Month: November 2020

Adding a certain compound to certain chemical reactions, such as: 4640-66-8, name is 4-Chlorophenacylcyanide, 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 4640-66-8, 4640-66-8

Add Na2CO3 (0.25 mmol) to a 25 mL reaction flask,a compound (0.5 mmol) represented by the formula i1,a compound of formula m2 (0.5 mmol) and acetonitrile (3 mL),The reaction was carried out at 90 C for 24 h, and the reaction was followed by thin layer chromatography.After the reaction was completed, the solvent was evaporated under reduced pressure and ethyl acetate was dissolved.Separation on a silica gel column (developing solvent petroleum ether / ethyl acetate volume ratio = 6:1) afforded white solid compound A14.(The structural formula of the compound A14 is as shown by n3,The synthesis reaction formula is shown in Fig. 26, and the yield was 68%).

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, 4-Chlorophenacylcyanide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Normal University; Li Qianqian; He Xinwei; Tao Jiajia; Shang Yongjia; (26 pag.)CN108440467; (2018); A;,
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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 179898-34-1 as follows. 179898-34-1

Example 1; 3-fluoro-5-{5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridin-2-yl}benzonitrile; Step 1: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; 3-Bromo-5-fluorobenzonitrile (30.0 mmol, 9.23 g), bis(pinacolato)diboron (30.0 mmol, 7.62 g), PdCl2(dppf)2 (1:1 complex with dichloromethane, 1.2 mmol, 980 mg), and potassium acetate (105 mmol, 10.3 g) were combined in deoxygenated dioxane (150 mL) and heated at 80 C. for 4 hrs, at which time the reaction was determined to be complete by GC/MS analysis. The reaction was cooled to room temperature, and poured in to a separatory funnel containing EtOAc (300 mL) and water (200 mL). The aqueous layer was back extracted with EtOAc (75 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was carried on to the next step with out further purification or characterization.

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cosford, Nicholas D.; Seiders, Thomas J.; Payne, Joseph; Roppe, Jeffrey R.; Huang, Dehua; Smith, Nicholas D.; Poon, Steve F.; King, Chris; Eastman, Brian W.; Wang, Bowei; Arruda, Jeannie M.; Vernier, Jean-Michel; Zhao, Xiumin; US2009/203903; (2009); A1;,
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40497-11-8, 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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask. The prepared diazonium salt solution was dropped into the flask. The reaction was complete for 2 h. Adding aqueous ammonia, adjust the pH to 9-10. Reaction at room temperature for 2h. After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2 x 30 mL), washed with saturated sodium chloride solution (1 x 40 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1.60 g of product, yield 65.3%.

The synthetic route of Ethyl 2,3-dicyanopropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Guan, Xilin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (14 pag.)CN105601632; (2016); A;,
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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. 14618-78-1 name is 4,4-Dimethoxybutanenitrile, 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. 14618-78-1

In a 500 ml four-necked flask,Add 60 grams of DMF,13.0 g (0.1 mol) of 4,4-dimethoxy-n-butyronitrile,10.0 g (0.11 mol) of 2,3-difluoropropenal,0.8 g DBU, reacted at 80 C for 5 hours,The gas phase detection 1,4-addition reaction is completed.Cool down to 25-30 C,Add 10.0 grams of potassium carbonate,22.0 grams of 17% ammonia,10.0 g of ammonium chloride,Reaction at 80 C for 4 hours,Cool down to 20-25 C,filter,20 grams of ice water wash filter cake,dry,Obtained 11.4 g of 5-fluoro-7-azaindole,Liquid phase purity is 99.2%,The yield was 83.8%.

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

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Zhang Mingfeng; Wang Sheng; Li Guangqian; Ju Lizhu; (7 pag.)CN110128421; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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 591769-05-0, 591769-05-0

3.0g of compound 9 and 2.9g of compound 5a were dissolved in 150mL acetonitrile. To the above solution, 0.10g of 1,8-diazabicyclo undec-7-ene was added and reacted at 65¡ãC for 2 days. TLC was used to determine reaction completion. After distilling off the solvent, it was dissolved in ethyl acetate then water and aqueous citric acid solution was added. 100mL saturated sodium chloride solution was washed 3 times each. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by column chromatography (methylene chloride/methanol 80:1) to give 2.4g of intermediate 10a as a white solid, yield: 48percent.

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-Cyclopentylacrylonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

327056-73-5, These common heterocyclic compound, 327056-73-5, name is 3-Chloro-5-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.

3-chloro-5-(3-chloro-5-methoxyphenoxy)benzonitrile(B-3); A mixture of 1.00 g (6.31 mmol) of 3-chloro-5-methoxyphenol (B-1), of 1.28 g (8.20 mmol) 3-fluoro-5-chlorobenzonitrile (B-2), and 2.62 g (18.93 mmol) of potassium carbonate in 10 mL of N-methylpyrrolidinone was heated at 120 C. in a nitrogen atmosphere with vigorous stirring. After 6 hours, LC/MS analysis indicated that the reaction was complete. The reaction was cooled to room temperature and filtered, and the solid washed with EtOAc. The filtrate was diluted further with EtOAc, and was washed with 20 mL of 1N HCl, 20 mL of 1 N NaOH, 20 mL of water, and 20 mL of brine. The organic layer was dried (anhydrous MgSO4), filtered, and the filtrate concentrated in vacuo to an orange oil. The oil was purified by flash column chromatography over silica gel with 3:1 cloroform/hexanes to give the desired product B-3 as a clear oil. MS: M+1=295. 1H NMR(CDCl3): 3.81 delta(s, 3H), 6.44 m, 1H), 6.62 (m,1H), 6.78 (m,1H), 7.14 (m,1H), 7.22(m,1H), 7.37(m,1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 327056-73-5.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, 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. 179897-89-3

General procedure: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether). 4.1.1.1. 5-Bromo-2-(isobutyl(methyl)amino)-benzonitrile (2a).Yellow oil (yield: 93%); 1H NMR (400 MHz, CDCl3) d 7.54 (d, 1H,J 1.3 Hz, ArH), 7.42 (dd, 1H, J 9.1, 3.3 Hz, ArH), 6.75 (d, 1H,J 9.1 Hz, ArH), 3.19 (d, 2H, J 7.5 Hz, -NCH3CH2CH(CH3)2), 3.05 (s,3H, -NCH3CH2CH(CH3)2), 2.01 (m,1H, eNCH3CH2CH(CH3)2), 0.89 (d,6H, J 6.6 Hz, eNCH3CH2CH(CH3)2).

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

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
Nitrile – Wikipedia,
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10406-25-4, 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below.

Pyridin-3-ylmethanol (0.546 g, 5 mmol) in THF (2ml) was added to a suspension of 1 , 1 ‘-carbonyldiimidazole (0.81 1 g, 5.00 mmol) in THF (8ml) at 10 C. The mixture was stirred for 1 h at rt. The resultant solution was added to the solution of 4-(aminomethyl)benzonitrile (0.661 g, 5.00 mmol), DBU (0.754 ml_, 5.00 mmol), and Et3N (0.697 ml_, 5.00 mmol) in THF (10 ml). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure, and the residue was partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried over MgS04, filtered, and concentrated under reduced pressure. The residue was recrystallized in EtOAc/hexanes to afford the title compound as a white solid (0.85 g, 63%). 1H NMR (400 MHz, DMSO-d6) delta 8.62 (s, 1 H), 8.57 (d, J = 3.91 Hz, 1 H), 8.03 (t, J = 5.87 Hz, 1 H), 7.75 – 7.89 (m, 3H), 7.40 – 7.52 (m, 3H), 5.12 (s, 2H), 4.32 (d, J = 6.07 Hz, 2H). LCMS: fR = 0.44 min, 88%.. MS (ESI): m/z 268 (M+H)+.

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; GLAXOSMITHKLINE LLC; TEMPERO PHARMACEUTICALS, INC.; GHOSH, Shomir; LOBERA, Mercedes; TRUMP, Ryan, Paul; ZHANG, Cunyu; CHEN, Peiling; WO2013/66835; (2013); A2;,
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The chemical industry reduces the impact on the environment during synthesis 143879-80-5, name is 2,3,4-Trifluorobenzonitrile, I believe this compound will play a more active role in future production and life. 143879-80-5

0.32 cm3 of hydrazine monohydrate is added to 0.46 cm3 of 2,3,4-trifluorobenzonitrile in 10 cm3 of absolute ethanol. The medium is heated at about 75 C. for 17 hours and then 10 cm3 of ethyl acetate, 5 cm3 of tetrahydrofuran and 5 cm3 of distilled water are added. The organic phase is separated out after settling of the phases has taken place, and is washed again with 10 cm3 of distilled water and then with 10 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50 C.). The residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 mum; diameter 1.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume). The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa; 40 C.); after drying (90 Pa; 40 C.), 100 mg of 6,7-difluoro-1H-indazole-3-amine are obtained in the form of a white solid melting at 183 C. [0561] 1H NMR spectrum (300 MHz, (CD3)2SO-d6, delta in ppm): 5.57 (unresolved peak: 2H); 6.93 (mt: 1H); 7.52 (ddd, J=8.5-4.5 and 1 Hz: 1H); 12.01 (unresolved peak: 1H).

The chemical industry reduces the impact on the environment during synthesis 143879-80-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dutruc-Rosset, Gilles; Lesuisse, Dominique; Rooney, Thomas; Halley, Franck; US2004/14802; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

63069-50-1, Name is 4-Amino-3-fluorobenzonitrile, 63069-50-1, 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.

General procedure: To the solution of compound 15 (0.2 mmol) and 2-aminobenzonitrile (0.6 mmol) in n-BuOH (3 mL) was added DIPEA (0.6 mmol). After stirred at 90 C for 12 h, the reaction mixture was diluted with EtOAc, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the product 16 as yellow solid. (22 mg, 25%).

Statistics shows that 4-Amino-3-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 63069-50-1.

Reference:
Article; Fang, Yuanying; Yang, Zunhua; Gundeti, Shankariah; Lee, Jongkook; Park, Haeil; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 254 – 260;,
Nitrile – Wikipedia,
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