Month: May 2021

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 1897-52-5 as follows. COA of Formula: C7H3F2N

4.00 g (35.65 mmol) of potassium tert-butoxide and 2.60 g (34.64 mmol) of acetohydroxamic acid are dissolved in 50 ml of dry dimethylformamide and stirred at room temperature for 45 minutes. After the addition of 3.30 g (23.72 mmol) of 2,6-difluorobenzonitrile, the mixture is stirred at 50 C. for 16 hours. The mixture is concentrated under reduced pressure, and the residue is dissolved in dichloromethane and washed with water. After drying and concentration of the organic phase, 3.2 g of a yellow resin are obtained, which, according to 1H NMR, is about 85% pure

According to the analysis of related databases, 1897-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/267703; (2010); A1;,
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Nitriles – Chemistry LibreTexts

Electric Literature of 55490-87-4, 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. 55490-87-4, name is 2-(Anthracen-9-ylmethylene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of beta-cyanostyrenes 1 (1.0 mmol) and PIDA 2a (386 mg, 1.2 equiv) in acetonitrile and water (1:1) (5 mL) was irradiated in ultrasonic bath (Power dissipation as 50 W and frequency of 40 kHz) at room temperature for 30-60 min. The course of reaction was monitored by TLC. After completion of reaction, water (5 mL) was added to the reaction mixture and extracted with dichloromethane (3 X 5 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum. The crude products were purified by column chromatography on silica gel using EtOAc-hexane (1:49) and isolated products were characterized as beta-cyanoepoxides 3 by their spectroscopic analysis.

The synthetic route of 2-(Anthracen-9-ylmethylene)malononitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Fateh V.; Mangaonkar, Saeesh R.; Kole, Priyanka B.; Synthetic Communications; vol. 48; 17; (2018); p. 2169 – 2176;,
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Electric Literature of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2H-l,3-benzodioxole-5-carbonitrile (1.73 g, 11.75 mmol) in diethyl ether (15 ml) was added portion wise to a mixture of lithium aluminiumhydride (55.2 mmol hydride, 13.8 mmol, 525 mg) in diethyl ether (15 ml). The mixture was refluxed for 2 hours, then cooled and worked up (H20, 15 % NaOH, 3 x H20) and gave crude benzyl amine (1.77 g, quant.). This amine (1.0 g, 6.6 mmol) and pyridine (1.1 equiv., 17.6 mmol, 1.43 ml) was dissolved in dichloromethane (5.0 ml) and added dropwise to an ice cooled mixture of triphosgene (2.7 mmol, 801 mg,) in dichloromethane (5.0 ml). The mixture was stirred for 1 hour, then partitioned between cold 0.5 M sulfuric acid and dichloromethane. The organic phase was separated, dried and evaporated to give crude 5-(isocyanatomethyl)-2H-l,3-benzodioxole (1.08 g, 92 % yield). (0987) [00644] N-[(2,4-difluorophenyl)methyl]-l-methylpiperidin-4-amine (250 mg, 1.01 mmol) was dissolved in dichloromethane (1 ml) and 5-(isocyanatomethyl)-2H-l,3-benzodioxole (215 mg, 1.21 mmol) in dichloromethane (1 ml) was added in one portion. The mixture was stirred at room temperature for 1 hour and then purified by column chromatography using silicon dioxide gel, eluting with methanol to afford the title compound (275 mg, 66 % yield): NMR (400 MHz, Chloroform-;/) delta 7.21 (q, 1H), 6.87 – 6.73 (m, 2H), 6.73 – 6.59 (m, 3H), 5.92 (s, 2H), 4.57 (t, 1H), 4.40 (s, 2H), 4.29 (d, 2H), 4.26 (m, 1H), 2.88 (d, 2H), 2.27 (s, 3H), 2.07 (m, 2H), 1.75- 1.60 (m, 4H); LC-MS : 418.2 [M+H]+.

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-(Methylenedioxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
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Application of 60702-69-4,Some common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

(Step 3) To a solution of the compound obtained in Step 2 (500 mg, 1.54 mmol) and 2-chloro-4-fluorobenzonitrile (240 mg, 1.54 mmol) in THF (15 mL) was added potassium t-butoxide (432 mg, 3.85 mmol) at room temperature, and the mixture was stirred for 14 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 75% ethyl acetate/hexane) to give the title compound (458 mg, 0.996 mmol, 64.6%) as a colorless powder. 1H-NMR (300MHz,DMSO-d6):delta1.03 (3H,d,J=6.0Hz), 1. 20-1.42(3H,m), 1.56-1.79(1H,m), 1.79-2.00(1H,m), 2.14-2.33(2H,m), 2.33-2.48(1H,m), 4.04-4.31(2H,m), 4.41(2H,q,J=6.9Hz), 7.00-7.26(2H,m), 7.35(1H,d,J=2.3Hz), 7.38-7.49(1H,m), 7.49-7.66(3H,m), 7.85(1H,d,J=8.7Hz), 8.04(1H,d,J=7.9Hz), 8.40(1H,s), 9.91(1H,s).

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (2014); A1;,
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Related Products of 499983-13-0, 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. 499983-13-0 name is 4-Bromo-3-fluorophenylacetonitrile, 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.

A solution of 2-(4-bromo-3-fluorophenyl)acetonitrile (0.78 g, 3.64 mmol) in H2SO4 (5 mL) and H2O (5 mL) was stirred at 100 C. for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was dissolved in H2O (20 mL) and extracted by EA (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a white solid of 2-(4-bromo-3-fluorophenyl)acetic acid (0.7 g, 2.046 mmol, 56.1% yield): 1H NMR (400 MHz, CD3OD) delta 7.53 (t, J=7.8 Hz, 1H), 7.16 (dd, J=9.8, 1.9 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 3.61 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-fluorophenylacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; EIDAM, Hilary Schenck; Raha, Kaushik; Gong, Zhen; Guan, Huiping; Wu, Chengde; Yang, Haiying; Yu, Haiyu; Zhang, Zhiliu; CHEUNG, Mui; US2014/275111; (2014); A1;,
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Electric Literature of 10406-24-3, 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. 10406-24-3, name is 3-(Aminomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 12; By removing ammonia by evaporation from the second hydrogenation product solution discharged from the outlet of the reaction tube B which was obtained in Example 2, a crude xylylenediamine containing 92.1% by weight of m-xylylenediamine and 520 ppm by weight of 3-cyanobenzylamine was obtained. In a SUS reaction tube having an inner diameter of 35 mm, 50 mL of a nickel/diatomaceous earth catalyst with a column shape having a diameter of 5 mm and a length of 5 mm (nickel content: 50% by weight) was packed. The catalyst was reduced for activation at 200 C. under hydrogen gas flow. After cooling, hydrogen gas was introduced under pressure into the reaction tube. The pressure was kept constant at 4 MPa, and the catalyst layer temperature was kept at 100 C. under external heating. Then, hydrogen gas was supplied from the inlet of the reaction tube at a flow rate of 1.1 NL/h. While keeping the flow of hydrogen gas, the above crude xylylenediamine was supplied from the inlet of the reaction tube in a rate of 25.2 g/h, to conduct the re-hydrogenation continuously. The hydrogenation product solution and unreacted hydrogen gas were discharged from the outlet of the reaction tube. The discharged hydrogenation product solution was sampled and analyzed by a gas chromatography. The concentration of m-xylylenediamine was 91.7% by weight and the concentration of 3-cyanobenzylamine was less than the detection limit of 30 ppm by weight. After evaporating off liquid ammonia from the obtained hydrogenation product solution, the crude m-xylylenediamine was distilled under reduced pressure (125 C., 6 Torr). The concentration of m-xylylenediamine was 99.99% by weight and the concentration of 3-cyanobenzylamine was less than the detection limit of 30 ppm by weight. As described above, in the method of the present invention, the amount of the solvent containing liquid ammonia to be used is reduced while keeping high yields even when using a simple apparatus, to reduce the quantity of energy required for removing the solvent. Therefore, the present invention provides a cost-effective method of producing xylylenediamines by the hydrogenation of phthalonitriles. Thus, the present invention is of a great industrial value.

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-(Aminomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kumano, Tatsuyuki; Shigematsu, Ryusuke; Kato, Kinji; Nakaya, Kenji; US2008/9654; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, COA of Formula: C9H6BrNO

Example 36 Preparation of 3-(4-bromophenyl)-3-hydroxypropanenitrile A suspension of 4-bromobenzoylacetonitrile (500 mg) in ethanol (5 mL) and acetic acid (300 muL) was heated with sodium cyanoborohydride (280 mg) using an 80 C. hot plate for 2 hours. After cooling to ambient temperature, the mixture was diluted with water and concentrated to a syrup, which was diluted with ethyl acetate and washed with water, sat. NaHCO3, and brine. The extract was dried with mgSO4, filtered, and evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane to provide the product (496 mg) as a thick oil.

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; ProLynx LLC; Santi, Daniel V.; Ashley, Gary W.; (80 pag.)US9387254; (2016); B2;,
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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 57381-51-8 as follows. Recommanded Product: 57381-51-8

Example 19: Scheme G2; Potassium tert-butoxide (2.1 equiv., 13.5 mmol, 1.51 g) was added to a stirred solution of 4-chloro-2-fluorobenzonitrile (G2.1) (1 equiv., 6.43 mmol, 1.0 g) and 3-amino-6- chloropyridine (1 equiv., 6.43 mmol, 0.826 g) in DMSO (3 ml). The reaction mixture was stirred at room temperature for 0.5 h. Water was added, the resulting precipitate was filtered off and washed successively with water, isopropanol and isopropyl ether to give G2.2 (1.17 g, yield = 69%).

According to the analysis of related databases, 57381-51-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2008/37784; (2008); A1;,
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Nitriles – Chemistry LibreTexts

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. 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 133541-45-4

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173 g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-1,1,1-trifluoropropanol [CAS 3539-97-7] dropwise (52.4 g, 460 mmol). The resulting mixture was heated at 70 C. for for 15 hours and cooled to room temperature. The reaction was concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3×). The combined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to give the desired product as a white solid (90.3 g, 93% purity, 64% yield). (0224) LC-MS (Method A): Rt=1.29 min; MS (ESIpos): m/z=312.0 [M+H]+. (0225) 1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83), 4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

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 Pharma Aktiengesellschaft; The Broad Institute, Inc.; Janzer, Andreas; Ferrara, Steven James; (19 pag.)US2019/307728; (2019); A1;,
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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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H6F3N

General procedure: To a solution of 10 (1.0 mmol, 1.0 equiv.) and substituted benzyl cyanate (1.2 mmol, 1.2 equiv.)in 5 mL of anhydrous DMF was added NaH 60% in mineral oil (66 mg, 2.0 mmol, 2.0 equiv.) at0C. The reaction mixture was allowed to warm to room temperature overnight, and was quenchedwith saturated NH4Cl and extracted with ethyl acetate (3 x 30 mL). The combined organic phaseswere washed with brine, dried over anhydrous MgSO4, filtered and concentrated to yield the crudeproduct. The product was purified via combi-flash on silica gel using 20% EtOAc in hexanes togive the desired product.

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:
Article; Tang, Jing; Do, Ha T.; Huber, Andrew D.; Casey, Mary C.; Kirby, Karen A.; Wilson, Daniel J.; Kankanala, Jayakanth; Parniak, Michael A.; Sarafianos, Stefan G.; Wang, Zhengqiang; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 390 – 399;,
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