Category: nitriles-buliding-blocks

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

General procedure: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether). 4.1.1.1. 5-Bromo-2-(isobutyl(methyl)amino)-benzonitrile (2a).Yellow oil (yield: 93%); 1H NMR (400 MHz, CDCl3) d 7.54 (d, 1H,J 1.3 Hz, ArH), 7.42 (dd, 1H, J 9.1, 3.3 Hz, ArH), 6.75 (d, 1H,J 9.1 Hz, ArH), 3.19 (d, 2H, J 7.5 Hz, -NCH3CH2CH(CH3)2), 3.05 (s,3H, -NCH3CH2CH(CH3)2), 2.01 (m,1H, eNCH3CH2CH(CH3)2), 0.89 (d,6H, J 6.6 Hz, eNCH3CH2CH(CH3)2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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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;,
Nitrile – Wikipedia,
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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;,
Nitrile – Wikipedia,
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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;,
Nitrile – Wikipedia,
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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 179898-34-1 as follows. 179898-34-1

Example 1; 3-fluoro-5-{5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridin-2-yl}benzonitrile; Step 1: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; 3-Bromo-5-fluorobenzonitrile (30.0 mmol, 9.23 g), bis(pinacolato)diboron (30.0 mmol, 7.62 g), PdCl2(dppf)2 (1:1 complex with dichloromethane, 1.2 mmol, 980 mg), and potassium acetate (105 mmol, 10.3 g) were combined in deoxygenated dioxane (150 mL) and heated at 80 C. for 4 hrs, at which time the reaction was determined to be complete by GC/MS analysis. The reaction was cooled to room temperature, and poured in to a separatory funnel containing EtOAc (300 mL) and water (200 mL). The aqueous layer was back extracted with EtOAc (75 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was carried on to the next step with out further purification or characterization.

According to the analysis of related databases, 179898-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cosford, Nicholas D.; Seiders, Thomas J.; Payne, Joseph; Roppe, Jeffrey R.; Huang, Dehua; Smith, Nicholas D.; Poon, Steve F.; King, Chris; Eastman, Brian W.; Wang, Bowei; Arruda, Jeannie M.; Vernier, Jean-Michel; Zhao, Xiumin; US2009/203903; (2009); A1;,
Nitrile – Wikipedia,
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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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1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, 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. 1835-65-0

General procedure: In the synthesis of Example 1 (1) The compound (4-1), except that a beta-naphthol(compound (a-1)), a 2,4,6-trimethyl-thiophenol (Compound (a-2)) It is to obtain a compound (4-2) in the same manner (yield: 68.1percent).

Statistics shows that 1835-65-0 is playing an increasingly important role. we look forward to future research findings about 3,4,5,6-Tetrafluorophthalonitrile.

Reference:
Patent; Yamada Kagaku Kogyo Corporation; Satoshi, Hayashi; Yosuke, Manabe; (47 pag.)KR2016/40133; (2016); 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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts