven at 70¡ãC for 4 hours to give the title compound, which was used without further purification.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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 6575-00-4, name: 3,5-Dichlorobenzonitrile

A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a,7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of 5-chloro-3-methoxy-benzonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3695-84-9, name is Methyl 2-cyano-3-phenylacrylate, 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 3695-84-9, Quality Control of Methyl 2-cyano-3-phenylacrylate

General procedure: To a mixture of alkene 1 (0.5 mmol), aldehyde 2 (2.5 mmol), and FeCl2 (1.6 mg, 0.0125 mmol), acetonitrile (3.0 mL) was added under nitrogen at room temperature. Then tert-butyl hydroperoxide 3 (TBHP, 2.0 mmol, 5-6 M in decane) was dropped into the mixture under nitrogen at room temperature. The resulting mixture was stirred under 85 oC for 1 h. The temperature of reaction was cooled to room temperature. The resulting reaction solution was directly filtered through a pad of silica by ethyl acetate. The solvent was evaporated in vacuo to give the crude products. NMR yields are determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether as eluent to afford the pure product 4.

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:
Article; Liu, Kaisheng; Li, Yuanming; Zheng, Xiaojian; Liu, Weiping; Li, Zhiping; Tetrahedron; vol. 68; 50; (2012); p. 10333 – 10337;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 50712-68-0 as follows. COA of Formula: C8H6ClN

Magnesium turnings (0.224 g, 9.35 mmoi) were added to a three neck RBF equipped with nitrogen flow and cold water condenser. Anhydrous THF (25 mL) was added to the reaction mixture and heated at 70-80 C. A solution of 1 -bromo-4-methy3benzene (0.80 g, 4,67 mmol) in THF (10 mL) was added over 20 minutes dropwise to the reaction mixture and the resulting mixture was retluxed at 80 C for 2 h. The resulting gray mixture was cooled to 10 C and used in next step without further purification.(e) (4-chloro-2-methylphenyl)(p-tolyl)methanammeTo a solution of 4-chloro-2~methylbenzonitrile (0.50 g, 3.31 mmoi) in anhydrous THF (15 mL) at 0 C was added solution of >-tolylmagnesium bromide in THF (15 mL) slowly over 10 minutes and the resulting mixture was allowed to warm to rt. The reaction mixture was stirred at rt for 5 h and heated to 60 C where it was further stirred for 2 h. After completion of the imine formation, the reaction mixture was cooled to 0 C and 5 mL of methanol was added very slowly followed by sodium borohydride (0.244 g, 6.62 mmol). The resulting mixture was warmed to rt and stirred overnight. After completion of the reaction, water (10 mL) was added in to the reaction mixture and the mixture was extracted with ethyl acetate (2 X 40 mL). The combined organic layers were washed with brine (25 mL), dried over Na2804, and evaporated to obtained a crude product which was purified using silica gel column chromatography using 10% ethyl acetate in hexanes to obtain the title compound (0.40 g, 40.0%) as a light brown oil. ]H NMR (400 MHz, DMSO-de) delta ppm 7.54-7.56 (d, 1 H), 7.22-7.28 (d, 1 H), 7.15-7.21 (m, 3 H), 7.1 1 -7.13 (m, 2 H), 5.16 (s, 1 IT), 2.24 (s, 3 H), 2.21 (s, 3 IT).

According to the analysis of related databases, 50712-68-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19635; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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: 2-Chloro-4-fluorobenzonitrile

Cool a solution of diisopropylamine (80.6 niL, 0.575 mol) in THF (1 L) to about -5 0C using an ice water/MeOH bath. Add /z-butyllithium (2.5 M in hexanes, 212 mL, 0.530 mol) dropwise over 1 h via a syringe pump (4 mL/min) while maintaining the reaction temperature between -5 to 0 0C during the addition. Stir the lithium diisopropylamide (LDA) solution for 1 h at 0 C and then transfer it via canula, over 1 h, to a -78 0C solution of 2-chloro-4-fluoro-benzonitrile (68.7 g, 0.442 mol) in THF (1 L). Allow the temperature of the reaction mixture to warm to about -65 0C during the initial addition of the LDA solution; however, keep the internal temperature below -70 0C during the remainder of the LDA addition. Keep the temperature of the resulting dark red-orange reaction mixture below -70 0C for 5 h and add iodomethane (251.2 g, 1.77 mol, ~3 mL/min) at such a rate that the reaction temperature is maintained below -65 0C during the addition. Allow the reaction mixture to slowly warm overnight. After stirring for 14 h, the temperature of the reaction mixture is -5 0C. Quench the reaction with saturated aqueous ammonium chloride (500 mL) and water (750 mL) and dilute with diethyl ether (about 2 L). Separate the layers and extract the aqueous layer with diethyl ether (about 1 L). Dry the combined organic layer (about 5.5 L) over MgSO4, filter, and concentrate to afford the crude title compound as a red-brown oily solid (about 86.7 g). Subject the crude residue (dry loaded on silica gel using methylene chloride) to flash chromatography (silica gel (10 x 30 cm), gradient of 99: 1 to 93:7 hexane/EtOAc) to obtain the title compound (56.7 g, 76%) as a white solid, m.p. 63 – 65 0C; 1H NMR (300 MHz, CDCl3): delta 7.54 (dd, J= 8.6, 5.6 Hz, IH), 7.08 (dd, J = 8.6, 8.6 Hz , IH), 2.36 (d, / = 2.4 Hz, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 20 C, 31 g (0.5 mol) of ethylene glycol and 2.4 g (0.06 mol) of 60%(w%) sodium hydride. Then, the temperature was raised to 80 C, and 5.2 g (0.05 mol) of 4-chlorobutyronitrile was rapidly added dropwise. After the addition was completed, the reaction was continued for 30 min. After the reaction mixture was cooled to room temperature, the mixture was extracted twice with dichloromethane. The extract was dried over anhydrous sodium sulfate and evaporated to dryness to give 3.36 g of a pale yellow transparent liquid.Cyclopropionitrile was confirmed by NMR analysis. The yield was 97.2% and the purity was 97%.

The chemical industry reduces the impact on the environment during synthesis 4-Chlorobutyronitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Xi’an Modern Chemical Institute; Li Bingbo; Ning Binke; Zhang Xiaoguang; Chen Tao; Wang Wei; Yang Cuifeng; Qian Yishi; (5 pag.)CN106242997; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1885-38-7, name is (E)-Cinnamonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7N

In accordance with Scheme la, hydrogen chloride is bubbled through a solution ofcinnamonitrile 1 in methanol at room temperature. The volatiles are removed under reduced pressureand the resulting residue is triturated with ether and filtered to yield the intermediate imidate 2. Imidate2 is dissolved in methanol at ambient temperature, treated with amine 4 (commercially available fromAcros Chemicals) at ambient temperature and stirred under argon. The volatiles are removed underreduced pressure and the residue purified by preparative HPLC or trituration with ether to afford amidine3.

The synthetic route of 1885-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/108705; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C7H3ClFN

a 4-Chloro-2-[(3-Hydroxy-1-Phenylpropyl)Amino]Benzonitrile A mixture of 3-amino-3-phenylpropanol (1 g, 6.6 mmol) and 4-chloro-2-fluorobenzonitrile (1 g, 6.4 mmol) in diisopropylethylamine (1.2 ml, 6.9 mmol) was heated at 140 C. for 5 h. The crude reaction mixture was cooled to room temperature and applied to a silica column. The title compound was isolated as a colourless solid (1.1 g, 58%) by elution with 20% diethyl ether/isohexane. MS APCI+vem/z287 ([M+H]+).

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Millichip, Ian; US2003/73685; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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 the N2 environment, compound 3 (0.065 mmol) and 4 (0.390 mmol) were dissolved in 6 mL of chloroform solution.Three drops of pyridine solution were added dropwise, and the mixture was reacted at 75 C for 16 hours. The solvent was evaporated under reduced pressure and purified by residue column chromatography to yield white product NITI-1 (yield 86%).

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; Chinese Academy Of Sciences Chemical Institute; Zhu Xiaozhang; Xu Shengjie; Zhou Zichun; (23 pag.)CN109485635; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 403-54-3, name is 3-Fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4FN

General procedure: CAUTION: Zn(ClO4)2.6H2O can cause skin and serious eye irritation and appropriate care should be taken in its use. In general, perchlorates are explosive compounds and appropriate caution should be taken including the avoidance of evaporation to dryness of perchlorate-containing residues. A mixture of the nitrile (1 mmol), halohydrocarbon (1.2 mmol) and Zn(ClO4)2¡¤6H2O (5 mol%) was placed in a round-bottom flask. Then the reaction mixture was heated at 80 C for the given time. After completion of the reaction (monitored by TLC), water (5mL) was added to the reaction mixture which was then extracted with ethyl acetate (3 ¡Á 5 mL). The organic layers were collected, combined, washed with water (3 ¡Á 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The pure product was obtained by passing the organic extract through a silica gel (200-300 mesh) column using petroleum ether (60-90 C)/ethyl acetate (10:1-5:1) as eluent and identified by 1H NMR and 13C NMR. The 1H NMR and 13C NMR spectra of the products are shown in the Electronic Supplementary Information.

According to the analysis of related databases, 403-54-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Chengliang; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of Chemical Research; vol. 42; 7; (2018); p. 383 – 386;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts