Category: nitriles-buliding-blocks

10412-93-8, These common heterocyclic compound, 10412-93-8, name is N-Benzyl-2-cyanoacetamide, 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: A mixture of N-alkyl-2-cyano-acetamides 1a-c (2 mmol), aldehydes 2a-f (2 mmol),malononitrile (3) (2 mmol), K2CO3 (2 mmol), and EtOH (2 mL) in a 10 mL septum-capped microwavevials was irradiated under microwave conditions at 90 C, 500 W, 200 rpm, for 10-15 min. Aftercompletion of the reaction, as indicated by TLC, each vial was de-capped and the contents were left tocool to room temperature. Then, the reaction mixture was worked up as described in method I to givecompounds 4a-q. Analytical samples were obtained by recrystallization from MeOH.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10412-93-8.

Reference:
Article; Mekheimer, Ramadan Ahmed; Al-Sheikh, Mariam Abdullah; Medrasi, Hanadi Yousef; Alsofyani, Najla Hosain Hassan; Molecules; vol. 23; 3; (2018);,
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13338-63-1, These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13338-63-1.

Reference:
Article; Madadi, Nikhil R.; Penthala, Narsimha R.; Howk, Kevin; Ketkar, Amit; Eoff, Robert L.; Borrelli, Michael J.; Crooks, Peter A.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 123 – 132;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-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. 77326-36-4

A solution of 2-amino-6-fluorobenzonitrile (10.0 g) in H2S04 (75.0 mL) was stirred for 1.5 h at 65 C. Then the mixture was poured into ice and brought to pH = 9 by 20% NaOH aqueous solution, followed by the extraction with ethyl acetate three times. The combined organic layer were washed with brine and dried over Na2S04. It was filtered to remove insoluble matters and it was concentrated in vacuo to give compound 1-1 as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 77326-36-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; HIRABAYASHI, Tomokazu; KATSUNO, Mika; SMITH, Cameron James; SHERER, Edward; CAMPEAU, Louis-Charles; BALKOVEC, James; GREENLEE, William John; LI, Derun; GUO, Liangqin; CHAN, Tin Yan; CHEN, Yi-Heng; CHEN, Yili; CHACKALAMANNIL, Samuel; TAN, John Qiang; WO2014/99694; (2014); A1;,
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118431-88-2, 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 118431-88-2 as follows.

[Example 4]; Production of 2-cyano-3-cyclopropyl-1-[1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridin-3-yl]propane-1,3-dione (Inventive Compound No. V-9); 1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (1.0g, 4.5 mmol) was dissolved in thionyl chloride (5 mL), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carbonyl chloride. The obtained acid chloride was dissolved in acetonitrile (20 mL), and added dropwise to a mixed solution of 3-cyclopropyl-3-oxopropanenitrile (0.49g, 4.5 mmol), triethylamine (0.55g, 5.4 mmol) and acetonitrile (10 mL), under ice cooling. After the stirring for a day at room temperature, acetonecyanhydrin (0.04g, 0.47 mmol) and triethylamine (0.55g, 5.4 mmol) were further added thereto, and the mixture was stirred for a day at room temperature. The reaction mixture was concentrated under reduced pressure, and thus obtained residue was added with a mixture of aqueous saturated sodium bicarbonate and ethyl acetate for liquid separation. The obtained aqueous layer was added with diluted hydrochloric acid to give a pH of 3 to 4, and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and thus obtained crystal was washed with ether, to obtain 0.29g of a subject compound (yield: 20%). 1H-NMR Data (CDCl3/TMS delta (ppm)): 1.24-1.31 (2H, m), 1.39-1.44 (2H, m), 2.35-2.43 (1H, m), 3.71 (3H, d), 6.77 (1H, d, J=7.4 Hz), 7.72 (1H, d, J=7.4 Hz), 17.2 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 118431-88-2, and friends who are interested can also refer to it.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY CO., LTD.; EP1982978; (2008); A1;,
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These common heterocyclic compound, 38487-86-4, name is 2-Amino-4-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. 38487-86-4

General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 38487-86-4.

Reference:
Article; Sun, Yajun; Jin, Weiwei; Liu, Chenjiang; Molecules; vol. 24; 21; (2019);,
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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. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 33143-29-2

General procedure: For NaIO4/imidazole system, the reaction was carried out with alkene (1 mmol), n-nonane (internal standard, 1 mmol), NaIO4 (2 mmol) and the catalyst (5% mmol) at 25 C for 5 h in the 2:1 mixture of acetonitrile : water. The catalyst was precipitated from the reaction mixture by adding hexane (10 mL), and then the organic phase was separated and purified on a silica gel column, and then analyzed by GC. The progress of the reaction was monitored by GC to find the optimal conversion and selectivity.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Jing; Liu, Sirui; Ma, Yan; Cai, Jiali; Journal of Organometallic Chemistry; vol. 886; (2019); p. 27 – 33;,
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The chemical industry reduces the impact on the environment during synthesis 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, I believe this compound will play a more active role in future production and life. 59997-51-2

Step j03: At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-ll) (1 eq., 5 g) was taken up in EtOH (100 ml), mixed with hydrazine hydrate (2 eq., 4.42 g) and refluxed for 3 h. The residue obtained after removal of the EtOH by distillation was taken up in water (100 ml) and extracted with EE (300 ml). The combined organic phases were dried over sodium sulphate, the solvent was removed under vacuum and the product (J-lll) (5 g, 89 % yield) was obtained as a light red solid after recrystallisation from hexane (200 ml).

The chemical industry reduces the impact on the environment during synthesis 59997-51-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; FRORMANN, Sven; WO2012/62463; (2012); A1;,
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1953-99-7, 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. 1953-99-7 name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

Synthesis Example 4: Synthesis of 3,4,6-trichloro-5-(2,6-difluoro-phenoxy)-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 2.45 g of 2,6-difluorophenol, 3.9 g of K2CO3, and 25 ml of N,N-dimethyl formamide were put in s 100 ml flask, and then stirred while heated at 70¡ã C. When the reaction was complete, EA (ethyl acetate) was used for an extraction. After the extraction, the resultant was concentrated to obtain a solid. Herein, the obtained solid was dissolved in a small amount of dichloromethane, and then several times washed with hexane, filtered, and vacuum-dried to obtain 3,4,6-trichloro-5-(2,6-difluoro-phenoxy)-phthalonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., 658-99-1

Example A1 Diastereomeric methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3,4-difluorophenyl)butanoate (Table 1, Examples 1-11) Under protective gas (Ar), 0.773 g (5.046 mmol) of (3,4-difluorophenyl)acetonitrile and 0.1 ml of sodium methoxide solution (30% in methanol) were added to 1.000 g (5.046 mmol) of methyl 3-(2,6-difluorophenyl)acrylate in 12.0 ml of methanol, and the mixture was stirred in a closed vessel in a microwave oven at 110 C. for 4 h. The solvent was removed under reduced pressure, the residue was taken up in dichloromethane and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 0.838 g (43% of theory) of methyl 4-cyano-3-(2,6-difluorophenyl)-4-(3,4-difluorophenyl)butanoate as diastereomer mixture (erythro:threo=54:46, integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.57 ppm and 3.61 ppm).

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; Bayer Intellectual Property GmbH; Jakobi, Harald; Mosrin, Marc; Gatzweiler, Elmar; Haeuser-Hahn, Isolde; Heinemann, Ines; Rosinger, Christopher Hugh; Schnatterer, Stefan; US2014/87945; (2014); A1;,
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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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 67515-59-7

A solution of 1.1 g (5.9 mmol) of 4-fluoro-3-trifluoromethylbenzonitrile and 485 mg (6.5 mmol) of (S)- (+)-2-BUTANOL in 10 mL of THF AT-10C was treated with 235 mg (5.9 mmol) of sodium hydride. The resulting mixture was stirred cold for 2 h, then quenched with 10 mL of H2O. The quenched solution was extracted with 30 mL of Et20, dried over MGS04 and concentrated. Chromatography on a Biotage 40M cartridge using 4: 1 v/v hexanes/Ethyl acetate as the eluant afforded 550 mg of the title compound : 1H NMR (500 MHz) 5 0.99 (t, J= 7.6, 3H), 1.35 (d, J= 6.2, 3H), 1.58-1. 83 (m, 2H), 4. 51 (septet, 1H), 7.04 (d, J= 8.7, 1H), 7.75 (d, J= 8.7, 1H), 7.85 (s, 1H).

The synthetic route of 67515-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/32465; (2005); A2;,
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