Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 501-00-8, name is 2-(3-Fluorophenyl)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 501-00-8, Quality Control of 2-(3-Fluorophenyl)acetonitrile

General procedure: To a solution of 11a-c (10 mmol) in anhydrous DMF (15 mL) was added appropriate aryl acetonitriles (12 mmol). After stirring at -10C for about 15 min, 60% NaH (0.48 g, 12 mmol) was added portion wise under a nitrogen atmosphere and maintained at this condition for 1 h. Then, the resulting mixture was warmed slowly to room temperature and continued to react for 12-24 h. After that, additional NaH (0.48 g, 12 mmol) was added and the air was introduced, the mixture was stirred at room temperature for another 12-24 h to yield 13a-q. Without further purification, 13a-q were hydrolyzed with 30% aqueous sodium hydroxide at room temperature for 4 h, and afterwards, the mixture was poured into 300 ml H2O and neutralized with 3N HCl. The precipitate was collected and purified by column chromatography on silica gel (hexane: EtOAc=8:1-1:1) to afford the target compounds 7a-q.

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; Wu, Hai-Qiu; Yan, Zi-Hong; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6477 – 6483;,
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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 10406-25-4

Example 7 p-Cyanobenzylamine (13.2 g), water (18 g), and methylene chloride (18 g) were mixed, and the mixture was stirred with cooling with ice. Acetic acid (18 g) was added to the mixture. Subsequently, a 20 wt % aqueous solution (51.8 g) of sodium nitrite was added dropwise to the mixture over a one hour period. The mixture was stirred at the same temperature for four hours. The reaction mixture was subjected to extraction with methylene chloride, and the organic solvent was concentrated. Water was added to the concentrated solution, and the residual organic solvent was removed through distillation, to thereby obtain 14.7 g of p-cyanobenzyl acetate (yield 84%). The purity of the product was 98%.

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; Showa Denko K.K.; US6187945; (2001); B1;,
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. 119584-73-5, name is 2-Ethoxy-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8FNO

b) 4-Ethoxybenzo[d]isoxazol-3-amine I53 To a solution of acetohydroxamic acid (2.18 g, 29 mmol) in DMF (40 ml.) at 0 C under N2was added t-BuOK (3.26 g, 29 mmol) and the mixture was stirred at RT for 1 h. 2-Ethoxy-6-fluorobenzonitrile I52 (1.6 g, 9.7 mmol) was then added and the mixture was stirred at RT overnight. The mixture was diluted with DCM (80 ml_), washed with water (60 ml. x 4), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet.ether/EtOAc = 5/1) to give the title compound (240 mg, 15%) as a white solid. LCMS- E: Rt5.05 min; m/z 179.0 [M+H]+.

According to the analysis of related databases, 119584-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 447-60-9,Some common heterocyclic compound, 447-60-9, name is 2-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

45.3 ml of a 1.8 M lithium diisopropylamide THF solution (81.6 mmol) was diluted with 68 ml of THF. Thereafter, 28 ml of a THF solution containing 5.0 g (27.2 mmol) of the 5-chloro-2,N-dimethylbenzamide prepared in Step A was added dropwise to the diluted solution at -78C. Thereafter, 28 ml of a THF solution containing 4.65 g (27.2 mmol) of 2-trifluoromethylbenzonitrile was further added thereto, and the obtained mixture was then stirred at -78C for 2.5 hours. The temperature of the reaction solution was increased to a room temperature, and a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, a solid generated as a result of vacuum concentration was filtrated, so as to obtain 6.87 g (78%) of 7-chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless solid. 1H-NMR (270MHz, CDCl3) delta (ppm): 6.49 (1H, s), 7.33-7.72 (5H, m), 7.81-7.84 (1H, d, J=7.26Hz), 8.32-8.33 (1H, d, J=1.65Hz), 9.18 (1H, brs) ESI (LC-MS positive mode) m/z 324 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1724262; (2006); A1;,
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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5414-21-1

General procedure: A stainless steel autoclave was charged with glycerol (1 mmol), base B (6 mmol), and NMP (1mL), flushed three times with CO2, and finally charged with CO2 to 0.7 MPa at room temperature.The obtained mixture was magnetically stirred at 25 C for 1 h, and an alkyl halide (10 mmol) wasadded at room temperature after CO2 evacuation, followed by repeated CO2 flushing/charging to 0.7MPa. The reaction mixture was magnetically stirred at 25 C for 18 h under 0.7 MPa pressure ofCO2. After EtOAc was added to the resulting mixture to precipitate the dissolved salt, the salt wasremoved using a Buchner funnel and washed with EtOAc. The combined filtrate was concentrated in vacuo, and the obtained product ratios were determined by 1H NMR measurements. The crudeproduct was purified by silica gel column chromatography, affording linear tricarbonates 1.Compounds 1g, 1h, and 1k were further purified by gel permeation liquid chromatography.

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; Mihara, Masatoshi; Moroga, Kaname; Iwasawa, Tetsuo; Nakai, Takeo; Ito, Takatoshi; Ohno, Toshinobu; Mizuno, Takumi; Synlett; vol. 29; 13; (2018); p. 1759 – 1764;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 32703-82-5, name is 6-(tert-Butyl)naphthalene-2,3-dicarbonitrile, 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 32703-82-5, HPLC of Formula: C16H14N2

A mixture of 6-tert-butyl-2,3-dicyanonaphthalene A (18.8 g, 0.08 mol), anhydrous zinc acetate B (3.7 g, 0.02 mol), dry quinoline 100 mL and DBU 12 mL was stirred at 180 deg C for 20 hr. After cooling, the mixture was poured into methanol (3500 mL). The crude product was collected by vacuum filtration, washed with methanol and purified by Soxhlet extraction with methanol for 2 days. Finally, the dark green residue was chromatographed on silica gel with chloroform as the eluting solvent. Chloroform was evaporated and product triturated with methanol, again collected by filtration and vacuum dried at 70 deg C. Yield was 9 g or 45% of theoretical.

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, 6-(tert-Butyl)naphthalene-2,3-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EASTMAN KODAK COMPANY; WIDZINSKI, Thomas, J.; PAWLIK, Thomas, D.; OLM, Myra, Toffolon; BOSE, Judith, A.; WO2013/55640; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 20249-16-5, These common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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.

into a 500-mL round-bottom flask, was placed a solution of 3-oxocyclobutane-l-carbonitrile (4 g, 42.06 mmol, 1.00 eq.) tetra(propan-2-yloxy)titanium (14.16 g, 62.90 mmol, 1.50 eq.) and 2- methylpropane-2-sulfinamide (6.12 g, 50.49 mmol, 1.20 eq.) in tetrahydrofuran (200 mL). The resulting solution was stirred for 16 hours at 65C. The reaction was cooled to 25C. Then NaBH4 (3.2 g, 84.60 mmol, 2.00 eq.) was added. The mixture was stirred for 2 hours at 25C. The reaction was then quenched by the addition of 200 mL of water. The solids were filtered out and the resulting solution was extracted with ethyl acetate (2×200 mL) and the organic layers were combined. The resulting mixture was washed with brine (2×300 mL), dried over sodium sulfate and concentrated under vacuum. This resulted in 7.2 g (85%) of N-(3- cyanocyclobutyl)-2-methylpropane-2-sulfinamide as a yellow solid.

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 67832-11-5, A common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, molecular formula is C8H6BrN, 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.

A. 4-Bromo-2-methylbenzamide. A solution of 4-bromo-2- methylbenzonitrile (1.0 g, 5.1 mmol), trifluoroacetic acid (4.0 mL) and sulfuric acid (1.0 mL) were combined and heated to 65 C for 18 h. The reaction was poured into ice water and the product precipitated and was collected by filtration. The resulting material was dried under vacuum overnight to afford the title compound as a white solid (0.96 g, 88%). MS (ESI) m/z 420.5 [M+ 1]+.

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 621-03-4, 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. 621-03-4 name is 2-Cyano-N-phenylacetamide, 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: Under N2 atmosphere, t-BuOK (246 mg, 2.2 mmol) and various acetamides 2 (1.0 mmol) in dry THF (5 mL) were placed in a 10 mL Schlenk flask at -78 C. The suspension was warmed to room temperature for 30 min and recooled to -78 C. (Z)-methyl-bromo-4,4,4-trifluorobut-2-enoate 1 (117 mg, 0.5 mmol) was added at this temperature. The solution was stirred at this temperature until the reaction was completed (usually 15-30 min), followed by adding saturated aqueous NH4Cl solution (10 mL). The solution mixture was extracted with EtOAc (3×10 mL), and the combined organic layer was washed with brine, then, dried over Na2SO4. After removal of solvents under vacuum, the crude product was further purified by silica gel column chromatography (PE:EA = 1:2 v/v) to afford pure product 4.

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

Reference:
Article; Zhang, Hong-Hai; Shen, Wei; Lu, Long; Tetrahedron Letters; vol. 59; 11; (2018); p. 1042 – 1045;,
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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 796600-15-2

Example 38; DL-Threo-2-chloro-4-(2-hydroxy-2-phenyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethylamino)-3-methylbenzonitrile; Intermediate 38a; DL-Threo-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxy-3-phenylpropanoic acid; 2-chloro-4-fluoro-3-methylbenzonitrile (2.0 g, 11.79 mmol) was mixed together with DL-Threo-3-phenylserine hydrate (2.82 g, 14.15 mmol) in DMSO (15 mL). K2CO3 (3.26 g) was added to the reaction mixture and stirred at 75 C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly into a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexanes/EtOAc and then with EtOAc, 100% to get the pure final product (800 mg). 1H NMR (500 MHz, acetone-d6, delta in ppm) 7.52 (m, 3H), 7.37 (d, J=9 Hz, 1H), 7.2-7.30 (m, 2H), 6.81 (d, J=9 Hz, 1H), 6.44 (d, J=6 Hz, 1H), 5.42 (m, 1H), 4.5 (br s, 1H), 4.17 (m, 1H) 2.24 (s, 3H)

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; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts