Month: September 2021

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;,
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Synthetic Route 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;,
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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. 49674-16-0, name is 5-Amino-3-bromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Amino-3-bromobenzonitrile

To a stirring solution of 103 mg (0.520 mmol) of 3-amino-5-bromobenzonitrile in 3 mL of pyridine was added 0.12 mL (1.27 mmol) Of Ac2O. The solution was stirred at r.t. for about 5.5 h and concentrated. Ethyl acetate was added, and the organic layer was washed with H2O and brine, dried over Na2SO4, filtered and concentrated. N-(3-bromo-5- cyanophenyl)acetamide was used for the next reaction without further purification.

According to the analysis of related databases, 49674-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
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Electric Literature of 874-97-5,Some common heterocyclic compound, 874-97-5, name is 3-Cyanobenzyl alcohol, molecular formula is C8H7NO, 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.

e 2-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester Diethyl azodicarboxylate (174 mg, 1.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxyphenyl ester (285 mg, 1.0 mmol), as prepared in the preceding step, 3-cyanobenzyl alcohol (133 mg, 1.0 mmol)(Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (263 mg, 1.0 mmol) in tetrahydrofuran (10 mL) at 0 C. The mixture was stirred at 0 C. for 2 hours and at room temperature for 3 hours. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3*30 mL). The organic phase was washed with saturated NaHCO3 (2*30 mL), brine (2*30 mL) and dried over Na2 SO4. The solvent was removed in vacuo the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a pale yellow oil (375 mg, 93%). 1 H-NMR (300 MHz, CDCl3) delta 5.02 (s, 2H), 6.78 (m, 2H), 6.85 (dd, 1H, J=4.2, 1.3 Hz), 7.20 (t, 1H, J=8.2 Hz), 7.38 (t, 1H, J=5.8 Hz), 7.51 (t, 1H, J=7.7 Hz), 7.59-7.68 (m, 5H) and 7.93 (dd, 1H, J=4.0, 0.7 Hz).

The synthetic route of 874-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US6034127; (2000); A;,
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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. Safety of 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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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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Application of 105-34-0,Some common heterocyclic compound, 105-34-0, name is Methyl 2-cyanoacetate, molecular formula is C4H5NO2, 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 10 mL round-bottomed flask was charged with carbonyl compound (1 mmol), active methylene compound (1 mmol), S-4 (12 mg and 20 mol% of the substrates), and water (3 mL). The reaction mixture was stirred at room temperature. The suspension was stirred at room temperature for the lengths of time shown in Table 4. The reaction progress was monitored by thin layer chromatography usingn-hexane-EtOAc (5:1) as eluent. After completing the reaction, the reaction mixture solidified in the round-bottomed flask. The solids were then dissolved in hot ethanol (30 mL). The catalyst was removed by filtration and washed with ethanol. The solid product was obtained after the ethanol was concentrated in vacuo.

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

Reference:
Article; Zhao, Xian-Liang; Yang, Ke-Fang; Zhang, Yan-Ping; Zhu, Ju; Xu, Li-Wen; Chinese Chemical Letters; vol. 25; 8; (2014); p. 1141 – 1144;,
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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. SDS of cas: 103146-25-4

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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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;,
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Related Products 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