Month: August 2021

Related Products of 368-77-4,Some common heterocyclic compound, 368-77-4, name is 3-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

Under the protection of nitrogen,To a 10 ml Schlek reaction tube (a glass apparatus commonly used in anhydrous anaerobic operation), 1.0 mmol of o-bromobenzyl alcohol, 1.3 mmol of 3-trifluoromethylbenzonitrile,0.1mmol RuH2(PPh3)4,0.1 mmol palladium acetate,0.15 mmol 1,3-bis (2,6-diisopropylphenyl) -4,5-dihydro-imidazole tetrafluoroborate,0.15mmol silver oxide,4.0mmol sodium hydride,And 5 ml of N,N-dimethylformamide,Replace the reaction tube three times with nitrogen,Then heated to 160 C with an oil bath under magnetic stirring.The reaction was refluxed for 20 hours.Remove the oil bath and lower it to room temperature;Add 3 ml of water to the reaction solution.Use 5ml of dichloromethaneAlkane extraction three times,The organic phases were combined and dried over anhydrous MgSO4 for 30 min.Filtered; the filtrate was concentrated with a rotary evaporator, the concentrated solids with dichloromethane as solvent, the product was recrystallized to give pure 11, 80% yield.

The synthetic route of 368-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lianyungang Duxiang Chemical Co., Ltd.; Xu Chen; Wang Duzheng; Xie Jianxin; Wang Chuanmin; Zheng Xiaobin; (9 pag.)CN108586342; (2018); A;,
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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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,6-Dichloro-3-nitrobenzonitrile

Example 4 Synthesis of 2-(2,6-Dichlorophenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinoline-9-one. A solution of 2,6-dichloro-3-nitrobenzonitrile (98.7 g, 0.455 mol) in EtOAc (910 mL) was cooled to 5 C. 40% Aqueous methylamine (79.5 mL, 1.14 mol) was added with vigorous mechanical stirring, keeping the temperature at 10-15 C. After addition was complete, stirring was continued for 3 h at the same temperature. More methylamine (16 mL, 0.23 mol) was added, and the mixture stirred for a further 1.5 h at room temperature. Water (300 mL) was added, followed by hexane (450 mL). The mixture was stirred for 15 min, filtered, and the solid washed with water and MeOH, to give 6-chloro-2-methylamino-3-nitrobenzonitrile (80.3 g, 83%), mp 167-170 C.

According to the analysis of related databases, 5866-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Snow, Roger John; Cardozo, Mario; Goldberg, Daniel; Hammach, Abdelhakim; Morwick, Tina; Moss, Neil; Patel, Usha R.; Prokopowicz III, Anthony S.; Takahashi, Hidenori; Tschantz, Matt Aaron; Wang, Xiao-Jun; US2002/16460; (2002); A1;,
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Electric Literature of 1885-38-7, A common heterocyclic compound, 1885-38-7, name is (E)-Cinnamonitrile, molecular formula is C9H7N, 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: To a mixture of dimethyl-3-p-tolyloxiranyl-2,2-dicarboxylate(1a, 0. 25 g, 1 mmol, 1 equiv) and benzonitrile (2a, 0.52g, 5mmol, 5 equiv) was added SnCl4 (0.12 mL, 1 mmol, 1 equiv) at 0C. The reaction mixture was then stirred at r.t. until the startingmaterials were consumed as indicated by TLC analysis. Themixture was poured into 50 mL aq sat. NaHCO3 solution andextracted with CH2Cl2 (3 × 25 mL). The combined organic layerwas rinsed with H2O, brine, and dried over anhydrous MgSO4.The solvent was evaporated off to get a residue which was thenpurified by flash chromatography to give pure product 3aa (269mg, 76%). 1H NMR (500 MHz, CDCl3): delta = 8.11 (d, J = 7.8 Hz, 2 H),7.54 (t, J = 7.5 Hz, 1 H), 7.46 (t, J = 7.5 Hz, 2 H), 7.19 (d, J = 7.9 Hz,2 H), 7.11 (d, J = 7.9 Hz, 2 H), 6.15 (s, 1 H), 3.90 (s, 3 H), 3.20 (s, 3H), 2.31 (s, 3 H). 13C NMR (125 MHz, CDCl3): delta = 167.6, 166.0,162.9, 138.2, 133.5, 132.2, 128.9, 128.9, 128.6, 128.0, 126.6,90.7, 76.6, 53.8, 52.5, 21.3. HRMS: m/z calcd for C20H19NO5 [M +H+]: 354.1336; found: 354.13302

The synthetic route of 1885-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Hai; Zeng, Xiaofei; Xie, Yan; Zhong, Guofu; Synlett; vol. 26; 12; (2015); p. 1693 – 1696;,
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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. 453565-55-4, name is 5-Fluoroisophthalonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Fluoroisophthalonitrile

5 mmol of 3,6-di-tert-butyl-9-bromocarbazole is dissolved in 2 mL of anhydrous tetrahydrofuran (THF) under a nitrogen gas range.Then add 5 mmol of sodium hydride,The mixture was stirred at room temperature for 30 minutes.Subsequently,Add 1 mmol of 1,3-dicyano-5-fluorobenzene to the reaction flask.Stirring was continued for 1 hour.Finally, 2 mL of cold water was added to the mixture to quench the reaction.After the mixture is cooled to room temperature,Vacuum filtration,The product of the reaction is then purified by column chromatography.The purified product is dried in vacuo to give the final 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:
Patent; Kunshan Guoxian Optoelectric Co., Ltd.; Tsinghua University; Duan Lian; Zhang Dongdong; Qiu Yong; Zhao Fei; Liu Song; (39 pag.)CN108264479; (2018); A;,
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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. 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrClN

Reference Example 14; 2-chloro-4-(1H-pyrazol-4-yl)benzonitrile tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.53 g), 4-bromo-2-chlorobenzonitrile (1.43 g) and triethylamine (1.45 mL) were dissolved in THF-water (6:1, 11.7 mL), and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride dichloromethane complex (1:1) (127.4 mg) was added under a nitrogen atmosphere. The reaction mixture was stirred with heating under reflux for 3 hr, and the mixture was cooled to room temperature and TFA (20 mL) was added. The reaction mixture was stirred at room temperature for 1.5 hr, and concentrated. 1 mol/L Aqueous sodium hydroxide solution was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (hexane-ethyl acetate) to give the title compound (808.6 mg) as pale-orange crystals.1H-NMR (CDCl3) delta: 7.80 (1H, dd), 7.93 (1H, d), 8.05 (1H, d), 8.22 (1H, brs), 8.44 (1H, brs), 13.27 (1H, brs).

According to the analysis of related databases, 154607-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/270359; (2009); A1;,
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These common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, 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. HPLC of Formula: C3H4N2S

General procedure: The corresponding 2-bromo-1-(aryl)ethan-1-one derivative (0.02 mol, 1 equiv.) and 2-cyanothioacetamide (0.02 mol, 1 equiv.) were dissolved in dry THF (50 mL) followed by the addition of Et3N (0.022 mol, 1.1 equiv.) (precipitation of a white solid). The reaction mixture was left to react at room temperature overnight. The solid was filtered off and the filtrate was concentrated on a rotary evaporator. The residue was dissolved in EtOAc (200 mL) and washed with water (2 50 mL), saturated aqueous solution of NaHCO3 (2 50 mL), and brine (50 mL), and dried over Na2SO4. The solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography (EtOAc:hexane, 1:8) to give the desired product (71%) as a dark yellow solid. Mp = 50-51 C. 1H NMR (400 MHz, CDCl3): delta (ppm) 4.15 (s, 2H), 7.32-7.37 (m, 1H), 7.39-7.44 (m, 2H), 7.46 (s, 1H), 7.84-7.88 (m, 2H).

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

Reference:
Article; Pajk, Stane; ?ivec, Matej; ?ink, Roman; Sosi?, Izidor; Neu, Margarete; Chung, Chun-Wa; Martinez-Hoyos, Maria; Perez-Herran, Esther; Alvarez-Gomez, Daniel; Alvarez-Ruiz, Emilio; Mendoza-Losana, Alfonso; Castro-Pichel, Julia; Barros, David; Ballell-Pages, Lluis; Young, Robert J.; Convery, Maire A.; Encinas, Lourdes; Gobec, Stanislav; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 252 – 257;,
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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. 2941-29-9, name is Cyclopentanone-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 2941-29-9

ntermediate 7f: Benzyl N-[4-[(2-cyanocyclopenten-1 -yI)-(cyanomethyl)amino]-2- fluoro-phenyl]carbamate[00242] A mixture of benzyl N-[4-(cyanomethylamino)-2-fluoro-phenyl]carbamate (4.43g, 14.7gmmol), 2-oxocyclopentanecarbonitrile (1 .62g, 14.81 mmol) and p-toluenesulfonic acidmonohydrate (0.25g, 1 .47mmol) in toluene (25mL) was heated to 150 °C with under Dean Stark conditions for 3 hours. Additional 2-oxocyclopentanecarbonitrile (1.65g, 15.l6mmol) was added and the reaction was stirred for 2 hours left at 150 °C under Dean-Stark conditions. The reaction was then cooled to room temperature and concentrated in vacuo to afford a brown oil. The brown oil was partitioned between sat. aq. NaHCO3 (5OmL) and EtOAc (5OmL). The aqueous layer was thenextracted with EtOAc (2 x 5OmL), washed with brine (3 x 5OmL), dried over Na2504, filtered and concentrated in vacuo to afford benzyl N-[4-[(2-cyanocyclopenten-1 -yl)-(cyanomethyl)amino]-2- fluoro-phenyl]carbamate as a brown oil (8.34g, 13.46mmol, 91percent yield).1H NMR (DMSO-d6, 400MHz) O/ppm: 9.64 (1H, 5), 7.77 (1H, t, J = 8.8Hz), 7.13-7.45 (7H, m), 5.17 (2H, 5), 4.84 (2H, 5), 2.59-2.63 (2H, m), 2.50-2.55 (2H, m), 1.83-1.91 (2H, m).MS Method 2: RT: 1.79 mi mlz 391.3 [M+H]

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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Electric Literature of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Cyano-4-chloroaniline. 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

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, 2-Chloro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/87575; (2004); 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Fluoro-3-nitrobenzonitrile

(a) 4-Fluoro-3-nitro-benzylamine hydrochlorideBH3/THF (120 mL; 120 mmol) was added to a solution of 4-fluoro-3-nitro-benzonitrile (10 g; 60 mmol) in THF (50 mL) over 30 min at 0 °C and the resulting mixture was stirred at 0 °C for 1 h and at rt for 3 h. The mixture was acidified to pH ~1 and stirred for 1 h at rt, basicified to pH -7-8 and extracted with EtOAc. The organic layer was dried over Na2S04, filtered and concentrated. The residue was dissolved in Et20 and treated with a solution of HCI in 1 ,4- dioxane to give the sub-title compound.Yield: 8.7 g (70percent).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; KUELZER, Raimund; MACK, Juergen; PFAU, Roland; STENKAMP, Dirk; PELCMAN, Benjamin; ROENN, Robert; LUBRIKS, Dimitrijs; SUNA, Edgars; WO2012/76672; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 98730-77-9, name is 1-(Hydroxymethyl)cyclopropanecarbonitrile, 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 98730-77-9, Computed Properties of C5H7NO

A stirred mixture of 1-(hydroxymethyl)cyclopropanecarbonitrile (24.30mmol, 2.36g) in dichloromethane (3OmL) was treated with triethylamine (48.6mmol, 6.83mL, 4.92g) and portionwise with methanesulfonyl chloride (31.6mmol, 2.445mL, 3.62g) keeping the reaction mixture at O0C. The solution was allowed to stir for 1 hour then diluted with saturated sodium hydrogencarbonate and extracted with 10% methanol/dichloromethane (x3). The organic layers were combined and concentrated under reduced pressure to give the intermediate (i-cyanocyclopropyl)methyl methanesulfonate (3.77g).1H NMR (CDCI3, 400 MHz): delta 1.18 (2H, m), 1.46 (2H, m), 3.14 (3H, s), 4.18 (2H, s)

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:
Patent; N.V. ORGANON; WO2009/24550; (2009); A1;,
Nitrile – Wikipedia,
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