Category: nitriles-buliding-blocks

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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 67832-11-5

30Step A: 4-bromo-2-ethylbenzonitrile A solution of 4-bromo-2-methylbenzonitrile (4.00 g, 20.4 mmol) in THF (40 mL) was addeddropwise to a solution of lithium diisopropylamide (2.0 M in THF, 16 mL, 32.0 mmol) in THF(10 mL) over a period of 20 mm at -78 C under nitrogen atmosphere. After 2 h, iodomethane(3.48 g, 24.5 mmol) was added dropwise over a period of 20 mm at the same temperature. Thereaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture wasre-cooled to 0 C and acidified with 1 M hydrochloric acid to pHi. The aqueous layer was extracted with ethyl acetate several times. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was then purified by flash chromatography on a silica gel column using 0-10% ethyl acetate/petroleum ether as theeluting solvents to give the title compound. ?H NIVIR (400 MHz, CDC13) 7.46 (s, 1H), 7.44-7.35 (m, 2H), 2.81 (q, J 7.7 Hz, 2H), 1.26 (t, J= 7.6 Hz, 3H).

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 67832-11-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SUZUKI, Takao; VACCA, Joseph P.; PU, Zhifa; XU, Shouning; PASTERNAK, Alexander; DAVIES, Ian; DING, Fa-Xiang; JIANG, Jinlong; DONG, Shuzhi; GU, Xin; (0 pag.)WO2016/8064; (2016); 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, category: nitriles-buliding-blocks

0.15g of compound 3 and 0.14g of compound 5a were dissolved in 30mL acetonitrile. To the above solution, 0.10g of 1,8-diazabicyclo undec-7-ene was added and reacted at 65¡ãC for 5-6 days. 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 0.10g of intermediate 6a as a yellow solid, yield: 37percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyclopentylacrylonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
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Synthetic Route of 3939-09-1, The chemical industry reduces the impact on the environment during synthesis 3939-09-1, name is 2,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of NaH (1.2 g, 30 mmol) in toluene (50 mL) was added but-3-en-1-ol (1.8 g, 25 mmol) dropwise and the mixture was allowed to stir at room temperature for 30 minutes. 2,4-Difluorobenzonitrile (4.2 g, 30 mmol) was then added in one portion and the mixture was allowed to stir at room temperature for 6 hours. Water (30 mL) was slowly added and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified using flash column chromatography on silica gel (20:1 PE:EtOAc) to provide compound Int-2b (4.2 g, 78%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.51-7.53 (m, 1H), 7.20-7.25 (m, 1H), 6.79-6.81 (m, 1H), 5.85-5.89 (m, 1H), 5.05-5.11 (m, 2H), 4.05-4.11 (m, 2H), 2.47-2.51 (m, 2H).

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, 2,4-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Reger, Thomas S.; Walji, Abbas M.; Sanders, John M.; Wai, John S.; Wang, Liping; US2015/203512; (2015); A1;,
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Reference of 13338-63-1,Some common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trimethoxyphenylacetonitrile, its application will become more common.

Reference:
Article; Madadi, Nikhil R.; Penthala, Narsimha R.; Howk, Kevin; Ketkar, Amit; Eoff, Robert L.; Borrelli, Michael J.; Crooks, Peter A.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 123 – 132;,
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Application of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-trifluoromethyl-benzonitrile (453A) A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115 C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 753A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6*50 mm, eluding with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

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; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;,
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68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, 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. SDS of cas: 68119-31-3

(2,2-Difluoro-1,3-benzodioxol-5-yl)-acetonitrile (1.0 eq.), 50 wt% aqueous KOH (5.0 eq.), 1-bromo-2-chloro A mixture of ethane (1.5 eq.) and Oct 4 NBr (0.02 eq.) was heated at 70 C for 1 h. The reaction mixture was cooled and then treated with MTBE and water. The organic phase was washed with water and brine. The solvent was removed to provide (2,2-difluoro-1,3-benzodioxol-5-yl)-cyclopropanecarbonitrile.

The synthetic route of 68119-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, MARINUS JACOBUS; ALARGOVA, ROSSITZA GUEORGUIEVA; KAUSHIK, RITU ROHIT; KADIYALA, IRINA NIKOLAEVNA; YOUNG, CHRISTOPHER; (118 pag.)TWI636051; (2018); B;,
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Application of 876-31-3, The chemical industry reduces the impact on the environment during synthesis 876-31-3, name is 4-(Cyanomethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

To a stirred and ice-cooled solution of sodium methoxide (0.388 g, 7.1802 mmol) in methanol (30 ml), 4-cyanophenylacetonitrile (0.817 g, 5.7442 mmol) and 1 – azido-2,4-dichloro-benzene (0.900 g, 4.7868 mmol) are added portion wise under a nitrogen atmosphere. The reaction mixture is allowed to attain room temperature spontaneously overnight, concentrated in vacuo, added water and extracted with ethylacetate (3 x 100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to give a dark brown gummy residue (1 .425 g, 90% mass balance). This crude material is purified by column chromatography over silica gel (230-400 mesh) eluting with 20% ethylacetate in petroleum ether, to afford the title compound as a yellow solid (0.450 g, 29% yield). LC-ESI-HRMS of [M+H]+ shows 330.0319 Da. CaIc. 330.031326 Da, dev. 1 .7 ppm.

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-(Cyanomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NeuroSearch A/S; WO2009/19278; (2009); A1;,
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Synthetic Route of 1187-42-4, These common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, 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.

In a 100 mL two-necked flask, 2.6 lg (10 mmol) of 5-bromoacenaphthenequinone, 1.08 g (10 mmol) of diaminomaleonitrile, and 60 mL of acetic acid were sequentially added thereto, and the temperature was raised to 120 ¡ã C, and the mixture was stirred under reflux for 24 hours. The mixture was cooled to room temperature, poured into water, filtered under reduced pressure and washed with a large amount of water. The residue was dried and separated and purified on a silica gel column using dichloromethane: petroleum ether = 3:1 (volume ratio) eluent to obtain yellow. 3-bromoacenaphthenequinoneopyrazine-8,9-dicarbonitrile 2.44g, yield 77¡¤27percent

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Soochow University (Suzhou); Liao Liangsheng; Yuan Yi; Jiang Zuoquan; Hu Yun; (37 pag.)CN108440424; (2018); A;,
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Related Products of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

After cooling a solution of 3-oxocyclobutanecarbonitrile (32 g, 336 mmol) in methanol (330 mL) to 0 C.,NaBH4 (6.37 g, 168 mmol) was added in small portions. The mixture was stirred at 0 C. for 1 hour.The reaction mixture was quenched with saturated aqueous NaHCO 3 and extracted with ethyl acetate (800 mL).The organic layer was dried over Na2SO4, filtered,Concentrated. This procedure was repeated two more times on the same scale, combined for purification by silica gel chromatography, eluting with 10: 1 to 1: 1 petroleum ether: ethyl acetate to yield the product (30.3 g, 296 mmol, yield). 70%).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
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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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-5-chlorobenzonitrile

Step 1 Methyl 4-chloro-2-cyanophenylcarbamate A 100 mL round bottom flask was charged with 2-amino-5-chlorobenzonitrile (0.76 g, 5.0 mmol), methyl chloroformate (0.43 mL, 5.40 mmol), NaHCO3 (0.5 g, 6.0 mmol) and 2-butanone (25 mL). The resulting mixture was stirred overnight at reflux. Reaction progress was monitored by TLC (EtOAc/Petroleum ether=1:10). Work-up: the reaction mixture was filtered and the solid was washed more 2-butanone (20 mL*2). The filtrate was concentrated in vacuo, to give 0.95 g (97percent) of the product as white solid.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; Alcon Research, Ltd; US2010/120741; (2010); A1;,
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