Category: nitriles-buliding-blocks

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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Aminoacetonitrile hydrochloride

To 2g (5.3mmol) C4 was added 4.42 ml (32mmol) triethylamine, 0.98g (10.6mmol) aminoacetonitrile hydrochloride, 1.22g (6.6mmol) EDCI, and 860 ml (6.6mmol) HOBT. It was dissolved in 20mL DMF. After reacting at room temperature overnight, concentrate to dry, by adding dichloromethane, with saturated sodium bicarbonate solution, salt water after washing, concentrating, methanol used for recrystallization to obtain the yellow solid, yield 90%.

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; China Pharmaceutical University; Wang, Peng; Gu, Yueqing; Huang, Jinxin; (9 pag.)(2016);,
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Application of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

Step D. 2-[1-(2-Cyano-4-nitro-phenyl)-piperidin-4-yl]-N-ethyl-2-phenyl-acetamide. To a solution of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (500 mg, 2 mmol) and 2-fluoro-5-nitro-benzonitrile (337 mg, 2.03 mmol) in DMF was added K2CO3 (840 mg, 6.1 mmol). The solution was heated to 80 C. for 16 h. After cooling to rt, H2O and 3:1 EtOAc/hexanes were added. The organic portion was washed three times with H2O and once with brine, dried (Na2SO4) and concentrated to provide the title compound (yellow powder, 686 mg, 86%).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); A1;,
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Electric Literature of 57381-41-6, A common heterocyclic compound, 57381-41-6, name is 2,5-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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.

The 5.00g (19.16mmol) 2,5- dibromobenzene cyanide, 24g (76.65mmol) 1- (4- methoxybenzyl) pyrazole boronic ester, 11.64g (76.65mmol) of cesium fluoride, 1.11g ( 0.96 mmol) tetrakis (triphenylphosphine) palladium, ethylene glycol dimethyl ether was added to 300mL 500mL three bottles, sealed, vacuum, nitrogen atmosphere, for 6 hours at 100 .After stopping the reaction, extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure, purified by silica gel column chromatography purification, 2,5-bis (1- (4-methoxybenzyl ) lH-pyrazol-4-yl) benzyl cyanide 6.5g, yield 71.33%.

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 industry university; Li, Jianrong; He, Tao; Xie, Yabo; Bai, Jinquan; (10 pag.)CN105541717; (2016); A;,
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These common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, 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. category: nitriles-buliding-blocks

[0245] A mixture of 3-fluoro-4-mtrobenzonitrile (2.85 g, 17.13 mmol), 4-(2,4- difluorophenoxy)piperidine, HC1 (3.889 g, 15.58 mmol), and ACN (19.47 mL) was heated to 80C and stirred for 12 hours, then filtered and concentrated in vacuo to afford nitro- intermediate 3-(4-(2,4-difluorophenoxy)piperidin-l-yi)-4-nitrobenzonitrile. Tlie (crude) nitro- intermediate was taken up in a 1 : 1 mixture of THF and Me OH (0.17 M, 90 mL). Ammonium chloride (12.50 g, 234 mmol) and zinc (15.28 g, 234 mmol) were added and the reaction mixture was stirred at RT for 2 hours, then filtered and concentrated in vacuo. The concentrate was diluted with water, basified with 1 M (aq) NaOH, extracted with EtOAc, dried over Na?.S04, filtered, and concentrated in vacuo to give the title compound as a viscous brown oil that solidified after 2 days (4.815 g, 94%).

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6574-99-8, name is 3,4-Dichlorobenzonitrile, 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 6574-99-8, Application In Synthesis of 3,4-Dichlorobenzonitrile

The solvent and catalyst recovered in Example 2 were used for feeding.1) In the reaction kettle with a reflux water separation device, add the anhydrous aprotic polar solvent 1,3-dimethylimidazoline used in Example 2 and make up 2000 kg with a new solvent.Raw materials 3,4-dichlorobenzonitrile 1000 kg, water agent 200 kg toluene, heated to 90 ~ 120 reflux, water separation for 1 to 2 hours, until the water in the kettle <0.05% 2) Add 800 kg of potassium fluoride and 45 kg of catalyst to the reaction kettle, raise the temperature to 130 150 , and reflux for 2 to 3 hours; 3) Turn on the vacuum pump, the vacuum degree is -0.1MPa, the top temperature of the reaction kettle tower is 90-115 C, and the toluene is collected, and the fractions are collected; 4) Continue to increase the temperature. When the temperature in the reactor reaches 190 200 and the top temperature reaches 170-180 , the crude 3,4-difluorobenzonitrile will be collected. When the content of 3,4-difluorobenzonitrile in the reactor is at At 89.0-89.5%, the reaction is deemed complete and the crude product is 818 kg; 5) Turn off the hot oil pump, turn on the cold oil system, the temperature in the reaction kettle drops below 100 C, put the materials in the reaction kettle into a centrifuge, the filtrate is pumped into the reaction kettle for the next feeding, and the solid materials are bagged; 6) The crude product 3,4-difluorobenzonitrile is drawn into the rectification kettle, stirring is started, and the fractions of 179-181 C are collected at elevated temperature and pressure to obtain the finished product 3,4-difluorobenzonitrile 743 kg, content 99.63%, yield 93.0%; after distillation, the residual liquid is sent to the reactor for the next feeding. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Dichlorobenzonitrile, and friends who are interested can also refer to it. Reference:
Patent; Ji’ning Kangsheng Rainbow Biological Technology Co., Ltd.; Qian Jidong; Huang Dingqian; Sheng Rui; Yan Weiwei; (8 pag.)CN110804001; (2020); A;,
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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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C3H7ClN2

Example 109(4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(chloromethyl)-4-(3-fluorophenyl)oxazolidin-2- one; [00174] To a solution of the mesylate, prepared using the methods described in example34 (35 mg, 0.07 mmol) and triethylamine (0.125 mL, 0.9 mmol) in DMF (0.3 mL) was added methylaminoacetonitrile hydrochloride (76 mg, 0.7 mmol). The reaction was heated to 90 ¡ãC and stirred for 3 h. After cooling, and dilution with water and ethyl acetate, the organic was washed successively with 1 M HCl, brine, dried over magnesium sulfate, filtered and concentrated. HPLC purification (0-90percent acetonitrile/water) gave 16 mg (53percent) of the title compound as a colorless oil. 1H NMR (acetone-d6) delta (ppm) 7.52-7.56 (m, 2H), 7.47 (ddd, IH, J = 8.1, 8.1, 6.0 Hz), 7.31-7.42 (m, 4H), 7.10-7.15 (m, IH), 6.95-6.99 (m, 4H), 5.55 (d, IH, J = 4.8 Hz), 4.75 (q, IH, J = 4.4 Hz), 4.10-4.17 (m, 2H). HPLC-MS calculated C22Hi6Cl2FNO3 (M+H+): 432.1, found: 432.1.

The synthetic route of 25808-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/76754; (2008); A2;,
Nitrile – Wikipedia,
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Application of 2338-75-2, These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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.

A solution of Intermediate 6a (2.0 g, 10.8 mmol) and carbon disulfide (0.71 mL, 11.8 mmol) in tetrahydrofuran (30 mL) is added dropwise to an ice cold solution of sodium hydride (950 mg of 60 % suspension in oil, 24 mmol) in tetrahydrofuran and stirred at room temperature for 3 hours. The mixture is cooled to 0 C, then methyl iodide (1.5 mL, 24 mmol) is added dropwise and stirred at room temperature for 12 hours. The mixture is poured into water andextracted with dichloromethane (2 x). The organic layers are combined, washed with brine, dried over MgSO4, filtered, concentrated and the crude material is purified by flash chromatography (hexanes/ethyl acetate gradient) to afford 3,3-bis(methylthio)-2-(4-(trifluoromethyl) phenyl)acrylonitrile I-14a.

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Azimioara, Mihai; Alper, Phil; Cow, Christopher; Mutnick, Daniel; Nikulin, Victor; Lelais, Gerald; Mecom, John; McNeill, Matthew; Michellys, Pierre-Yves; Wang, Zhiliang; Reding, Esther; Paliotti, Michael; Li, Jing; Bao, Dingjiu; Zoll, Jocelyn; Kim, Young; Zimmerman, Matthew; Groessl, Todd; Tuntland, Tove; Joseph, Sean B.; McNamara, Peter; Seidel, H. Martin; Epple, Robert; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5478 – 5483;,
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Reference of 6629-04-5,Some common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, molecular formula is C6H8N2O3, 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.

A solution of compound Al (3. 12g) and potassium carbonate (2.75g) in DMF (5OmL) is stirred at room temperature for 2 hours. 2.6mL carbon disulfide is added to the reaction suspension, and then kept stirring for 4 hours. After completion of the reaction, 100% ethanol is added to reaction mixture at 0C. Yellow precipitate is generated and filtered out. After washing with diethyl ether and drying under reduced pressure overnight, pale yellow solid, compound A2 is obtained in a yield of 92.3%. 1H-NMR (400MHz, DMSO-d6) 5 (ppm):14.92 (C3NHC4, s, 1H), 3.99 (C2H, q, J = 4.72Hz, 2H), 1.16 (C1H, t, J =4.72Hz, 3H). 13C- NMR (600MHz, DMSO-d6) 5 (ppm): 222.21 (C7), 164.35 (C4), 152.08 (C3), 125.16 (C6), 97.80 (C5), 59.09(C2), 14.50 (C1). HRMS (ESI) mlz calculated for C7H6N2O3S2K2+H308.9 172, found 308.9171. Formula is confirmed as C7H6N20352K2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Cyanoacetylurethane, its application will become more common.

Reference:
Patent; RHODE ISLAND HOSPITAL; CHEN, Qian; YU, Hongchuan; CHEN, Yupeng; (123 pag.)WO2016/81522; (2016); A1;,
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Synthetic Route of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: K2CO3, KOH and TBAB were added to a solution of each triazole compound (7a-c) in ACN. Each solution was stirred for 30 min at room temperature; alkyl bromide was added, and the reaction proceeded for 3-24 h at room temperature. The solid was filtered and then washed with diethyl ether. The solvent of the filtrate was removed in vacuo and purified by silica gel column chromatography (hexane/ethyl acetate) to yield the desired compound or crude mixture, which were reacted in the next step of deprotection.

The synthetic route of 6-Bromohexanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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Electric Literature of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

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; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts