Category: nitriles-buliding-blocks

Related Products of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, 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) 3-Bromo-6-fluoro-2-methylbenzonitrile To a cooled (0 C.) solution of 2-fluoro-6-methylbenzonitrile (2 g, 14.8 mmol) in concentrated sulfuric acid (40 mL) was added NBS (2.7 g, 15.6 mmol). The resulting residue was stirred at 0 C. for 3 hrs and poured into ice-water (400 mL). The resulting solution was extracted three times with EtOAc (80 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography to yield 3-bromo-6-fluoro-2-methylbenzonitrile.

The synthetic route of 198633-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Sui, Zhihua; Subasinghe, Nalin; US2014/275172; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 15666-97-4, 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. 15666-97-4 name is Octyl 2-cyanoacetate, 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.

Preparation of aryl-bis-(2-cyano-3-hydroxy-acrylic acid) ester (102): R = N-OCTYL, I-OCTYL (102) A 1.6 m solution MMOL of n-BuLi in hexane is added at-10C to a solution of 1 mmol diiso- propylamine in THFabs (6 ML/ML DIISOPROPYLAMINE). The mixture is stirred for 15 min. and than cooled down to-78C. After that the solution of 0.5 mmol of the corresponding cyano acetate is added in THF (1 MI/ g cyanoacetate) at this temperature initially, additionally stirred for 15 min and than the SOLU- tion of 0.5 mmol of the acid chloride is added in THF (2 ML/G acid chloride). After stirring of 45 min AT-78C the reaction mixture is quenched at this temperature with 15 % HCI und warmed up to room temperature over night.

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

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2005/12235; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

16532-79-9, name is 4-Bromophenylacetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 4-Bromophenylacetonitrile

To a solution of (4-bromo-phenyl)-acetonitrile (1 g, 5.10 mmol) in DMF (10 mL) is added sodium hydride (0.408 g, 10.20 mmol, 60% in mineral oil) at 0 C. The reaction mixture is stirred at 0 C. for 15 minutes and then methyl iodide (0.69 mL, 11.22 mmol) is added at 0 C. The reaction mixture is stirred at room temperature for overnight. The reaction mixture is quenched with aqueous ammonium chloride solution (5 mL) and extracted with EtOAc (2*20 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated. The crude material is purified over silica gel column chromatography (combiflash) eluting with 5-10% EtOAc in hexanes to give an off white solid (0.9 g, 78%). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J=8.4 Hz, 1H), 7.34 (d, J=8.4 Hz, 1H), 1.77 (s, 3H).

The synthetic route of 16532-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; Hamdouchi, Chafiq; Maiti, Pranab; Miller, Anne Reifel; (41 pag.)US2016/333005; (2016); 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(4-Aminophenyl)-2-methylpropanenitrile

1. Preparation of methyl 6-chloro-4-(4-(2-(cyanopropan-2-yl)phenylamino) -1,5-naphthyridine-3-carboxylate Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (5.0g, 18.4mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (2.96g, 18.5mmol) were dissolved in 1,4-dioxane (80mL). The reaction was conducted with stirring under reflux for 4hrs. The reaction mixture was cooled, and concentrated in a reduced pressure. The resulting solid was dissolved with dichlormethane, successively washed with saturated aqueous sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated in a reduced pressure to produce 6.54g of the title compound as a pale-yellow solid in a yield of 90.2%.

The synthetic route of 115279-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; ZHANG, Yan; EP2719697; (2014); 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. 1187-42-4, name is Diaminomaleonitrile, A new synthetic method of this compound is introduced below., Quality Control of Diaminomaleonitrile

Example 1-1; Methanol, in an amount of 216 mL, was placed in a four-necked flask with a volume of 500 mL, and 108.1 g (purity: 98.7percent, 0.987 mol) of DAMN and 116.73 g (1.100 mol) of trimethyl orthoformate were added thereto. p-Toluenesulfonic acid, monohydrate, in an amount of 190 mg, was added to the aforementioned mixture, and the reaction mixture was stirred while maintaining the temperature at 65¡ãC. 45 minutes after stirring was started, crystals of MMD were precipitated, and completion of the reaction was suggested. After the reaction mixture was stirred for 1.5 hours, the reaction mixture was cooled to 5¡ãC. The crystals were filtered and washed with 100 mL of cooled methanol, followed by drying. Thereby, 118.56 g (0.852 mol, yield = 80percent) of methyl N-(2-amino-1,2-dicyanovinyl)formimidate (MMD) was obtained.

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; Nippon Soda Co., Ltd.; EP2138480; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 42872-74-2,Some common heterocyclic compound, 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, molecular formula is C8H6BrN, 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.

[0332] 2-Fluoro-5-iodobenzonitrile (0.41 mg, 1.7 mmol), triphenylphosphine (0.088 g, 0.33 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.076 mg, 0.084 mmol) were dissolved in THF (15 ml) and flushed with nitrogen. Themixture was treated with 1-(4-ethynyl-4-hydroxypiperidin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone (520 mg, 1.7mmol) followed by tetrabutylammonium fluoride solution in THF (1.0 M, 3.3 ml, 3.3 mmol), sealed and placed in an oilbath at 60 C for 3 h. The mixture was cooled, diluted with water and ethyl acetate, and the layers separated. After theaqueous was extracted with additional ethyl acetate (2x), the combined organics were washed successively with water(2x) and brine, dried (Na2SO4) and concentrated. The resulting residue was purified by MPLC (eluent gradient 10->50%EtOAc:hex.) to provide 2-fluoro-5-[(4-hydroxy-1-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperidin-4-yl)ethynyl]benzonitrile:_[0361] 3-[(4-Hydroxy-1-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperidin-4-yl)ethynyl]-4-methylbenzonitrile was preparedin a similar fashion to that described for the synthesis of EXAMPLE 10 starting from 1-(4-ethynyl-4-hydroxypiperidin-1-yl)-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone and 3-bromo-4-methylbenzonitrile. 1H NMR (500 MHz, CDCl3, delta in ppm): 9.02(s, 1H), 7.72 (d, J = 8.5 Hz, 2H), 7.61 (s, 1H), 7.52 (d, J = 8.5 Hz, 2H), 7.36 (m, 2H), 4.06 (m, 1H), 3.89 (s, 2H), 3.76 (m,1H), 3.59 (m, 1H), 3.35 (m, 1H), 2.51 (s, 3H), 2.08 (m, 2H), 1.91 (m, 2H).

The synthetic route of 42872-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
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 1813-33-8 as follows. Recommanded Product: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 633336-81-9, These common heterocyclic compound, 633336-81-9, name is 4-(Aminomethyl)-3,5-difluorobenzonitrile, 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 4-aminomethyl-2,6-difluorobenzonitrile (0. [876] g, 5.21 mmol; see step (vi) above) was dissolved in 50 mL of THF and di-tert-butyl dicarbonate (1.14 g, 5.22 mmol) in 10 mL of THF was added. The mixture was stirred for 3.5 h. The THF was evaporated and the residue was partitioned between water and EtOAc. The organic layer was washed three times with 0.5 M HCI and water, dried (Na2SO4) and evaporated. The product could be used without further purification. Yield: 1. 38 g (99%). [‘H] NMR (300 MHz, [CDC13)] 8 7.21 (m, 2H), 4.95 (broad, 1H), 4.43 (broad, 2H), 1.52 (s, 9H)

The synthetic route of 633336-81-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2003/101957; (2003); 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. 1223434-15-8, name is Methyl 4-bromo-2-cyanobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 4-bromo-2-cyanobenzoate

A mixture of Compound II (980 mg), 2N aqueous lithium hydroxide solution (6.1 mL) and methanol (18 mL) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with 4N hydrochloric acid, and then extracted with chloroform. The chloroform layer was dried over sodium sulfate, and then concentrated under reduced pressure to give Compound III (808 mg).

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; Dainippon Sumitomo Pharma Co., Ltd.; HORIUCHI, Yoshihiro; FUJIWARA, Hiroaki; SUDA, Hitoshi; SASAKI, Izumi; IWATA, Mitsutaka; SAWAMURA, Kiyoto; EP2612848; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4107-65-7, 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. 4107-65-7, name is 2,4-Dimethoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 8-(2,4-Dimethoxy-phenyl)-purine A mixture of 2 g of 4,5-diamino-pyrimidine, 4 g of 2,4-dimethoxy-benzonitrile, 6 g of p-toluene sulfonic acid hydrate, and 40 ml of benzene was heated, whereby the benzene was distilled off. The residue was heated for 30 minutes at 120 C. After cooling the residue was triturated with 2 N ammonia and extracted with ethyl acetate. The ethyl acetate phase was extracted with 2 N hydrochloric acid, the aqueous phase was neutralized and again extracted with ethyl acetate, and subsequently the organic phase was extracted with 2 N sodium hydroxide solution. When the aqueous phase was neutralized, the product was precipitated and recrystallized from water. Yield: 0.15 g (3% of theory), M.P.: 221 C. (decomp).

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

Reference:
Patent; Boehringer Ingelheim Gesellschaft mit beschrankter Haftung; US4299834; (1981); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts