Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 1246213-27-3, name is 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-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 1246213-27-3, name: 2-(2-(Benzyloxy)-5-(tert-butyl)phenyl)-2-methylpropanenitrile

To a stirred solution of compound 7 (20 g, 0.065 mol) in toluene (300 mL), was added drop wise DIBAH (80 mL, 1 M in toluene) at about -60 to -50 0C. After stirring for 2 hours, 6 N HCl (300 mL) was added to the reaction mixture and stirring was continued for 30 minutes. The organic layer was then separated, washed with 2 N HCl followed by a NaHCtheta3 solution, then a brine solution, dried over Na2SO4 and concentrated in vacuo to afford the compound 8 as an oil. The product was used in the next reaction without further purification. 1H NMR (CDCl3; 400 MHz) delta 9.61 (s), delta 7.36 (m), delta 7.25 (m), delta 6.87 (m), delta 5.06 (m), delta 1.43 (S), delta 1.33 (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; VERTEX PHARMACEUTICALS INCORPORATED; DEMATTEI, John; LOOKER, Adam, R.; NEUBERT-LANGILLE, Bobbianna; TRUDEAU, Martin; ROEPER, Stefanie; RYAN, Michael, P.; YAP, Dahrika, Milfred Lao; KRUEGER, Brian, R.; GROOTENHUIS, Peter, D.J.; VAN GOOR, Frederick, F.; BOTFIELD, Martyn, C.; ZLOKARNIK, Gregor; WO2010/108162; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 25978-68-1, 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. 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-cyano-3-methyl-benzoic acid methyl es­terfrom Example E2h.l (1.6g, 9.3mmol) in methanol (50ml) to 0C was treated with cobalt(II) chloride hexahydrate (5.1g, 18.6mmol). The mixture was stirred for 15min at room temperature then sodium borohydride (3.5g, 93mmol) was added portionwise. The reaction mixture was stirred for 90min then concentrated NH3 (5ml) was added drop-wise. The mixture was warmed up to room temperature over 30min, filtered through Celite filter agent, washed with methanol and the filtrate was concentrated in vacuo. The residue was purified by flash chromatog­raphy on silica gel (eluant; 1% 35% ammonia:10% metha­nol: 89% dichloromethane) to yield the title compound (670mg, 37%) .

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

Reference:
Patent; FERRING B.V.; WO2006/21213; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 64113-85-5, 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 64113-85-5 as follows.

2-cyanobiphenyl-4-carboxylic acid, 11 The compound 9 (1.1 g, 6.0 mmol) is dissolved in pyridine (10 mL) and water (2 mL). To this solid, KMnO4 (0.9 g, 6.0 mmol, 1 equiv.) is added, and the reaction is heated to reflux. Additional 0.25 equiv. of KMnO4 is added every 30 min. for 1O h. The reaction is further refluxed for 50 h and filtered hot and the filtrate is evaporated under reduced pressure. The residue is dissolved in 20 mL water with heating. The solution is acidified to pH 2 with cone. HCl after cooling to room temperature. The white precipitate is collected by filtration and washed generously with cold water and the product is dried under vacuum overnight. Yield 1.1 g, 86 %; mp 195-200 0C; 1HNMR (400 MHz, CDCl3) delta 2; 13CNMR (101 MHz, CDCl3) delta 2; IR (Neat, cm’1); GC-MS (EI) m/z (M+); Anal. (Ci4Hi ^0.0.75H2O) C, H, N.

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GOVERNMENT OF THE UNITED STATES OF AMERICA, REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/92072; (2008); A2;,
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. 57381-39-2, name is 2-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-5-fluorobenzonitrile

A suspension of [2-BROMO-5-FLUOROBENZONITRILE] (30.0 g, 150 mmol), bis (pinacolato) diboron (41.9 g, 165 mmol) and potassium acetate (29.4 g, 300 mmol) in 1,4-dioxane (375 ml) and DMSO (30 ml) was degassed with nitrogen for 1 h. Dichloro [[L,] [1′-BIS] (diphenylphosphino) ferrocene]- palladium (II) dichloromethane adduct (3.7 g, 4.5 mmol) was added and the mixture heated at [90C] for [18] h. The mixture was allowed to cool to ambient temperature then diluted with diethyl ether (300 ml) and filtered through a glass microfibre filter paper. The solvent was evaporated and the residue was treated with ice-cold 2N sodium hydroxide solution (250 ml) and the mixture left to stir for 15 min. The aqueous phase was extracted with diethyl ether (200 ml). The pH of the aqueous was adjusted to 5 by the addition of concentrated hydrochloric acid. The aqueous phase was extracted with diethyl ether (2 x 200 ml), the organic phase was combined, washed with water (150 ml) and brine (150 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give 5-fluoro-2- (4,4, 5, [5-TETRAMETHYL- [1,] 3,2] dioxaborolan-2-yl) benzonitrile (36.5 g, [98%)] as a brown oil which crystallised on standing: [5H] (360 MHz, CDCl3) 1.38 (12H, s), 7.25-7.30 (1H, m), 7.40 (1H, dd, J 3 and 8), 7.91 (1H, dd, J 6 and 8). 5-Fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)- benzonitrile (0.99 g, 4.0 mmol) and [1,] 3-dibromo-5-fluorobenzene (1.52 g, [6.] 0 mmol) were suspended in 1,2-dimethoxyethane (8 ml) and 2N sodium carbonate solution (4 [ML)] and degassed for 30 min before addition of tetrakis (triphenylphosphine) palladium [(0).] On complete addition the mixture was heated at [65C] for 20 h. The mixture was partitioned between ethyl acetate (100 ml) and water (50 ml), the organic layer separated and washed with brine (50 ml), dried over anhydrous sodium sulphate, filtered and evaporated onto silica. The product was purified by flash column chromatography on silica, eluting with isohexane on a gradient of diethyl ether (5-100%). Combination of the desired fractions and evaporation gave [3′-BROMO-4,] [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (110 mg, 9%) as a white solid: [SN] (500 MHz, [CD13)] 7.53-7. 55 [(1H,] m), 7.67 (1H, s), 7.69-7. 76 (3H, m), 8.03 [(1H,] dd, [J 9 AND] 2). [2- (8-FLUOROIMIDAZO [L,] 2-a] [PYRIDIN-7-YL)] propan-2-ol (58 mg, 0.3 mmol) and 3′-bromo-4, [5′-DIFLUOROBIPHENYL-2-CARBONITRILE] (106 mg, 0.36 mmol) were coupled following the procedure in Example 6 to afford 4,3′-difluoro- 5′- [8-fluoro-7- (l-hydroxy-l-methylethyl) imidazo [1, [2-A] PYRIDIN-3-YL]-] [BIPHENYL-2-CARBONITRILE] (25 mg, 20%) as a white solid: [SN] (500 MHz, [CD13)] 1.74 (6H, s), 2.07 [(1H,] s), 7.22-7. 26 (2H, m), 7.35 [(1H,] d, J 9), 7.39-7. 45 [(1H,] m), 7.51-7. 57 (3H, m), 7.76 [(1H,] s), 8.35 [(1H,] d, J 7) ; [RNLZ] (ES+) 408 (100%, [[MH] +).]

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 57381-39-2.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/99816; (2003); A1;,
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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-3-nitrobenzonitrile

To a solution of 2-chloro-3-nitrobenzonitrile (200 mg, 1 .3 mmol) in absolute THF (20 mL) was added dropwise BH3SMe2 (0.2 mL, 2.6 mmol) under nitrogen atmosphere protection. The mixture was stirred at reflux for 2 hrs. Then 2 N HCI (1 .5 mL) was added to the mixture and the mixture was stirred at reflux for 1 hour. The mixture was condensed to crude compound CI-1 -5B (248 mg) as yellow solid.

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 34662-24-3.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret; WO2013/62945; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 34662-30-1, name is 3-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-5-nitrobenzonitrile

3-Chloro-5-nitrobenzonitrile (30.0 g) was dissolved in a mixture of water (85 mL) and H2SO4 (250 mL) and heated under an N2 atmosphere at 150 C. for 2 h. The mixture was cooled to ambient temperature and poured onto ice (1 L). The resulting solid was collected by vacuum filtration, and the filtrate was extracted with ethyl acetate. The extract and solid were combined, washed with water and brine, then were dried over MgSO4, filtered, and evaporated. The residue was dissolved in 1:1 water/MeOH (200 mL) with heating, treated with decolorizing charcoal and filtered. Water (100 mL) was added and the mixture was allowed to cool and crystallize. The product was obtained as pale yellow crystals. 1H-NMR (d6-DMSO): delta 14.00 (1H, br s), 8.51 (2H, m), 8.29 (1H, m). 13C-NMR (d6-DMSO): delta 164.9, 149.2, 135.2, 135.0, 134.5, 127.7, 122.9.

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; Ashley, Gary W.; Menzella, Hugo; Wee, Janice Lau; Carney, John R.; US2008/188450; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 32446-66-5,Some common heterocyclic compound, 32446-66-5, name is 4,4′-Dicyanobenzophenone, molecular formula is C15H8N2O, 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.

4-[(4-Cyanophenyl)methanehydrazonoyl]benzonitrile (8u). To a mixture of 4-[(4- eyanophenyl)earbonyl]benzonitrile (6u) (0.56 g, 2.4 mmol) and EtOH (30 ml) hydrazine monohydrate (1.8 g, 36 mmol) was added dropwise over 5 mm. The yellow solution wasstirred overnight (about 16 h) at 80C, the mixture was allowed to cool to rt and EtOAe (150 ml) was added. The organic layer was washed with water (50 ml + 2 x 25 ml). The inorganic wash layers were extracted with EtOAe (2 x 25 ml). The organic layers were combined, washed neutral with aq. sat. NaC1 (25 ml), dried over Na2SO4 and concentrated at reduced pressure to afford a slightly red solid 8u (0.51 g, 86%).

The synthetic route of 32446-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 19295-57-9, The chemical industry reduces the impact on the environment during synthesis 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, I believe this compound will play a more active role in future production and life.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-hydroxy-2,2-dimethylpropanenitrile (10.4 g, 104.91 mmol, 3.00 equiv). This was followed by the addition of FeCl3 (566.5 mg, 3.49 mmol, 0.10 equiv) in portions. The mixture was stirred for 1 h at room temperature. To this was added 174.1 (8 g, 34.92 mmol, 1.00 equiv) dropwise with stirring at 0 C. in a water/ice bath. The resulting solution was stirred for 1 h at room temperature. The resulting solution was diluted with 200 mL of H2O. The resulting solution was extracted with 3×200 mL of MTBE and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:8). The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, Flash-C18; mobile phase, CH3CN_H2O=10:90 increasing to CH3CN_H2O=100:0 within 35 min; Detector, UV 254 nm. This resulted in 7.1 g (62%) of 174.2 as yellow oil.

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-Hydroxy-2,2-dimethylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 39263-32-6, name is 2-Amino-5-bromobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 39263-32-6

Using a literature procedure described in the following literature reference which is herein incorporated by reference in its entirety for all purposes as if fully set forth herein, a dry round bottom flask was charged with 2-amino-5-bromo benzonitrile (1 equivalent) and zinc cyanide (2 equivalents), and DMF was added: J. Med. Chem. 2000,43, 4063. Nitrogen was bubbled through the solution for 5 minutes, and Pd [P (Ph) 3] 4 was added in one portion. The reaction mixture was stirred at 90 C overnight. After cooling to room temperature, saturated NAHC03 was added, and the mixture was extracted with EtOAc. The organic extracts were collected and dried (NA2SO4). Evaporation of the solvent under reduced pressure and purification by column chromatography on silicagel (2% methanol in methylene chloride) afforded the desired 4-aminobenzene-1, 3-DICARBONITRILE as a white solid. GC/MS M/Z : 143 (M+, 100%), Rt 14.7 minutes

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; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 354814-19-0, 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. 354814-19-0 name is 5-Amino-2-(trifluoromethyl)benzonitrile, 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.

Method 6; To a solution of 5-amino-2-trifluoromethylbenzonitrile (380 mg, 2.04 mmol) in pyridine (5 mL) was added 2-trifluoromethylbenzenesulfonyl chloride (500 mg, 2.04 mmol) and DMAP (25 mg, 0.204 mmol). The reaction mixture was stirred at room temperature for 48 hours. The reaction was quenched by the addition of 2M HCI (aq) (50 mL) and the mixture extracted into EtOAc (50 mL). The organic layer was collected, washed with 2M HCI (aq) (50 mL) and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 10-60% (0.1 % ammonium hydroxide in MeCN) in water to afford the title compound as a colourless solid (318 mg, 40%). 1H NMR (400M Hz, CDCI3): delta ppm 7.19 (d, 1 H), 7.40 (d, 1 H), 7.56 (d, 1 H), 7.62 (d, 1 H), 7.64-7.78 (m, 2H), 7.91 (dd, 1 H), 8.20 (dd, 1 H). MS m/z 393 [M-H]-

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

Reference:
Patent; PFIZER LIMITED; OWEN, Robert McKenzie; STORER, Robert Ian; (82 pag.)WO2016/34971; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts