Month: June 2021

Application of 228421-83-8, These common heterocyclic compound, 228421-83-8, name is 3,5-Difluoro-4-(hydroxymethyl)benzonitrile, 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.

To an ice-cold solution of 3,5-difluoro-4-(hydroxymethyl)benzonitrile (250 mg; 1.48 mmol) [CAS 228421-83-8] in dichlormethane (10 mL) was added phosphorus tribromide (0.07 mL; 0.74 mmol). The mixture was stirred at 0 C for 3 hours. The mixture was deactivated by water and diluted with dichloromethane (10 mL). The mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous Na2S04, filtered and concentrated to dryness to afford 4- (bromomethyl)-3,5-difluoro-benzonitrile (187 mg) as a white solid. ‘H-NMR (400 MHz, CDC13) delta ppm: 7.27 (s, 1H), 7.25 (s, 1H), 4.50 (s, 2H).

Statistics shows that 3,5-Difluoro-4-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 228421-83-8.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 939-80-0, These common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, 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.

General procedure: A mixture of benzenesulfonamides (1, 1.0 mmol), halogenated nitrobenzene(2, 1.0 mmol) and K2CO3 (1.1 mmol) were dissolved in DMF in a microwave tube. Then, the reaction mixture was irradiated in a microwave apparatus at 140 C for 12 minutes. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by column chromatography on silica gel to the desired products 3.

Statistics shows that 4-Chloro-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 939-80-0.

Reference:
Article; Huang, Zhi-You; Liu, Min; Mao, Yi-Jun; Chen, Yu-De; Wang, Yan-Ping; Liu, Chong; Tetrahedron Letters; vol. 60; 8; (2019); p. 626 – 629;,
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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 194853-86-6

Weigh 508mg of 5,5-dimethylhydantoin into eggplant-shaped bottles,Add 5mL DMF with stirring to completely dissolve it.Then add 220mg of K2CO3 (1eq) and stir at 45 C for half an hour.Make them fully mixed, and finally slowly add 4-fluoro-2-trifluoromethylbenzonitrile (300mg) in DMF and stir under heating for 5h. After the reaction is complete, cool to room temperature, add 30mL of ethyl acetate and dilute with 20 mL of saturated ammonium chloride aqueous solution was extracted three times, and saturated brine was extracted once. The organic layer was dried over anhydrous magnesium sulfate for 6 h, filtered with suction, and concentrated. Finally, 200-300 mesh column chromatography was performed to obtain 330 mg of a white solid. Yield 79%.

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhengzhou University; Xu Xia; Liu Hongmin; Ke Yu; Liang Jianjia; Xie Hang; (19 pag.)CN110790750; (2020); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1246213-27-3,Some common heterocyclic compound, 1246213-27-3, name is 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile, molecular formula is C21H25NO, 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.

Pd(OH)2/C (2.0 g) and compound 7 (20.0 g, 0.104 mol) were stirred in MeOH (150 mL) at room temperature under hydrogen at 10 psi pressure for 16-18 hours. The mixture was then filtered through a pad of Celite, and the filtrate was concentrated to give compound 15, which was used in the next reaction without further purification. 1H NMR (DMSO-d6; 400 MHz) delta 9.83 (s), delta 7.24 (s), delta 7.18 (m), delta 6.80 (m), delta 1.71 (s), delta 1.24 (s).

The synthetic route of 1246213-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; YANG, Xiaoqing; HADIDA RUAH, Sara, S.; GROOTENHUIS, Peter, D.J.; VAN GOOR, Fredrick, F.; BOTFIELD, Martyn, C.; ZLOKARNIK, Gregor; WO2010/108155; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 3598-13-8,Some common heterocyclic compound, 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, molecular formula is C8H6ClNO, 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. (5-Amino-2-chloro-4-pyridyl) acetonitrile To a stirred solution of potassium t-butoxide (24.69 g, 220 mmol, 2.2 eq) in anhydrous tetrahydrofuran (150 ml) at -50 C. under nitrogen, a solution of 2-chloro-5-nitropyridine (15.85 g, 100 mmol) and (4-chlorophenoxy)acetonitrile (E. Grochowski et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim., 11, 443 (1963)) (18.44 g, 110 mmol, 1.1 eq) in anhydrous tetrahydrofuran (150 ml) was added dropwise at such a rate that the reaction temperature was maintained at -40 to -50 C. with cooling in a dry ice/acetone bath. The resultant purple colored reaction mixture was then stirred at -78 C. under nitrogen for 1 hour, at which time glacial acetic acid (20 ml, 0.35 mol, 3.5 eq) was added to the reaction, and the mixture was allowed to warm to room temperature. A solution of 5% HCl (100 ml) was added to the reaction mixture and this aqueous mixture was extracted with ethyl ether (100 ml) and then with methylene chloride (2*100 ml). The extracts were combined, dried over magnesium sulfate, and passed through a silica gel filter (approximately 150 g) followed by methylene chloride (1200 ml). This filtrate was evaporated under reduced pressure, and the residual oil was chromatographed using silica gel (approximately 300 g) and eluted with 25% hexanes in methylene chloride to afford an oil (Rf =0.52 in methylene chloride) which was triturated in cold anhydrous ether to afford 6-chloro-3-nitro-2-pyridyl acetonitrile (1.37 g, 7%) as a white crystalline solid: mp, 121.5-123.5 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Chlorophenoxy)acetonitrile, its application will become more common.

Reference:
Patent; Pfizer Inc; US5811432; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-bromo-5-fluorobenzonitrile (CXII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HC1 (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CXIII) (24.0 g, 117.62 mmol, 53.5% yield). NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, 1H), 7.12 (d, J=8Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN mlz 203.9 (Br79M+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-Bromo-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (299 pag.)WO2017/24015; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 114772-53-1, 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. 114772-53-1, name is 4′-Methyl-[1,1′-biphenyl]-2-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A jacketed 1,000 mL 3-neck flask was charged with 4′-methylbiphenyl-2-carbonitrile (Compound 1, 100.0 g) and CH2Cl2 (500 mL) under nitrogen. To a 500 mL Erlenmeyer flask with magnetic stirrer, sodium bromate (NaBrO3; 31.2 g) was dissolved in water (170 mL). The NaBrO3 solution was transferred to the 1,000 mL flask and the reaction mixture was cooled to about 5 C. or less. Aqueous HBr solution (48%, 105.0 g) was added to the 1,000 mL flask and the resulting reaction mixture was recycled though a UV lamp reactor. The reaction mixture was kept at 0-20 C. and the recycling was continued until the reaction was deemed complete by HPLC. Optionally, additional sodium bromate and hydrogen bromide may be added. The relative amounts of Compound 2 and Compound 3 were about 80-90% and about 10-20% respectively. Aqueous sodium metabisulfite solution (2.0 g of in 10 mL water) was added to the reaction mixture. Allow the phases to settle and the methylene chloride phase was washed with water and used in the next step without further purification.

The synthetic route of 4′-Methyl-[1,1′-biphenyl]-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miranda, Edgar I.; Vlaar, Cornelis; Zhu, Jingyang; US2006/41147; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 79463-77-7, 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6.6. Example 6(S)-N-(3-chlorophenyl)-N’-cyano-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide A. Preparation of phenyl N-3-chlorophenyl-N’-cyanocarbamimidate. Diphenyl-N-cyanocarbonimidate (2 g, 8.4 mmol) and 3-chloroaniline (0.88 ml, 8.4 mmol) were added to acetonitrile (20 ml). The solution was heated at 50 C. overnight and cooled to room temperature, resulting in precipitation of the product. The white crystalline solid was filtered to give phenyl N-3-chlorophenyl-N’-cyanocarbamimidate (2 g, 7.3 mmol, 88%).1H NMR (400 MHz, chloroform-d) delta ppm 7.42-7.48 (m, 3H), 7.28-7.36 (m, 2H), 7.24-7.27 (m, 2H), 7.13-7.18 (m, 2H); MS (ES+) [M+H]+=272.

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Harrison, Bryce Alden; Kimball, Spencer David; Mabon, Ross; Rawlins, David Brent; Rice, Dennis S.; Voronkov, Michael Victor; Zhang, Yulian; US2009/42893; (2009); 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. 110301-23-0, name is 4-Amino-3,5-difluorobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H4F2N2

Step 4 4 g of sodium nitride was added to 30 ml of concentrated sulfuric acid and chilled to a temperature of 10 C. and 38 ml of acetic acid was added thereto. 8.9 ml of 4-cyano-2,6-difluoroaniline was added gradually to maintain the solution at a temperature of 20 to 25 C. The reaction mixture was added dropwise to a solution a 10 g of copper (I) bromide dissolved in 30 ml of concentrated hydrobromic acid. After the dropwise addition was completed, the reaction mixture was stirred for one and one half hours at room temperature. Water was added to the reaction mixture, the reaction mixture was extracted with chloroform and washed with water. The organic layer was removed by distillation, and the residue was recrystallized with a mixture of methanol and acetone to yield 6.6 g of 2-bromo-5-cyano-1,3-difluorobenzene.

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; Seiko Epson Corporation; US4883609; (1989); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, 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. SDS of cas: 50594-78-0

To a slurry of NaH (16 mg, 0.667 mmol) in THF (3.0 mL) were added 5-fluoro-2- nitrobenzonitrile (100 mg, 0.602 mmol) and phenol (57 mg, 0.606 mmol). The reaction vial was capped and the reaction mixture was stirred at RT for 50 min. Water (3 mL) and EtOAc (5 mL) were added. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 3 rnL). The combined organic layers were washed with brine (3 rnL) and then concentrated under a stream of nitrogen at 50 0C to afford the title compound (173 mg, 63%). LC-MS m/z 241 (M+H)+, 1.08 min (ret time).

The synthetic route of 5-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BULLION, Ann, Marie; BUSCH-PETERSEN, Jakob; EVANS, Brian; NEIPP, Christopher, E.; MCCLELAND, Brent, W.; NEVINS, Neysa; WALL, Michael, D.; WO2011/25799; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts