Month: June 2021

Electric Literature of 501-00-8, 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(3- fluorophenyl)acetonitrile (100 g, 0.74 mol) in Dry DMF (1000 ml) was added 1,5- dibromopentane (170 g, 0.74 mol), NaH (65 g, 2.2 eq) was added dropwise at ice bath. After addition, the resulting mixture was vigorously stirred overnight at 50C. The suspension was10 quenched by ice water carefully, extracted with ethyl acetate (3*500 ml). The combined organic solution was concentrate to afford the crude which was purified on flash column to give 1-(3-fluorophenyl)cyclohexanecarbonitrile as pale solid (100 g, 67%).

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF MODENA AND REGGIO EMILIA; COSENZA, Maria; POZZI, Samantha; (78 pag.)WO2016/87950; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 38487-86-4, A common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

[00393] Intermediate 34A. 2-Azido-4-chlorobenzonitrile: To a solution of 2-amino-4- chlorobenzonitrile (2.0 g, 13.11 mmol) in TFA (12 mL) was added water (2.4 mL). After cooling to 0 C, sodium nitrite (0.904 g, 13.11 mmol) was added over a period of 0.5 h. After this addition, sodium azide (2.164 g, 33.3 mmol) in water (5 mL) was gradually added dropwise. The reaction was stirred at 0 C for 10 min, and then allowed to warm to room temperature. After 2 h, quenched the reaction with water (100 mL) and insoluble solid was filtered and dried under suction and nitrogen. Aliquot LCMS analysis indicated starting material disappeared and a new peak formed which was not ionizing.

The synthetic route of 38487-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 15666-97-4,Some common heterocyclic compound, 15666-97-4, name is Octyl 2-cyanoacetate, molecular formula is C11H19NO2, 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.

In a 500 mL three-neck flask reactor equipped with a thermometer,32 mL (0.25 mol) of n-octyl cyanoacetate was added,Tetrabutyl ammonium bromide 10mL,3-Diethylamino acrolein62mL (0.5mol),Place the prepared device in the microwave.Set microwave radiation conditions, 40C temperature,Microwave power is 100W and frequency is 2450MHz.TLC test (petroleum ether:dichloromethane 1:2 development, sublimation iodine coloration) 3-diethylamino acrolein reaction is complete,Cool down to room temperatureHCl gas was passed through and the reaction was continued under microwave irradiation and the reaction was followed by HPLC until the reaction was complete.Add 5% potassium hydroxide solution to adjust the pH = 5-6, liquid separation, the aqueous layer was extracted with butyl acetate 20mL × 3 times,The organic layers are combined, washed after washing, and the molecular sieves are dried.After filtration and evaporation of the solvent, butyl acetate is recovered.An n-octyl 2-chloronicotinate was obtained, 61.3 g of a colorless liquid, with a yield of 92.4%. :

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

Reference:
Patent; Shandong Normal University; Liu Yufa; Li Dechao; Gu Qiaolian; Sun Lin; Xu Jun; Zhao Jianxia; Cheng Guiying; (11 pag.)CN104945316; (2018); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

Reaction in toluene between 2-acetoxy-2-methyl-3-(4-fluorophenylthio) propionic acid (intermediate ?acetylacid?) and thionyl chloride to give the intermediate 2-acetoxy-2-methyl-3-(4-fluorophenylthio) propionyl chloride (intermediate ?chloride?). The successive reaction of this intermediate (still in toluene) with 4-cyano-3-trifluoromethyl aniline (in the presence of 4-dimethylamino pyridine) to give N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-acetoxy-2-methyl-propionamide (intermediate ?acetylsulfide?). Evaporation of the toluene and use of the residual oil in the following step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Cyano-3-trifluoromethylaniline, its application will become more common.

Reference:
Patent; Pizzatti, Enrica; Vigano, Enrico; Lussana, Massimiliano; Landonio, Ernesto; US2006/41161; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3939-09-1, name is 2,4-Difluorobenzonitrile, 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 3939-09-1, Safety of 2,4-Difluorobenzonitrile

Anhydrous p-toluene sulfonic acid (25.0 g, 137.43 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (10 g, 55.25 mmol) obtained in step 1 of Preparation Example 1 and 2,4-difluorobenzonitrile (11.53 g, 82. 87 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (10.0 g, 31.22 mmol) in a yield of 57 %. 1H NMR (CDCl3): delta 8.31-8.22 (1H, m), 7.82-7.79 (1H, d), 7.65 (1H, s), 7.02-6.85 (3H, m), 3.88 (6H, s) MW: 320

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Oxocyclobutanecarbonitrile

Compound 10-2 (8.0g, 84.21mmol) was dissolved in DCM (80mL) at 0C, added DAST (27g, 0.168mol). The reaction mixture was stirred overnight at room temperature, and the end of the reaction was monitored by TLC (petroleum ether/ethyl acetate = 3: 1). Ice water was added to the reaction solution, extracted with DCM, washed with saturated brine, and then dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure and purified by column chromatography (petroleum ether/ethyl acetate = 150: 1-30:1) to give the crude Compound 10-3 (8.1g) as a brown oil.

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

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Hui; DONG, Yanyan; EP2738156; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 22364-68-7, name is 2-(o-Tolyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 22364-68-7

General procedure: Nitriles (1 mmol) were added to a solution of NaN3 (3 mmol), PhMe (50 mL), and Et3N.HCl (3 mmol) in around-bottomed flask. The reaction mixture was stirred at 110 C. After completion of the reaction (as indicated byTLC), the product was cooled and extracted with water. Next, 36% HCl was added dropwise to the aqueous layer to precipitate the tetrazoles. After filtration, the solid wasdried under reduced pressure and recrystallized fromEtOAc/Et2O to yield the 5-substituted-1-H-tetrazoles.

The synthetic route of 22364-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liao, Ai-Mei; Wang, Tiantian; Cai, Bangrong; Jin, Yi; Cheon, Seunghoon; Chun, Chang Ju; Wang, Zengtao; Archives of Pharmacal Research; vol. 40; 4; (2017); p. 435 – 443;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 876-31-3, name is 4-(Cyanomethyl)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. COA of Formula: C9H6N2

a) 4-Cyanophenylacetic acid 1 g (7.03 mMol) of 4-cyanophenylacetonitrile was added to conc. hydrochloric acid preheated to 105C and kept at this temperature for 5 minutes. It was cooled to 0C, the precipitate formed was collected and washed thoroughly with ice water. After purification by column chromatography on silica gel (Macherey-Nagel, 35-70 mesh ASTM) using ethyl acetate/methanol/glacial acetic acid = 95/5/0.5 (v/v/v) as eluant, 0.5 g (44% of theory) of colourless crystals were obtained Mp. 152.154C. IR (KBr): 2229.6 (C N), 1697.2 (Carboxylic acid-C=O) cm-1

The synthetic route of 4-(Cyanomethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; EP885186; (2003); B1;,
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. 6629-04-5, name is N-Cyanoacetylurethane, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O3

Example 19A 2-(1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid A solution of 3.65 g (23.4 mmol) of ethyl (cyanoacetyl)carbamate in 10 ml of ethanol was added to a solution of 8.5 g (103 mmol) of sodium acetate in 25 ml of water, and the mixture was stirred at RT for 2 h. In another flask, 5.00 g (23 4 mmol) of the compound from Example 18A were suspended in 10 ml of ethanol. 15 ml of water and 3 ml of conc. hydrochloric acid were added in succession. The mixture was cooled to 0 C., and a solution of 1.62 g (23.4 mmol) of sodium nitrite in 5 ml of water was slowly added such that the temperature did not exceed 2 C. At the end of the addition, this solution was stirred at 0 C. for another 30 min and then stirred into the ethyl (cyanoacetyl)carbamate solution which had been prepared beforehand. The reaction mixture was stirred at RT overnight. The suspension formed was diluted with 80 ml of 6N aqueous hydrochloric acid and stirred for 10 min The solid was filtered off with suction, washed with a little water, stirred with 200 ml of 2-propanol and filtered off again. The solid was suspended in 100 ml of glacial acetic acid, and 2.9 g (35.1 mmol) of sodium acetate were added. The mixture was heated at reflux temperature overnight. LC-MS of a small sample showed the intermediate 2-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile (Method 1, Rt=0.62 min; m/z=299 (M+H)+.). The mixture was cooled slightly (to about 95 C.), 19 ml of conc. hydrochloric acid were added and the mixture was heated at reflux for 3 days, with the reaction being monitored by LC-MS. After complete hydrolysis, the mixture was allowed to cool to RT and then added to 1.5 l of ice-water. The solid formed was filtered off, washed with diethyl ether and dried under HV. This gave 4.10 g (54% of theory) of the title compound. LC-MS (Method 6): Rt=0.51 min; m/z=318 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta[ppm]=3.37 (s, 3H), 7.16-7.27 (m, 2H), 7.30 (d, 1H), 12.54 (br. s, 1H), 13.67 (br. s, 1H). (signal of one methyl group probably hidden under the water signal).

The synthetic route of 6629-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; FUeRSTNER, Chantal; ACKERSTAFF, Jens; STRAUB, Alexander; MEIER, Heinrich; TINEL, Hanna; ZIMMERMANN, Katja; ZUBOV, Dmitry; SCHAMBERGER, Jens; (35 pag.)US2016/287599; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4387-31-9, 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. 4387-31-9, name is 4-Chloro-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of NaH (1.95 eq) in DMF (20 ml) are added 5.2 g of 1-butyl-piperidin-4-ol (Preparation 3, step A), the mixture is heated 3 h at 60 C., then 4-chloro-3-methyl-benzonitrile (1 eq) in DMF (20 ml) is added and heating continued for a further 4 h at 90 C. After evaporation to dryness, the residue is redissolved in water, extracted with TBME, the organic layer is washed with a 1 N aqueous solution of NaOH then with an aqueous NaCl solution, dried over MgSO4, filtered and evaporated. 4.5 g of the desired product are isolated after chromatography on silica eluting with a DCM/MeOH/NH4OH mixture (95:5:0.5 v/v/v).

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-Chloro-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEREP; US2009/233910; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts