Tag: M.W=100-200

10406-25-4, 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below.

Pyridin-3-ylmethanol (0.546 g, 5 mmol) in THF (2ml) was added to a suspension of 1 , 1 ‘-carbonyldiimidazole (0.81 1 g, 5.00 mmol) in THF (8ml) at 10 C. The mixture was stirred for 1 h at rt. The resultant solution was added to the solution of 4-(aminomethyl)benzonitrile (0.661 g, 5.00 mmol), DBU (0.754 ml_, 5.00 mmol), and Et3N (0.697 ml_, 5.00 mmol) in THF (10 ml). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure, and the residue was partitioned between EtOAc and water. The organic layer was separated, washed with water and brine, dried over MgS04, filtered, and concentrated under reduced pressure. The residue was recrystallized in EtOAc/hexanes to afford the title compound as a white solid (0.85 g, 63%). 1H NMR (400 MHz, DMSO-d6) delta 8.62 (s, 1 H), 8.57 (d, J = 3.91 Hz, 1 H), 8.03 (t, J = 5.87 Hz, 1 H), 7.75 – 7.89 (m, 3H), 7.40 – 7.52 (m, 3H), 5.12 (s, 2H), 4.32 (d, J = 6.07 Hz, 2H). LCMS: fR = 0.44 min, 88%.. MS (ESI): m/z 268 (M+H)+.

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; GLAXOSMITHKLINE LLC; TEMPERO PHARMACEUTICALS, INC.; GHOSH, Shomir; LOBERA, Mercedes; TRUMP, Ryan, Paul; ZHANG, Cunyu; CHEN, Peiling; WO2013/66835; (2013); A2;,
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327056-73-5, These common heterocyclic compound, 327056-73-5, name is 3-Chloro-5-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.

3-chloro-5-(3-chloro-5-methoxyphenoxy)benzonitrile(B-3); A mixture of 1.00 g (6.31 mmol) of 3-chloro-5-methoxyphenol (B-1), of 1.28 g (8.20 mmol) 3-fluoro-5-chlorobenzonitrile (B-2), and 2.62 g (18.93 mmol) of potassium carbonate in 10 mL of N-methylpyrrolidinone was heated at 120 C. in a nitrogen atmosphere with vigorous stirring. After 6 hours, LC/MS analysis indicated that the reaction was complete. The reaction was cooled to room temperature and filtered, and the solid washed with EtOAc. The filtrate was diluted further with EtOAc, and was washed with 20 mL of 1N HCl, 20 mL of 1 N NaOH, 20 mL of water, and 20 mL of brine. The organic layer was dried (anhydrous MgSO4), filtered, and the filtrate concentrated in vacuo to an orange oil. The oil was purified by flash column chromatography over silica gel with 3:1 cloroform/hexanes to give the desired product B-3 as a clear oil. MS: M+1=295. 1H NMR(CDCl3): 3.81 delta(s, 3H), 6.44 m, 1H), 6.62 (m,1H), 6.78 (m,1H), 7.14 (m,1H), 7.22(m,1H), 7.37(m,1H).

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 327056-73-5.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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 591769-05-0, 591769-05-0

3.0g of compound 9 and 2.9g of compound 5a were dissolved in 150mL acetonitrile. To the above solution, 0.10g of 1,8-diazabicyclo undec-7-ene was added and reacted at 65¡ãC for 2 days. TLC was used to determine reaction completion. After distilling off the solvent, it was dissolved in ethyl acetate then water and aqueous citric acid solution was added. 100mL saturated sodium chloride solution was washed 3 times each. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by column chromatography (methylene chloride/methanol 80:1) to give 2.4g of intermediate 10a as a white solid, yield: 48percent.

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

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
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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. 14618-78-1 name is 4,4-Dimethoxybutanenitrile, 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. 14618-78-1

In a 500 ml four-necked flask,Add 60 grams of DMF,13.0 g (0.1 mol) of 4,4-dimethoxy-n-butyronitrile,10.0 g (0.11 mol) of 2,3-difluoropropenal,0.8 g DBU, reacted at 80 C for 5 hours,The gas phase detection 1,4-addition reaction is completed.Cool down to 25-30 C,Add 10.0 grams of potassium carbonate,22.0 grams of 17% ammonia,10.0 g of ammonium chloride,Reaction at 80 C for 4 hours,Cool down to 20-25 C,filter,20 grams of ice water wash filter cake,dry,Obtained 11.4 g of 5-fluoro-7-azaindole,Liquid phase purity is 99.2%,The yield was 83.8%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4-Dimethoxybutanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Zhang Mingfeng; Wang Sheng; Li Guangqian; Ju Lizhu; (7 pag.)CN110128421; (2019); A;,
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40497-11-8, 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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask. The prepared diazonium salt solution was dropped into the flask. The reaction was complete for 2 h. Adding aqueous ammonia, adjust the pH to 9-10. Reaction at room temperature for 2h. After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2 x 30 mL), washed with saturated sodium chloride solution (1 x 40 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1.60 g of product, yield 65.3%.

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

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Guan, Xilin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (14 pag.)CN105601632; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 4640-66-8, name is 4-Chlorophenacylcyanide, 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 4640-66-8, 4640-66-8

Add Na2CO3 (0.25 mmol) to a 25 mL reaction flask,a compound (0.5 mmol) represented by the formula i1,a compound of formula m2 (0.5 mmol) and acetonitrile (3 mL),The reaction was carried out at 90 C for 24 h, and the reaction was followed by thin layer chromatography.After the reaction was completed, the solvent was evaporated under reduced pressure and ethyl acetate was dissolved.Separation on a silica gel column (developing solvent petroleum ether / ethyl acetate volume ratio = 6:1) afforded white solid compound A14.(The structural formula of the compound A14 is as shown by n3,The synthesis reaction formula is shown in Fig. 26, and the yield was 68%).

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

Reference:
Patent; Anhui Normal University; Li Qianqian; He Xinwei; Tao Jiajia; Shang Yongjia; (26 pag.)CN108440467; (2018); A;,
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4110-35-4, 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. 4110-35-4, name is 3,5-Dinitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1.1.62: 5-(aminomethyl)-Nl, N l,N3,N3-tetramethylbenzene- 1,3 -diamine; 20% Pd(OH)2 (0.13 g) was added to a stirred suspension of 3,5-dinitrobenzonitrile (0.50 g, 2.59 mmol, 1 eq, Aldrich) in 10 ml EtOH. A H2 balloon was added. After stirring over the weekend the mixture was filtered through Celite. The filter cake was rinsed with EtOH (x3). The organics were removed in vacuo. The residue was stirred in CHCl3 and the resulting mixture was filtered (x3). The CHCl3 fractions were combined, and the solvent was removed in vacuo to yield crude 3,5-diaminobenzonitrile.

The synthetic route of 4110-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
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25808-30-4, 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below.

EXAMPLE 8 3-Amino-1,4,5-trimethyl-1H-pyrrole-2-carbonitrile 10.3 ml (0.74 mole) of triethylamine, 7.2 g (0.74 mole) of 3-cyanobutan-2-one and 0.5 g of p-toluenesulfonic acid are successively added to a suspension of 7.8 g (0.74 mole) of N-methylaminoacetonitrile hydrochloride in 70 ml of chloroform, and the mixture is boiled for 5 hours, using a water separator. After it has been boiled, the mixture is washed twice with 10 ml of water each time and dried over sodium sulfate; the solvent is then stripped off in vacuo. In order to remove all of the chloroform, the residue is twice taken up in 100 ml (each time) of dry ethanol, and the mixture concentrated each time in vacuo. The resulting oil is warmed (bath temperature of 50¡ã C.) in 100 ml of 1 N sodium ethylate/ethanol for 2 hours; some of the ethanol is removed. The mixture is then taken up in 100 ml of water and extracted several times with methylene chloride. After being dried over sodium sulfate and concentrated on a rotary evaporator, the extracts yield a solid residue, which is recrystallized from diisopropyl ether.

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; BYK Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4363816; (1982); A;,
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6136-68-1, 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. 6136-68-1, name is 3-Acetylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred mixture of SeO2 (20 mmol, 2.2 g) in dioxane (20 mL) was added water (2 mL) and heated toreflux until SeO2 was dissolved. Compound 1a (10 mmol, 1.45 g) was added and the mixture wasstirred at reflux overnight. After completion, the mixture was filtered through a pad of celite. Thefiltrate was concentrated in vacuo. Compound 3-(2-oxoacetyl)benzonitrile was obtained and useddirectly in next step without further purification. To a suspension of alpha-aminoacetamide hydrochloride(1.5 g, 14 mmol) in MeOH (12.5 mL)-water (3.1 mL) was added 12.5 M aqueous NaOH (1.65 mL, 20mmol) solution at -30 C, and then a solution of NaOH (543 mg, 14 mmol) in MeOH (6.1 mL) wasadded to the mixture. A solution of 3-(2-oxoacetyl)benzonitrile in MeOH (11.1 mL) was added to themixture at -20C, and then the resulting suspension was stirred for 2h at same temperature, and thestirring continued for 1 h at room temperature. After cooling with ice water, the mixture was acidifiedwith AcOH. Collection of the resulting precipitates by filtration gave 2a (52%) as a red solid:

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; Zhang, Niu-niu; An, Bai-jiao; Zhou, Yan; Li, Xing-shu; Yan, Ming; Molecules; vol. 24; 6; (2019);,
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332-25-2, 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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, A new synthetic method of this compound is introduced below.

Step A: Anhydrous CeCl3 (0.84 g, 3.4 mmol) was stirred in dry THF (10 mL), at room temperature, under a N2 atmosphere for 2 h. Then, the solution was cooled at -78 ¡ãC, followed by dropwise addition of MeLi (2.2 mL, 3.4 mmol, 1.6 M), and allowed to stir for 30 min at -78 ¡ãC. Then, a solution of 4-methoxybenzonitrile (0.15 g, 1.1 mmol) in dry THF (5 mL) was added dropwise to the above solution. The crude reaction was stirred at room temperature overnight, quenched by adding 1.5 mL of concentrated NH4OH, and allowed to stir for 1 h at room temperature. The organic layer was filtered, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was used for next reaction without further purification.

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; Gallardo-Macias, Ricardo; Kumar, Pradeep; Jaskowski, Mark; Richmann, Todd; Shrestha, Riju; Russo, Riccardo; Singleton, Eric; Zimmerman, Matthew D.; Ho, Hsin Pin; Dartois, Veronique; Connell, Nancy; Alland, David; Freundlich, Joel S.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 601 – 606;,
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