Month: June 2021

Application of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 2: (Z)-N’ -hydroxybenzo[d][l,3]dioxole-5-carboximidamide To a solution of benzo[d][l,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2C03 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80C for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1L><4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N'-hydroxy benzo[d][l,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS(ES+) m/z 181.1 (MH+). The synthetic route of 3,4-(Methylenedioxy)benzonitrile has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; WANG, Rong; LU, Hongtao; WO2013/107336; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. Quality Control of 5-Fluoro-2-nitrobenzonitrile

[0593] (a) Preparation of 5-[((2S)-1-methylpyrrolidin-2-yl)methoxy]-2-nitrobenzenecarbonitrile. To a slurry of 60% NaH (956 mg, 24 mmol) in THF (100 mL) was added (S)-(-)-1-methyl-2-pyrolidinemethanol (Aldrich) (2.8 mL, 24 mmol) resulting in gas evolution. After 30 min, 5-fluoro-2-nitrobenzonitrile (Combi Blocks) (3.3 g, 20 mmol) was added. After 3 h the reaction solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4 and concentrated in vacuo to give a red oil. MS m/z: 262 (M+1). Calc’d for C13H15N3O3-261.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-78-0, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, 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 34662-24-3, Quality Control of 2-Chloro-3-nitrobenzonitrile

A solution of anhydrous EtOH (20 mL) was bubbled through NH3 at 0C to obtain 7M NH3/EtOH. It was transfered intoa sealed tube containing 2-chloro-3-nitrobenzonitrile (0.5 g, 2.7 mmol, 1.0 eq). The mixture was allowed to warm to 18C gradually and then stirred at 110C for 12 hours. The mixture was evaporated under reduced pressure to remove the most solvent to give 0.5 g of crude 2- amino-3-nitrobenzonitrile as a yellow solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 330792-69-3, 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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

l,l-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1 , 1 -dicyano-2-methoxy-2- (4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 h. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol: water (4:1) and then dried in air to give 3-amino-4- cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

The chemical industry reduces the impact on the environment during synthesis 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACYCLICS, INC.; CHEN, Wei; LOURY, David, J.; MODY, Tarak, D.; WANG, Longcheng; WO2013/10136; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 859855-53-1, name is 3-Amino-4-fluorobenzonitrile, molecular formula is C7H5FN2, 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. Application In Synthesis of 3-Amino-4-fluorobenzonitrile

Intermediate 28: (4-Fluoro-3-(pyrrolidin-l-yl)phenyl)methanamineStep 1: 4-Fluoro-3-(pyrrolidin-l-yl)benzonitrile3-Amino-4-fluorobenzonitrile (0.5 g, 3.67 mmol), 1 ,4-dibromobutane (0.439 ml, 3.67 mmol), sodium carbonate (0.779 g, 7.35 mmol) and toluene (3 ml) were added into a microwave vial. The resulting mixture was heated by microwave irradiation at 140 C for 2 hours. 1 ,4-dibromobutane (0.5 ml, 4.18 mmol) was added and the reaction mixture was irradiated at 140 C and at 160 C until the reaction had clearly stopped. The reaction mixture was diluted with dichloromethane and washed twice with water. The organic phase was dried over Na2S04, filtered and evaporated. The crude product was purified by column chromatography. 0.221 g of the title compound was obtained. NMR (400 MHz, CDC13) delta ppm 1.96 – 2.00 (m, 4 H) 3.39 – 3.48 (m, 4 H) 6.84 (dd, 1 H) 6.89 – 6.94 (m, 1 H) 6.96 – 7.04 (m, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 859855-53-1, its application will become more common.

Reference:
Patent; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; PIETIKAeINEN, Pekka; ROSLUND, Mattias; VAeISAeNEN, Emilia; WOHLFAHRT, Gerd; WO2012/152983; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 50670-64-9, name is 5-Amino-2-methylbenzonitrile, 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. Quality Control of 5-Amino-2-methylbenzonitrile

Add a solution of sodium nitrile (2.1 g, 31 mmol) in water (15 mL) drop wise at 5 C to a stirred solution of 5-amino-2-methylbenzonitrile (4.0 g, 31 mmol) in 33% sulfuric acid (45 mL) and keep the temperature below 5 C. In a separate flask, add concentrated sulfuric acid (30 mL) cautiously to a stirred solution of sodium sulfate (21.7 g, 153 mmol) in water (15 mL) and heat the mixture to reflux. Add the prepared diazonium solution to the re fluxing mixture in portions and continue refluxing for 2 hours. Cool the mixture slowly to room temperature and stir overnight. Extract the mixture with ethyl acetate (2 x 100 mL) and wash the combined organic extracts with water (2 x 150 mL) and 10% NaOH water solution (3 x 100 mL). Acidify the combined NaOH extracts with concentrated HC1 and then extract with ethyl acetate (2 x 200 mL). Dry the organic extracts over Na2S04 and concentrate under reduced pressure to give the title compound as a yellow solid (2.4 g, 60%): ES/MS (m/z) 134 (M+H), which is used directly without further purification.

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

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Kevin Kun-Chin; XIE, Yinong; WU, Liang; ZHOU, Guoqiang; WO2015/89800; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 15760-35-7,Some common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

into a 500-mL 3-necked round-bottomflask, was placed a solution of 3-methylidenecyclobutane-1-carbonitrile (1.5 g, 16.11 mmol,1.00 eq.) and RuC13.H20 (360 mg, 1.60 mmol, 0.10 eq.) in DCMIACN/H20 (60/60/90 mL). This was followed by the addition of sodium periodate (5.2 g, 24.31 mmol, 1.50 eq.), in portions at 10C in 15 mm. The resulting solution was stirred for 2 hours at 25 C. The solids were filtered out. The resulting solution was extracted with dichloromethane (3×100 mL) andthe organic layers combined. The resulting mixture was washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.1 g (72%) of 3- oxocyclobutane-1-carbonitrile as a yellow solid.

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

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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: C7H3BrClN

To a solutionof 2-bromo-5-chlorobenzonitrile (20 g, 93 mmol) in THF (200 mL) was added cyclopropylmagnesiumbromide (558 mL, 279 mmol) at 0 C. The resulting reaction – 151 -mixture was stirred at 0-5 C for 5 hours before MeOH (100 mL) was added and stirring continued at room temperature for 15 min. NaBH4 (7.1 g, 186 mmol) was added subsequently and the reaction mixture was stirred at room temperature overnight. Water was added and reaction mixture was exacted with AcOEt (300 mL x 3). The combined organic layers were concentrated in vacuo to give a crude product which was then purified by chromatography to give (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (8.2 g, yield 34%).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); 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. 51762-67-5, name is 3-Nitrophthalonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H3N3O2

The phthalonitrile compund ( 5) was synthesized by the reaction between 5-Methyl-1,3,4-thiadiazole-2-thiol (1) and 3-nitrophthalonitrile (3) in dry DMF in the presence of K2CO3 according to literature [25].

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; Demirba?, Uemit; Pi?kin, Mehmet; Bayrak, R?za; Durmu?, Mahmut; Kantekin; Journal of Molecular Structure; vol. 1197; (2019); p. 594 – 602;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 19179-31-8, 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. 19179-31-8 name is 3,5-Dimethoxybenzonitrile, 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.

Adding 0.02 equivalents of anhydrous copper sulfate and 4.0 equivalents of potassium t-butoxide to a 25 mL Schlenk reaction tube, drying in vacuum for 15 minutes, and sequentially adding 1,4-dioxane 1.5 mL and t-butanol 1 mL under argon atmosphere, 3,5-dimethoxybenzonitrile 5.0 equivalents,1 mmol of 1-(phenylthio)benzyl-2-iodobenzene was placed in the reaction tube after adding polytetrafluoroethylene stopper was placed into an oil bath of the reaction 100 C for 4 h. After the reaction is completed, the solvent is removed by filtration, and the solvent is separated by column chromatography. The eluent is petroleum ether/dichloromethane/ethyl acetate (v:v:v=20:10:1) to give a yellow liquid as 2-(3,5-dimethoxyphenyl)-3-(phenylthio)-1H-indole. The yield was 98%

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

Reference:
Patent; University of Science and Technology of China; Kang Yanbiao; Shan Xianghuan; (12 pag.)CN108863894; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts