Month: March 2021

Synthetic Route of 53312-81-5, These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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 solution of (R)-tert-butyl [1-(2-chloro-6-propylpyrimidin-4-yl)piperidin-3-yl](methyl)carbamate (50 mg, 0.14 mmol) prepared in Preparation 28 and 5-amino-2-fluorobenzonitrile (23 mg, 0.17 mmol) in n-butanol (1 ml) was refluxed under stirring overnight. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=1/1?dichloromethane/methanol=10/1) and then dissolved in methanol. Hydrogen chloride gas was added to the solution. The reaction mixture was stirred at room temperature for 5 hours and then filtered to give 23 mg of the product as a pale yellow solid.

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; Lee, Hyun-Joo; Kim, Dong-Hoon; Kim, Tae-Kyun; Yoon, Young-Ae; Sim, Jae-Young; Cha, Myung-Hun; Jung, Eun-Jung; Ahn, Kyoung-Kyu; Lee, Tai-Au; US2013/331377; (2013); A1;,
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Reference of 15996-76-6, A common heterocyclic compound, 15996-76-6, name is 4-(Aminomethyl)benzonitrile hydrochloride, molecular formula is C8H9ClN2, 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.

100 g (0.593 mol) of 4-cyanobenzylamine¡ÁHCl were dissolved in 1.2 l of dioxane and 600 ml of 2 N NaOH. 142.3 g (0.652 mol) of di(tert-butyl)pyrocarbonates were added in two portions over 10 min at 0 C. The pH was adjusted to 9-10 by adding 2 N NaOH, and the mixture was stirred for a further 4 h. The solvent was removed in vacuo, and the residue was taken up with ethyl acetate, washed 3¡Á each with 5% KHSO4 and NaCl-saturated water and then dried over Na2SO4. The solvent was removed in vacuo (white solid). Yield: 132.6 g (0.57 mol) of white solid, HPLC: 51.6% B

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; Stuerzebecher, Joerg; Steinmetzer, Torsten; Schweinitz, Andrea; Sturzebecher, Anne; Donnecke, Daniel; US2007/66539; (2007); A1;,
Nitrile – Wikipedia,
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Application of 939-79-7, These common heterocyclic compound, 939-79-7, name is 4-Methyl-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.

A mixture of 4-methyl-3-nitrobenzontitrile (2.4Ig), 10% Pd on C ( ~lg) and ethanol was stirred under hydrogen. After 24 hours the reaction mixture was filtered through Celite, and the solvent reduced in vacuo and purified using flash chromatography to yield 3-amino-4-methyl-benzonitrile (1.2Ig).

Statistics shows that 4-Methyl-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 939-79-7.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/93049; (2009); A1;,
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Electric Literature of 58633-04-8, 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. 58633-04-8 name is 4-Amino-3,5-dibromobenzonitrile, 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.

EXAMPLE 26 PREPARATION OF 3,5-DIBROMOBENZONITRILE STR38 To a stirred solution of t-butylnitrite (53.5 muL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50 C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50 C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (9:1) as the eluant provided 28 mg (59%) of white, crystalline product. NMR (CDCl3) delta:7.7 (d, J=1.8Hz, 2H), 7.9 (t, J=1.8Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3,5-dibromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co. Inc.; US5455239; (1995); A;,
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Synthetic Route of 623-00-7,Some common heterocyclic compound, 623-00-7, name is 4-Bromobenzonitrile, molecular formula is C7H4BrN, 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: Preparation of biphenyl-4-carbonitrile (38): Pd(OAc)2 (2.3 mg, 1 mmol %), 4-bromo-benzonitrile (37) (182 mg, 1.0 mmol), 4,4,6-trimethyl-2-phenyl-[1,3,2] dioxaborinane (26) (224.4 mg, 1.1 mmol), Cs2CO3 (650 mg, 2 mmol), toluene (4 mL)-methanol (1 mL) were mixed together in a small reaction tube and the mixture was heated at 60 C. The reaction progress was followed by TLC (15% ethyl acetate:hexanes). After the starting materials were consumed the mixture was cooled and filtered through celite followed by washing with toluene. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (15% ethyl acetate:hexanes) to obtain the title compound in 95% yield. 1H NMR (400 MHz, CDCl3): delta 7.74-7.67 (m, 4H), 7.62-7.58 (m, 2H), 7.53-7.41 (m, 3H). 13C NMR (100.6 MHz, CDCl3): delta 145.9, 139.4, 133.7, 132.9, 132.8, 129.4, 128.9, 128.0, 127.5, 119.2, 111.1

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

Reference:
Article; Myslinska, Malgorzata; Heise, Glenn L.; Walsh, Dana J.; Tetrahedron Letters; vol. 53; 24; (2012); p. 2937 – 2941;,
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Electric Literature of 53312-79-1, 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. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Under nitrogen protection, a water separator was installed in a 2L four-necked flask, and 152.6 g of 2-chloro-5-cyanoaniline, 130 g of benzaldehyde, 12 g of p-toluenesulfonic acid and 1.2 L of xylene were added, and the mixture was refluxed for 6 hours.The reaction can be stopped without significant water droplets in the water separator.After cooling to room temperature, it was washed with 100 mL of 10% aqueous sodium hydroxide solution, and the organic phase was decomposed under reduced pressure.The obtained residue was distilled under reduced pressure to give 215 g of the desired product N-benzylidene-2-chloro-5-cyanoaniline. The gas chromatographic content was 98.4%, and the yield was 89.3%.

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

Reference:
Patent; Shanghai Kangpeng Technology Co., Ltd.; Zeng Yuan; Zhou Yan; Li Bolan; Chen Xiaobin; Wang Daoxiang; Yang Jianhua; (19 pag.)CN108276294; (2018); A;,
Nitrile – Wikipedia,
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Synthetic Route of 1194-02-1, The chemical industry reduces the impact on the environment during synthesis 1194-02-1, name is 4-Fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of BB8: 4-Fluoro-N-hydroxy-benzamidine; To a solution of the 4-fluoro-benzonitrile (10.0 g, 52.9 mmol) in ethanol (200 mL), the solution of NH2OH-HCl (4.0 g, 58.2 mmmol) in H20 (4 mL) was added dropwise. The mixture was stirred vigorously at about 65 C and stood overnight. The analysis by TLC indicated the complete consumption of starting material. The solution was concentrated to remove the solvent. The residue was dissolved in DCM and washed with water, brine, dried over Na2S04 and concentrated in vacuum to afford 4-Fluoro-N-hydroxy-benzamidine as pale- yellow solid (BB8).

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-Fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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Related Products of 21524-39-0, 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. 21524-39-0, name is 2,3-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 3-Fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile and 3-fluoro-2-(1 H-1 ,2,3-triazol-1 -yl)benzonitrile. A mixture of 2,3-difluorobenzonitrile (4.0 g, 28.8 mmol), 2H-1 ,2,3-triazole (1 .9 g, 28.8 mmol) in DMF (85.0 mL) and K2CO3 (7.9 g, 57.5 mmol) were heated to 125 C for 1 .5 h. After cooling to rt, water was added and the mixture extracted with EtOAc (2 X). The combined organics were washed with brine and dried (Na2SO ). Purification via FCC (10-100% EtOAc in hexanes) gave two products. 3-Fluoro-2-(2H-1 ,2,3-triazol-2- yl)benzonitrile (1 .6 g, 29%), 1H NMR (CDCI3): 7.99 (s, J = 6.6 Hz, 2H), 7.67 – 7.63 (m, 1 H), 7.61 – 7.53 (m, 2H), 7.26 (s, 6 H) and 3-fluoro-2-(1 H-1 ,2,3-triazol- 1 -yl)benzonitrile (2.0 g, 38%) 1H NMR (CDCI3): 7.97 (dd, J = 4.4, 2.8 Hz, 1 H), 7.95 (d, J = 1 .2 Hz, 1 H), 7.70 (tt, J = 5.7, 2.8 Hz, 1 H), 7.65 (td, J = 8.1 , 4.9 Hz, 1 H), 7.62 – 7.57 (m, 1 H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
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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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Formula: C9H6F3N

To a solution of 4- trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni ((at)4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95%). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+H).

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/110409; (2005); A2;,
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Electric Literature of 3288-99-1, The chemical industry reduces the impact on the environment during synthesis 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)acetonitrile, I believe this compound will play a more active role in future production and life.

In a 300 mL-reaction flask equipped with a rectification column and a separating tank, 11.3 g (65.2 mmol) of 4-tert-butylphenylacetonitrile, 10.8 g (59.5 mmol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 100 g of heptane, 10.0 g of 5-ethyl-2-picoline, and 3.0 g of diethylene glycol monoethyl ether were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 13.8 g (71.5 mmol) of 28% sodium methoxide methanol solution was added dropwise over 5 hours, and the resulting mixture was further reacted for 5 hours. After cooling to 30 C. or less, 108 g of water was added to separate out heptane phase and obtain an aqueous phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 17.0 g (yield 92.1%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

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, 2-(4-(tert-Butyl)phenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts