Month: February 2021

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 90433-20-8, name is 2-(3-Bromophenyl)-2-methylpropanenitrile, 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 90433-20-8, Recommanded Product: 2-(3-Bromophenyl)-2-methylpropanenitrile

General procedure: To a mixture of compound 5 (2.00 g, 12.3 mmol), X-Phos (0.292 g, 0.613 mmol), sodium tert-butoxide (2.94 g, 30.6 mmol) and tris(dibenzylidineacetone)dipalladium (0.224 g, 0.245 mmol) in 1,4-dioxane (25 mL) was added 4-bromoanisole (1.6 mL, 12.9 mmol) and heated to 100 C for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and concentrated in vacuo. The residue was powdered from diethyl ether to give the title compound (2.02 g, 61%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3-Bromophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Mochizuki, Michiyo; Kori, Masakuni; Kono, Mitsunori; Yano, Takahiko; Sako, Yuu; Tanaka, Maiko; Kanzaki, Naoyuki; Gyorkos, Albert C.; Corrette, Christopher P.; Aso, Kazuyoshi; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4675 – 4691;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 691877-03-9, name is 3-Bromo-5-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Bromo-5-(trifluoromethyl)benzonitrile

43-2 (50 mg, 0.200 mmol) was dissolved in THE (1 mL) before 1M Borane in THF (1 ML) was added. The mixture was stirred at RT overnight before concentrated IN VACUO. The residue was redissolved in a solution of 1% HCl (4N in dioxane) in methanol and heated at 50 C overnight. Solvent was stripped off and redissolved in 1% HCl in methanol. This process was repeated three times to get ride of excess borane and yield crude 43-3 (50 mg, 98.4%). LC-MS: MW calculated 252.97, found 253.8.

According to the analysis of related databases, 691877-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2004/41279; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 60899-34-5, 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. 60899-34-5 name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, 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.

(S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l-ylidene]-2-methylpropane-2- sulfinamide: To a solution of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in Toluene (60 mL) was added (S)-2-methylpropane-2-sulfinamide (4.24 g, 34.98 mmol, 1.10 equiv), Ti(OEt)4 (10.75 g, 47.15 mmol, 1.48 equiv). The resulting solution was stirred for 16 h at 60 C. The resulting solution was used directly in the next step without further purification. LC-MS: m/z = 261 [M+H]+. To a solution of l -oxo-2,3-dihydro-lH-indene-4-carbonitrile (5 g, 31.81 mmol, 1.00 equiv) in toluene (50 mL) was added (S)-2-methylpropane-2-sulfinamide (4.6 g, 37.95 mmol, 1.20 equiv), Ti(OEt)4 (1 1 g, 1.50 equiv). The resulting solution was stirred for 18 h at 60 C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of sat. potassium sodium tartrate (30 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined, washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 5.5 g (66%) of (S)-N-[(lZ)-4-cyano-2,3-dihydro-lH-inden-l -ylidene]-2- methylpropane-2-sulfinamide as a yellow green solid. LC-MS: m/z = 261 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts