Month: June 2021

Reference of 60758-87-4, The chemical industry reduces the impact on the environment during synthesis 60758-87-4, name is 3,4-Diethoxybenzonitrile, I believe this compound will play a more active role in future production and life.

Reference Example 3 A solution of 29 g of 3,4-diethoxybenzonitrile and 23 g of thioacetamide in 120 ml of 10% hydrochloric acid-DMF was sirred at 90 C. for 3 hours and then 130 C. for 5 hours. After evaporation of the solvent, the residue was washed with diethyl ether (2*100 ml) and water (2*100 ml). The resulting crystals were collected by filtration and dried to obtain 21.7 g of 3,4-diethoxythiobenzamide.

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, 3,4-Diethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US6291487; (2001); 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. 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Amino-4-chlorobenzonitrile

Cyclohexanone (36mL), 2-amino-4-chlorobenzonitrile (4.6g, 30mmol) and zinc chloride (4.1g, 30mmol) were mixed in a flask and the mixture was heated to 120C for 3h. Following cooling to room temperature and evaporation of the solvent, the residue was diluted with ethyl acetate (30mL) and the solid was collected by filtration. A 10% aqueous solution of NaOH (50mL) was added. After stirring for 2h, the mixture was filtered, and the filter cake was washed with water and extracted with methanol. The combined extracts were concentrated to afford the desired product (4.7g) in 67% yield. 1H NMR (400MHz, DMSO) delta 8.17 (d, J=9.0Hz, 1H), 7.62 (d, J=2.0Hz, 1H), 7.28 (s, 1H), 6.46 (s, 2H), 2.81 (d, J=5.5Hz, 2H), 2.52 (s, 2H), 1.80 (d, J=4.7Hz, 4H). LC/MS (ESI): m/z 233.2 [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:
Article; Sun, Yang; Chen, Jianwen; Chen, Xuemin; Huang, Ling; Li, Xingshu; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7406 – 7417;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 261762-98-5,Some common heterocyclic compound, 261762-98-5, name is 3-Chloro-2-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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.

Example S59; Preparation of 2-(3-chloro-2-fluoro-phenyl)-ethylamine hydrochloride; 1.87 g of (3-chloro-2-fluoro-phenyl)-acetonitrile (11 mmol) were dissolved in 18 ml THF and cooled down to 0 C. under nitrogen. 58 ml of a 1M borane-THF complex solution in THF (58 mmol) were then added dropwise over 20 min by keeping the temperature between 0 to 2 C. After addition the reaction mixture was stirred at rt for additional 20 min, and refluxed for 21 h. The reaction mixture was then cooled down to 0 C. and treated between 2 and 5 C. with 13 ml methanol over a period of 35 min. After 1 h refluxing the reaction mixture was concentrated, the residue dissolved in DCM and the amine extracted twice with 1N aqueous HCl. The combined aqueous phases were then treated with concentrated NaOH to adjust the pH to 12, and then extracted twice with DCM. The combined organic phases were then washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo leading to 1.6 g colorless oil. This was dissolved in 50 ml diethylether, treated with 5 ml 2.6N HCl in diethylether, stirred at rt for additional 60 min, filtered and dried under high vacuo, leading to 1.6 g white solid (69%). MS (ISP) 174.2 (M+H)+.

The synthetic route of 261762-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Conte-Mayweg, Aurelia; Kuehne, Holger; Luebbers, Thomas; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2006/30613; (2006); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 76469-88-0, 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. 76469-88-0 name is Methyl 4-(cyanomethyl)benzoate, 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.

A 100 mL flask was charged with methyl 4-(cyanomethyl)benzoate (1 g, 5.7 mmol), acetonitrile (46 mL), cesium carbonate (5.6 g, 17 mmol) and 1,2-dibromoethane (1.3 g, 5.8 mmol). The resulting suspension was stirred at 80C for three hours, cooled at room temperature and quenched with water (30 mL). The aqueous mixture was extracted with ethyl acetate (2 × 20 mL), the combined organic phases were washed with water (5 mL), brine (5 mL), dried with Na2SO4, filtered and evaporated. Purification by chromatography over silica gel (cyclohexane/ethyl acetate gradient, 1:01:1) affords methyl 4-(1-cyanocyclopropyl)benzoate. (0527) 1H-NMR (400 MHz, CDCl3): d = 8.05-8.00 (m, 2H), 7.37-7.33 (m, 2H), 3.93 (s, 3H), 1.85-1.80 (m, 2H), 1.51-1.47 (m, 2H); ); (0528) LC-MS (method 1): Rt 0.87, m/z = 202 (M+1).

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

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel, Henri; EDMUNDS, Andrew; EMERY, Daniel; HALL, Roger, Graham; HUETER, Ottmar, Franz; KOLLETH KRIEGER, Amandine; RENDLER, Sebastian; SCHAETZER, Juergen, Harry; (0 pag.)WO2020/2563; (2020); A1;,
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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. 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(2-Nitrophenyl)acetonitrile

Absolute ethanol (2,250 ml) and 1,500 g (9.25 moles) of o-nitrophenylacetonitrile is charged into a 22 liter flask. The suspension is cooled to 5-10 and hydrogen chloride is bubbled into the mixture for 2.5 hours. The reaction mixture is stirred at 10 under nitrogen atmosphere overnight. It is then diluted with 16,000 ml of ether and stirred for 1 hour; the solid is collected by filtration, washed with 4*1,000 ml of ether and dried (5 mm Hg/40) to give ethyl 2-(o-nitrophenyl)-acetimidate hydrochloride, m.p. 122-123 (dec).

The synthetic route of 610-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4595535; (1986); A;,
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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 5922-60-1 as follows. name: 2-Amino-5-chlorobenzonitrile

General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sadeghzadeh, Seyed Mohsen; Catalysis Communications; vol. 72; (2015); p. 91 – 96;,
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Application 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.

Example 5A 3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenecarbonitrile Under argon, 3.60 g (18.0 mmol) of 3-bromo-5-fluorobenzenecarbonitrile, 5.03 g (19.8 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane and 5.30 g (54.0 mmol) of potassium acetate are provided in 72 ml of degassed 1,4-dioxane/DMSO (10/1), and 441 mg (0.54 mmol) of 1,1′-bis(diphenylphosphine)ferrocenedichloropalladium(II)/dichloromethane complex are added. The mixture is stirred at 90 C. overnight. Water is subsequently added, the phases are separated, the aqueous phase is extracted with ethyl acetate and the combined organic phases are concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1). 4.48 g (92% of theory) of the title compound are obtained. 1H-NMR (400 MHz, DMSO-d6): delta=8.01 (ddd, 1H), 7.82 (s, 1H), 7.70 (ddd, 1H), 1.32 (s, 12H). GC-MS (Method 11): Rt=4.94 min; MS (EIpos): m/z=247 [M]+.

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; AiCuris GmbH & Co. KG; US2012/22123; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6, 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Amino-2-trifluoromethylbenzonitrile, (2.23 g, 12 mmol) was added portionwise over15 minutes into the well-stirred heterogeneous mixture of thiophosgene (1 ml, 13 mmol) in water (22 ml) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3 x 15 ml). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product, 4-isothiocyanato-2-trifluoromethylbenzonitrile, (Ia), as brownish solid and was used as such for the next step (2.72 g, 11.9 mmol, 99%).

The chemical industry reduces the impact on the environment during synthesis 4-Cyano-3-trifluoromethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/124118; (2006); 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 103146-25-4 as follows. Formula: C20H23FN2O2

In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4.

According to the analysis of related databases, 103146-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
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Synthetic Route of 222978-02-1, These common heterocyclic compound, 222978-02-1, name is 2-Fluoro-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 a solution of 2-fluoro-4-(hydroxymethyl)benzonitrile (400 mg, 2.65 mmol) and TEA (0.738 mL, 5.29 mmol) in DCM (10 mL) was added methanesulfonyl chloride ( 1.27 g, 11.1 mmol) at 0 C, and the reaction mixture was stirred for 16 h at 16 C. The reaction mixture was concentrated in vacuo to give 4-cyano-3-fluorobenzyl methanesulfonate as an oil. ESI-MS m/z [M + H]+: low ionization.

The synthetic route of 222978-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; WANG, Deping; FRALEY, Mark, E.; JONES, Kristen, G.; (273 pag.)WO2017/222951; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts