Month: May 2021

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. 766-84-7, name is 3-Chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Chlorobenzonitrile

General procedure: A 5 mL reaction tube was charged with Phen-MCM-41-CuBr (36 mg, 0.025 mmol), 2-aminopyridine 1 (0.6 mmol), nitrile 2 (0.5 mmol), ZnI2 (16 mg, 0.05 mmol), and 1,2-dichlorobenzene (1.5 mL) under an air atmosphere. The reaction tube was sealed and placed in an oil bath at r.t. The reaction mixture was stirred at 130 C for 24 h. After cooling to r.t., the reaction mixture was diluted with EtOAc (10 mL) and filtered. The supported copper catalyst was washed with water (2 5 mL) and acetone (2 5 mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (hexane/EtOAc, 3:2) to provide the desired product 3.

The synthetic route of 766-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xia, Jianhui; Huang, Xue; Cai, Mingzhong; Synthesis; vol. 51; 9; (2019); p. 2014 – 2022;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. Safety of 4-Cyano-3-trifluoromethylaniline

4-cyano-3-trifluoromethyl-aniline is reacted with itaconic anhydride (66) to yield intermediate 67. Further epoxidation and opening of the epoxide ring with p-CN-phenol 50 yields compound XLVI as presented in Figure IG.

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

Reference:
Patent; OSURF (OHIO STATE UNIVERSITY RESEARCH FOUNDATION); UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; WO2008/11072; (2008); A2;,
Nitrile – Wikipedia,
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. 14447-18-8, name is Benzyl cyanoacetate, A new synthetic method of this compound is introduced below., Product Details of 14447-18-8

The reactor is addedCyanoacetic acid benzyl ester 63 mL (0.5 mol)1-butyl-3- methyl imidazole trifluoroacetate126mL,N-octadecyl-3-aminoacrolein19 mL (0.1 mol) was homogeneously mixed,The oil bath was heated to a temperature of 90 C and incubated for 4 h to carry out the reaction,TLC detection (petroleum ether: dichloromethane 1: 2 development, sublimation iodine color) N-octadecyl-3-aminopropenal reaction completely, cooled to room temperature, organic solvent1,2-dichloroethane 60mL extraction 3 times, residual phase ion water washing vacuum drying and reuse,The organic phase was passed into the HCl gas and the reaction was followed by HPLC until the reaction was complete. Add concentrated ammonia to adjust the pH = 5-6, liquid separation, water use1,2-dichloroethane 20 mL x 3 times extraction,The organic layers were combined, washed with water and separated, and the solvent was distilled off under reduced pressure to give 1,2-dichloroethane2-chloronicotinic acid benzyl ester, pale yellow liquid 23.7g, the yield was 95.5%.

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; Shandong Normal University; Liu Yufa; Mao Feifei; Zhang Hongtao; Kan Baohong; Sun Lin; Chen Dongmei; Qian Xiaoping; (11 pag.)CN105001154; (2017); B;,
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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Bromo-4-fluorobenzonitrile

To a mixture of 15 (0.100 g, 0.43 mmol) and NaH (15.5 mg, 0.65 mmol) in DMF (8 mL) was added 2-bromo-4-fluorobenzonitrile (86 mg, 0.43 mmol) and heated at 90 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue chromatographed (hexane/EtOAc, 10:1-10:2) to give 0.162 g (91%) of 16 as a white solid. 1H NMR (CDCl3) delta 7.97 (d, J = 2.1 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 (dd, J = 8.4, 2.1 Hz, 1H), 2.89 (s, 2H), 2.51 (s, 2H), 1.16 (s, 6H); MS (ESI): m/z 410.0/412.0 [M-H]-.

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 36282-26-5.

Reference:
Article; Taldone, Tony; Zatorska, Danuta; Patel, Pallav D.; Zong, Hongliang; Rodina, Anna; Ahn, James H.; Moulick, Kamalika; Guzman, Monica L.; Chiosis, Gabriela; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2603 – 2614;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile, 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 145689-34-5, Quality Control of 2-(2,3-Difluorophenyl)acetonitrile

Step 5: A stirred solution of 4-(5-difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzaldehyde (40.5 mg, 0.13 mmol) and 2,3-difluorobenzylacetonitrile (20.3 mg, 0.13 mmol) in Ethanol (1 mL) was treated with 40% aqueous KOH (0.1 mL) at room temperature. The mixture was stirred for 1 hour. The resultant white precipitate was collected by filtration and washed with water to provide 5-difluoromethoxy-1-{4-[2-(2,3-difluoro-phenyl)-2-isocyano-vinyl]-phenyl}-3-trifluoromethyl-1H-pyrazole (30 mg, 51% yield) as a white solid: 1H-NMR (CDCl3) delta 6.39 (s, 1H), 6.62 (t, 1H, J=70.8 Hz), 7.14-7.28 (m, 2H), 7.36-7.42 (m, 1H), 7.65 (s, 1H), 7.80 (d, 2H, J=8.7), 8.02 (d,2H,J=8.7) ppm. ESMS calculated for C20H10F7N3O: 441.1; Found: 442.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,3-Difluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Chen, Shoujun; Ying, Weiwen; Jiang, Jun; Ono, Mitsunori; Sun, Lijun; US2005/272699; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 50594-78-0,Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 2: 5-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile 5-Fluoro-2-nitrobenzenecarbonitrile (1.02 equivalents) and N-methylpiperazine (1.0 equivalents) were dissolved in NMP. Triethylamine (2.1 equivalents) was added, and the resulting solution heated at 100 C. for 1 hour. The solution was cooled to room temperature and poured into H2O. A precipitate formed which was filtered to yield the desired product as a green solid. LC/MS m/z 247.3 (MH+), Rt 1.46 minutes.

The synthetic route of 50594-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; US2005/256157; (2005); A1;; ; Patent; Chiron Corporation; US2005/261307; (2005); A1;,
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 868-54-2 as follows. Application In Synthesis of 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: A mixtureof 1 mmol of the corresponding aromatic aldehyde, 0.132 g (1 mmol) of malononitrile dimer, 0.125 g (0.2 mmol) of Triton X-100, and one drop of triethylamine in 5 mL of water was stirred at room temperature until the reaction was complete (TLC). The precipitate was ground with water, filtered off, washed with water, and recrystallized from propan-2-ol.

According to the analysis of related databases, 868-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ershov; Bardasov; Alekseeva, A. Yu.; Ievlev, M. Yu.; Belikov, M. Yu.; Russian Journal of Organic Chemistry; vol. 53; 7; (2017); p. 1025 – 1029; Zh. Org. Khim.; vol. 53; 7; (2017); p. 1014 – 1018,5;,
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 935-02-4 as follows. Computed Properties of C9H5N

The mixture of phenol (0.1 g, 1.1 mmol), 3-phenylpropiolonitrile (0.13 g, 1.0 mmol), sodium carbonate (0.11 g, 1.0 mmol) in DMF (2 mL) was stirred at room temperature for 12 h. The reaction was monitored by TLC. After the completion of the reaction, the mixture was extracted with ethyl acetate (3×10 mL), and the liquor was washed with saturated brine (3×10 mL). The resulting organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give product (0.22 g, 99% ). (Z)-3-Phenoxy-3-phenylacrylonitrile (3a)5 Colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.47 (d, J = 7.0 Hz, 2H), 7.34 (d, J = 7.2 Hz, 1H), 7.29 (d, J = 7.8 Hz, 2H), 7.23 – 7.18 (m, 2H), 7.01 (t, J = 7.4 Hz, 1H), 6.93 (d, J = 7.8 Hz, 2H), 5.32 (s, 1H). 13C NMR (150 MHz, CDCl3) delta 168.43, 155.72, 131.47, 129.75, 128.93, 126.92, 124.24, 118.16, 115.32, 115.09, 81.83. Anal. Calcd. for C15H11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 81.49; H, 4.99; N, 6.30.

According to the analysis of related databases, 935-02-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Du, Yan; Li, Zheng; Tetrahedron Letters; vol. 59; 52; (2018); p. 4622 – 4625;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 13338-63-1, A common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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 1: Under a nitrogen atmosphere, in a glove box, Add 0.02 mmol of Pd2(dba)3·HCCl3 (tris(dibenzylideneacetone)dipalladium·chloroform), 0.04 mmol of tBuDavePhos. (2-di-tert-butylphosphonium-2-(N,N-dimethylamino)biphenyl) or 2-di-tert-butylphosphine-2′-(N,N-dimethylamino)-1,1′-biphenyl, 0.52 mmol of diphenylphosphine oxide, 1.5 equivalents of t-BuOK (potassium tert-butoxide), Adding to the Schlenk reaction tube in turn, then adding 0.4 mmol of 3,4,5-trimethoxybenzyl nitrile compound, vacuuming and backfilling with nitrogen; Under a nitrogen atmosphere, a solvent of 3 ml of 1,4-dioxane was added, and the reaction was continued at 120 C for 16 h. After the reaction is completed, it is cooled to room temperature and separated by column chromatography. The target product was obtained: 3,4,5-trimethoxybenzyldiphenylphosphine oxide in a yield of 96%.

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; Hunan University; Zhang Jishu; Qi Tafamingrenqingqiubugongkaixingming; (13 pag.)CN109438512; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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. Product Details of 67515-59-7

A solution of 1.1 g (5.9 mmol) of 4-fluoro-3- trifluoromethylbenzonitrile and 485 mg (6.5 mmol) of [(S)- (+)-2-BUTANOL] in 10 mL of THE at-10 C was treated with 235 mg (5.9 mmol) of sodium hydride. The resulting mixture was stirred cold for 2 h, then quenched with 10 mL of [H2O.] The quenched solution was extracted with 30 mL [OF ET20,] dried over [MGS04] and concentrated. Chromatography on a Biotage 40M cartridge using 4: 1 v/v hexanes/EtOAc as the eluant afforded 550 mg of the title compound [: 1H] NMR (500 Mhz) [5] 0.99 (t, J=7.6, 3H), 1.35 (d, J=6.2, 3H), 1.58-1. 83 (m, 2H), 4.51 (septet, 1H), 7.04 (d, J=8.7, 1H), 7.75 (d, J=8.7, 1H), 7.85 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67515-59-7, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; WO2003/105771; (2003); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts