Month: December 2020

179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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. 179897-89-3

5-bromo-2-fluorobenzonitrile (1.0 g, 5.0 mmol) was weighed and dissolved in DMF (10 mL), Add K2CO3 (2.1 g, 15.0 mmol), stir at room temperature for 1.0 h, add N-methylisobutylamine (1.3 g, 15.0 mmol), and react at 80 C for 3 h. TLC followed the reaction completely.Cooled to room temperature, diluted with 100mL of water was added, ethyl acetate (100mL ¡Á 3). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, purification by silica gel column (V ethyl acetate: V petroleum ether = 1: 20) afforded 5-bromo-2-isobutylmethylaminobenzonitrile (a10)1.27 g, yield 95%

Statistics shows that 179897-89-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; South China University of Technology; Li Jing; Li Xiaolei; Li Yuanyuan; Zhou Haiyan; Zhang Lei; Guan Su; (21 pag.)CN110078668; (2019); A;,
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6393-40-4, 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 6393-40-4 as follows.

A sample of 2 (6.13 mmol) was suspended in 55 mL ofdry methanol and the suspension was saturated with HCl(g)for 30 min. After 4 days stirring at room temperature, thesuspension was filtrated and the solid was washed with120 mL of ethyl ether. The yellow solid obtained wasdissolved in dry methanol and saturated with NH3 during6 h. The solution was concentrated to half and to theresulting solution was added 60 mL of ethyl ether. Theresulting precipitated was collected by filtration and washedwith 50 mL of ethyl acetate, affording the interest product. 4-Amino-3-nitrobenzamidine hydrochloride (3) This product was obtained as a yellow solid (60%yield); mp > 300 C; IR (ATR) nu / cm-1 3453, 3420 (NH2),3134, 3052 (NH.HCl amidine), 1685 (C=N), 1628 (NH2);1H NMR (200 MHz, DMSO-d6) delta 9.38 (br s, 2H, Hamidine), 9.12 (br s, 2H, H amidine), 8.62 (s, 1H, H arom.),8.17 (s, 2H, NH2), 7.87 (d, J 9.0 Hz, 1H, H arom.), 7.19 (d,J 9.0 Hz, 1H, H arom.); 13C NMR (50 MHz, DMSO-d6) delta 163.5, 149.1, 133.6, 129.6, 127.6, 119.4, 113.2.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; de Souza, Thiago B.; Oliver, Josidel C.; Gomes, Ana Paula B.; Aragao, Cicero Flavio S.; Ferreira, Leandro S.; Nogueira, Fernando Henrique A.; Dias, Amanda Latercia T.; Alves, Ricardo J.; Journal of the Brazilian Chemical Society; vol. 29; 6; (2018); p. 1304 – 1317;,
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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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., 6011-14-9

General procedure: 2-Aminoacetonitrile hydrochloride 2 (7.0 mmol) and sodium acetate (8.0 mmol) were dissolved in 35 mL of methanol. Aldehyde 1 (7.0 mmol) was added to the grey solution, and the reaction mixture was stirred at room temperature. A solid suspension was formed after a few minutes (for compounds 3a, 3c, 3f and 3g). The suspension was stirred for 2 h and the solid filtered and washed with cold methanol, leading to the pure product 3. A second crop was isolated from the mother liquor after complete removal of methanol in the rotary evaporator, addition of dichloromethane (40 mL) and dry flash chromatography of the solution using dichloromethane (4¡Á10 mL) as eluent. The solution was concentrated in the rotary evaporator and the yellow oil was kept at 0 C leading to the product 3 that was filtered and washed with cold diethyl ether. For compounds 3b, 3d, 3e and 3h-k, the reaction mixture was stirred at room temperature for 2 h. The solvent was removed in the rotary evaporator and dichloromethane (40 mL) was added to the mixture. Dry flash chromatography of this mixture was performed using 20 mL of dichloromethane as eluent. The solvent was removed in the rotary evaporator leading to a solid product. Cold diethyl ether was added to the suspension, kept for a few minutes in an ice bath. The solid was filtered and washed with cold diethyl ether, leading to the pure (arylideneamino)acetonitrile 3.

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; Costa, Marta; Proena, Fernanda; Tetrahedron; vol. 67; 10; (2011); p. 1799 – 1804;,
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143879-80-5, 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. 143879-80-5, name is 2,3,4-Trifluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,3,4-trifluorobenzonitrile (3 g, 19 mmol), tert-butyl carbazate (4 g, 30 mmol) and Hunig’s base were dissolved in dioxane (10 mL) and heated at 100 C. for 3 d. The mixture was concentrated and then partitioned between toluene (25 mL) and water (29 mL). The toluene layer was added to a column and chromatographed (silica gel, 10 to 40% ethyl acetate in hexanes) to give product as an oil. Recrystallization from ethyl acetate/hexanes gave N’-(4-cyano-2,3-difluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.16 g, 22%) as a white powder. A second crop (0.5 g, 10%) was obtained as a slightly pinkish powder. LCMS (m/z): M+H=170.1 (loss of BOC).

The synthetic route of 2,3,4-Trifluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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16588-02-6, The chemical industry reduces the impact on the environment during synthesis 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

In order to prepare a reaction mixture, a diselenide compound represented by a general formula R?-CH2—-a solvent, and a reducing agent were prepared. As the diselenide compound represented by the general formula R??-CH2-Se-Se–CH2—R? of the reaction mixture, various substances such as (SeCH2COOEt)2? (p-NO2PhCH2Se)2, (p-CNPhCH2Se)2, and the like were used. The diselenide compounds were as shown in [Table 1]. About 0.6 eq. of the diselenide compound was used. As the solvent, anhydrous dimethylformaldehyde (DMF) was used. Further, as the reducing agent, about 0.6 eq. of dithiothreitol (DTT) was used.10291] To be specific, the reaction mixture was prepared by adding the diselenide compound represented by the general formula R?CH2Se-Se-CH2—-R? and the reducing agent to 2 mL of the solvent. The reaction mixture was stirred for 1 hour at a constant temperature of 60 C.10292] After the reaction mixture was prepared, an aromatic compound as a starting material for producing the selenophene-fused aromatic compound was added to the reaction mixture at a time. Then, the reaction mixture was stirred for 30 minutes at a constant temperature of 60 C.10293] As the base to be added afier the starting material is added to the reaction mixture with stirring, a weak base K2C03 was used. 2.5 eq. of the base was added to the reaction mixture at room temperature with stirring for 24 hours at a constant temperature of 60 C.10294] After the base was added and the stirring was finished, it was observed that the starting material was completely consumed by using a thin layer chromatography in a mixture of ethyl acetate:hexane (EA:Hex). The solvent contained in the reaction mixture was removed in a vacuum, and a crude solid was extracted 3 times by using about 25 mE of a solvent including dichloromethane:water (1:1). An organic phase collected through the extraction process was dried in an anhydrous environment by using MgSO4, and the solvent was evaporated in a vacuum. The residue was refined by column chromatography using a silica gel column. A pure product, i.e. the selenophene-fused aromatic compound produced in the present Example, was eluted by using ethyl acetate and hexane, and recrystallized by using methanol and then filtered.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samsung Life Public Welfare Foundation; Industry-Academia Cooperation Group of Sejong University; Lim, Dongyeol; Nam, Do-Hyun; Dubey, Rashmi; Lee, Hangeun; US2014/213790; (2014); A1;,
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1885-38-7, 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. 1885-38-7, name is (E)-Cinnamonitrile, A new synthetic method of this compound is introduced below.

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

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; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
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5653-62-3, A common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.

To a stirred solution of 2,3-dimethoxybenzonitrile (25)(5.0 g, 30 mmol) in Et2O (12.5 mL) under N2 atmosphere was added methylmagnesium bromide (37% in Et2O) (12.5 mL, 37 mmol). The mixture was stirred for 16 h, and then 50% AcOH (20 mL) was added. After it was stirred for 30 min, the solution was poured into crushed ice, extracted with CH2Cl2, washed with 10% Na2CO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1) to give 26. Liquid; yield: 92.5%; 1H-NMR (CDCl3, 200 MHz): delta 2.56 (s, 3H), 3.82 (s, 3H), 3.85 (s, 3H), 6.99-7.02 (m, 2H), 7.13-7.18 (m, 1H); 13C-NMR (CDCl3, 50 MHz): delta 31.18, 55.98, 61.29, 115.83, 120.80, 123.94, 133.62, 148.63, 153.04, 200.26; Anal. calcd for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.60; H, 6.73.

The synthetic route of 5653-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Efficient Pharma Management Corporate; US2012/15908; (2012); 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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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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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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