Category: nitriles-buliding-blocks

Application of 57381-51-8,Some common heterocyclic compound, 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, molecular formula is C7H3ClFN, 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 13: 1-(4-chloro-2-(piperidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea Preparation of 4-chloro-2-(piperidin-1-yl)benzonitrile 16ah (scheme 8) To commercially available 2-fluoro-4-chlorobenzonitrile (2.2 g, 12.87 mmol) piperidine (4equiv., 5.6 ml) was added and the solution was heated at 80C overnight. The reaction was evaporated and to the residue water was added and the solid material was filtrated, washed with water and dried obtaining 3 g of a pale yellow solid. Yield = 97% 1HNMR (DMSO, 200 MHz) delta 1.54 (2H, m), 1.65 (4H, m), 3.14 (4H, m), 7.09 (1H, dd, J = 8.2 Hz, J’ = 2 Hz), 7.14 (1H, m), 7.69 (1H, d, J = 8.4 Hz)

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
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Related Products of 13544-06-4,Some common heterocyclic compound, 13544-06-4, name is 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, molecular formula is C9H5F3N2O2, 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.

1.75 g (7.6 mmol) (2-Nitro-4-trifluoromethylphenyl)-acetonitrile in 20 ml THF are cooled to 0C in a nitrogen atmosphere and treated with 60 mi BH3/THF- complex (1 M in THF). The reaction mixture is allowed to slowly warm up to room temperature overnight. After 72 h the reaction solution is slowly given to 50 ml 5 N HO gegeben and then 1 h heated to reflux. The reaction mixture is evaporated to dryness, the residue made alkaline (pH 12-14) with 25% NaOH solution and extracted 2x with 100 mi ethylacetate. The combined organic phases are washed with brine, dried using Na2SO4, filtered and evaporated. Yield : 1.8 g (77 %) 112, brown oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; WO2005/75425; (2005); A2;,
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Synthetic Route of 31643-49-9, A common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

9.2 g of 4-nitrophthalonitrile, 5.0 g of phenol, 7.3 g of potassium carbonate and 40 ml of DMSO were added under the protection of an inert gas such as nitrogen, and the mixture was stirred at room temperature for 48 hours,The mixture was then heated to 60 C for 2 hours and then heated. After cooling, the mixture was precipitated and filtered to give a yellow solid which was dried to give 11.6 g of compound 1.

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; BEIJING BETA PHARMA, INC.; (43 pag.)TWI582078; (2017); B;,
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Synthetic Route of 193290-27-6, These common heterocyclic compound, 193290-27-6, name is 3-(2-Hydroxyethyl)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.

General procedure: To a cooled (0 C) solution of S154 (150 mg, 1.019 mmol) in CH2Cl2 (8 mL) were added MsCl (0.16 mL, 2.038 mmol) and Et3N (0.43 mL, 3.057 mmol). After stirring for 0.5 h at 0 C, brine was added. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. To a cooled (0 C) solution of the crude mixture in THF/DMF (4/1, 15 mL) were added TrtSH (1.13 g, 4.076 mmol) and NaH (60% dispersion in mineral oil, 163 mg, 4.076 mmol). After stirring for 16 h at 25 C, the reaction mixture was quenched by the addition of saturated NH4Cl solution and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexanes = 1/30) to afford S16 (1.8 g, 94% for two steps)

Statistics shows that 3-(2-Hydroxyethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 193290-27-6.

Reference:
Article; Kim, Bumki; Park, Heekwang; Salvador, Lilibeth A.; Serrano, Patrick E.; Kwan, Jason C.; Zeller, Sabrina L.; Chen, Qi-Yin; Ryu, Soyoung; Liu, Yanxia; Byeon, Seongrim; Luesch, Hendrik; Hong, Jiyong; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3728 – 3731;,
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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 110301-23-0 as follows. HPLC of Formula: C7H4F2N2

Step 9 While stirring 420 cm3 of concentrated sulfuric acid on an ice water bath, 54 g (0.78 mol) of finely pulverized NaNO2 was added at a rate which maintained the temperature below 40 C. The mixture was stirred on a warm water bath at 50 C. until the crystals were completely dissolved. The solution was stirred on an ice water bath and 700 cm3 of glacial acetic acid was added drop-wise. 108 g (0.70 mol) of 4-amino-3,5-difluorobenzonitrile was added at a rate which maintained the temperature at 20-25 C. and the mixture was stirred at that temperature until the crystals were completely dissolved to form the corresponding diazonium salt. An aqueous solution of the diazonium salt was added drop-wise for 2 hours to a solution of 143 g (1.0 mol) of copper (I) bromide dissolved in 420 cm3 of 47% hydrobromic acid while stirring on an ice water bath. The resulting solution was stirred for one hour on an ice water bath and allowed to sit overnight at room temperature. The product was filtered, washed with glacial acetic acid and recrystallized from a solvent mixture of acetone and methanol to yield 98 g (0.45 mol) of 4-bromo-3,5-difluorobenzonitrile.

According to the analysis of related databases, 110301-23-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Seiko Epson Corporation; US5200110; (1993); A;,
Nitrile – Wikipedia,
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Related Products of 330792-69-3, These common heterocyclic compound, 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, 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.

1,1-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 hour. 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.

Statistics shows that 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile is playing an increasingly important role. we look forward to future research findings about 330792-69-3.

Reference:
Patent; Pharmacyclics, Inc.; US7718662; (2010); B1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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 6330-25-2, Recommanded Product: 6330-25-2

General procedure: Sodium metal (46 mg, 2.0 mmol) was placed in a flask, equipped with reflux condenser and calcium chloride tube,and dissolved in absolute ethanol (4-5 ml). The obtained solution was treated with a mixture of the appropriate 3-carbamoylchromone 3 (1 mmol) and cyanoacetamide(2 mmol) and refluxed with stirring for 2 h. After coolingthe reaction mixture to room temperature, regardless of the presence of precipitate, the mixture was stirred and neutralized with 1 N HCl. The obtained fine crystalline precipitate was filtered off, washed with ethanol, dried, and recrystallized from a 1:3 mixture of DMF-EtOH.

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-Cyano-N-methyl-acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kornev, Mikhail Yu.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Ya.; Chemistry of Heterocyclic Compounds; vol. 51; 7; (2015); p. 688 – 690; Khim. Geterotsikl. Soedin.; vol. 51; 7; (2015); p. 688 – 690,3;,
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Adding a certain compound to certain chemical reactions, such as: 31643-49-9, name is 4-Nitrophthalonitrile, 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 31643-49-9, category: nitriles-buliding-blocks

Mixture of 4-Hydroxybenzaldehyde 1 (0.122g, 1 mmol), 4-Nitrophthalonitrile 2 (0.173 g, 1 mmol) and K2CO3 (0.138 g, 1 mmol) were dissolved in 2 mL DMF. The mixture was stirred at room temperature for 24 h. After completion of the reaction, 1 mL acetone and 5 mL water was added respectively to the reaction mixture, the resulting precipitates were separated and washed with 10 ml hot water and 10 ml hot ethanol.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Karimi, Ali Reza; Khodadadi, Azam; Tetrahedron Letters; vol. 53; 39; (2012); p. 5223 – 5226;,
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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 628-20-6 as follows. category: nitriles-buliding-blocks

4-chloro-nitrile (103.5mg, 1.0mmol, 5.0equiv. ) And Na 2 S 2 O 3 ¡¤ 5H 2 O (248.2mg, 1.0mmol, 5.0equiv. After) was added to the reaction tube, followed by addition of the reaction solvent of ethanol / water (0.25mL / 0.5mL), and stirred at a reaction temperature of 100 C for 2 hours. Then the reaction system was cooled, the solvent was removed under reduced pressure, followed by addition of Sodium trifluoromethylbenzene (46.5mg, 0.2mmol, 1.0equiv.), Then added to the reaction solvent, 1,4-dioxane ring (1.0mL), and stirred at a reaction temperature of 110 C for 11 hours. The reaction solution was cooled to room temperature. Methylbenzoate was then added triphenylphosphine (36.5mg, 0.12mmol, 0.6equiv.), Stirred at room temperature for 4 hours, the reaction solution under reduced pressure and finally the solvent removed to give product 20 after column chromatography (elution agent polarity: stone ether / ethyl acetate 40:1). Yield: 62%

According to the analysis of related databases, 628-20-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; East China Normal University; JIANG, XUEFENG; XIAO, XIAO; FENG, MINGHAO; (30 pag.)CN104387303; (2016); B;,
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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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Method 10B: the bromophenol was prepared using the appropriate fluorobromobenzene with methanesulfonylethanol.Under inert atmosphere, to a solution of the fluorinated derivative in dimethylformamide was added methylsulfonylethanol (1.5eq). The mixture was stirred at 0 C. before adding sodium hydride (5eq). The reaction mixture was stirred at room temperature, then acidified with 1M hydrochloric acid solution to pH 2, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 10.4. 2-bromo-4-hydroxybenzonitrile Prepared following the method previously described (Method 10B) using 2-bromo-4-fluorobenzonitrile. The product was chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 90/10 to 80/20). The product was obtained as a white solid. Yield: 95% Rf (petroleum ether/ethyl acetate 70/30): 0.25 NMR 1H (CDCl3): 5.95 (s, 1H); 6.87 (dd, 1H, J=8.5 Hz, J=2.4 Hz); 7.17 (d, 1H, J=2.4 Hz); 7.54 (d, 1H, J=8.5 Hz).

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; GENFIT; US2010/4159; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts