Author: Jessica.F

Some common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, molecular formula is C9H6ClNO, 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. Computed Properties of C9H6ClNO

EXAMPLE 41 Preparation OF 3- [5-AMINO-4- (3-CHLOROBENZOYL)-PYRAZOL-1-YL]-N-CYCLOPROPYL-4- methyl-benzamide A. 2- (3-Chlorobenzoyl)-3-phenylaminoacrylonitrile A solution of 3-chlorobenzoylacetonitrile (476 mg, 2.66 mmol, 1.0 eq) and diphenylformamidine (522 mg, 2.66 mmol, 1.0 eq) in 25 mL of toluene was stirred at room temperature for 2h then heated to 100 C overnight. The solution was cooled and diluted with hexanes. The resulting solid was filtered and dried to provide the desired product (566 mg, 75%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21667-62-9, its application will become more common.

Reference:
Patent; TRIAD THERAPEUCTICS, INC.; WO2005/9973; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 654-70-6, 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. 654-70-6 name is 4-Cyano-3-trifluoromethylaniline, 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.

1) Preparation of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethyl-benzonitrile (1.1); Compound 1.1 can be prepared by method ?N-A?. To this end, 14.74 g (79.21 mmol) of 4-amino-2-trifluoromethylbenzonitrile were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with stirring with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture which was then stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium hydrogencarbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified chromatographically using silica gel with 2:1 heptane/ethyl acetate. This afforded 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.1 with melting point 208-211 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Cyano-3-trifluoromethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2011/46105; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 50397-74-5, These common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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 another example of a dye compound according to Formula 1, the dye compound has the following formula: This compound is (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide may be synthesised as follows: A suspension of 4-Amino-3-bromobenzonitrile (15.0 g, 76.1 mmol) in a mixture of AcOH (120 mL) and EtCO2H (80 mL) was warmed until a clear solution was obtained and then cooled to 8 C. with an ice bath. 40% nitrosyl sulfuric acid (14.3 mL, 83.7 mmol) was added drop wise. The mixture was stirred 1 h at 7 C. and then added slowly to a solution of N-{3-[bis(2-ethylhexyl)amino]-4-ethoxyphenyl}-2-ethylhexanamide (35.0 g, 69.6 mmol) in 1,4-dioxane (120 mL) and acetic acid (30 mL) cooled in an ice bath. The mixture was stirred at 7 C. during 1 h and then hydrolyzed by drop wise addition of 33% NaOH (75 mL) while cooling in an ice bath. After 30 minutes, the mixture was poured into water and extracted with toluene. The combined organic layers were washed with water and the solvent evaporated. Purification by column chromatography (silicagel, heptane/EtOAc 60/1) afforded (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2-bromo-4-cyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (35 g). This was dissolved in dimethylformamide DMF (400 mL) and copper(I) cyanide (17.6 g, 196.9 mmol) was added while the mixture was cooled in a water bath. After 20 h of stirring at RT, the reaction mixture was poured into 15% ammonia and extracted with toluene (3*). The combined organic layers were washed with ammonia, water and dried with Na2SO4. After evaporation of the solvent the residue was purified by column chromatography (silicagel, heptane/EtOAc 80/1 to 30/1) to obtain (E)-N-(5-(bis(2-ethylhexyl)amino)-2-((2,4-dicyanophenyl)diazenyl)-4-ethoxyphenyl)-2-ethylhexanamide (19.8 g, 39% yield) as a purple oil.

Statistics shows that 4-Amino-3-bromobenzonitrile is playing an increasingly important role. we look forward to future research findings about 50397-74-5.

Reference:
Patent; Amazon Technologies, Inc.; Leguijt, Robin; Mans, Jurrinn; Sandhu, Sukhdip; US2015/370062; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 85068-32-2, 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. 85068-32-2 name is 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, 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.

In a round bottom flask 1,3,5-Benzenetricarbaldehyde 1 (0.5 g,3.1 mmol) and trifluoromethyl substituted phenylacetonitrile 2(9.7 mmol) were taken in absolute ethanol (300 mL). Sodium ethoxide(0.80 g, 11.6 mmol) was added drop wise to the above solution.Under protection from air, the solution was heated to reflux for 3 h. Then, volatiles were removed under reduced pressure. Under protection from air, 200 ml of water was added to the residue. The mixture was repeatedly extracted with small portions (30 mL) of dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum condition to leave the residue. The resulting residue was chromatographed on silica gel (Wako C-300) using dichloromethane/hexane (1:1) mixed solvent as an eluent to give the desired compound(1.9 g, 90% for 3a, 2.4 g, 88% for 3b) as pale yellow solids.Compound 3a, pale yellow solid, M.p. 231-232 C; 1H NMR(400 MHz, CDCl3) 7.72 (s, 3H, aryl H), 7.76 (d, 6H, aryl H, J = 7.3 Hz),7.86 (d, 6H, aryl H, J = 7.3 Hz), 8.48 (s, 3H, ethenyl H). EI-MS (75eV):m/z 663 (M+). Elemental analysis calculated for C36H18F9N3: C,65.16%; H, 2.73%; N, 6.33%. Found: C, 65.30%; H, 2.55%; N, 6.49%.Compound 3b, pale yellow solid, M.p. 249-251 C; 1H NMR(400 MHz, CDCl3) 7.79 (s, 3H, aryl H), 7.99 (s, 3H, aryl H), 8.16 (s, 6H,aryl H), 8.51 (s, 3H, ethenyl H).EI-MS (75eV): m/z 867 (M+).Elemental analysis calculated for C39H15F18N3: C, 53.99%; H, 1.74%;N, 4.84%. Found: C, 53.81%; H,1.85%; N, 4.64%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Moriguchi, Tetsuji; Yakeya, Daisuke; Jalli, Venkataprasad; Journal of Molecular Structure; vol. 1185; (2019); p. 403 – 409;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 68119-31-3 as follows. HPLC of Formula: C9H5F2NO2

A mixture of (2,2-difluoro-l,3-benzodioxol-5-yl)-acetonitrile (1.0 eq), 50 wt % aqueous KOH (5.0 eq) l-bromo-2-chloroethane (1.5 eq), and OCt4NBr (0.02 eq) is heated at 70 0C for 1 h. The reaction mixture is cooled then worked up with MTBE and water. The organic phase is washed with water and brine then the solvent is removed to afford (2,2-difluoro-l,3-benzodioxol-5-yl)-cyclopropanecarbonitrile.

According to the analysis of related databases, 68119-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; YOUNG, Christopher; WO2010/37066; (2010); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 69395-13-7, 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. 69395-13-7 name is 4-(2-Hydroxyethyl)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.

Intermediate 33: N’-hvdroxy-4-(2-hvdroxyethyl)benzenecarboximidamide; Hydroxylamine (5 mL) was added to a solution of 4-(2-hydroxyethyl)benzonitrile (2.43 g; 16.5 mmol) in ethanol (30 mL) and the mixture was heated to 80 C in a sealed tube for 3 hours. The solvent was removed in vacuo and the residue triturated with water to yield Intermediate 33 (2.95 g; 99 %) as a white solid which was used without further purification.20 1H NMR (DMSO-d6, 400MHz) delta 9.58 (1 H, s), 7.60 (2 H, d, J = 7.9 Hz), 7.24 (2 H, d, J = 7.9 Hz), 5.75 (2 H, s), 4.75-4.69 (1 H, m), 3.64 (2 H, d, J = 6.6 Hz), 2.80-2.72 (2 H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Hydroxyethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 79630-23-2, 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. 79630-23-2, name is 3-Bromo-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-bromo-4-fluorobenzonitrile (1.0 equivalent), 2- (trifluoromethoxy) benzeneboronic acid (1.25 equivalent), palladium acetate (0.005 equivalent) and triphenylphosphine (0.01 equivalent) were sequentially charged to a multi-necked flask. After purging the flask with nitrogen, toluene (5ML/GRAM. of 3-bromo-4-fluorobenzonitrile) was added and the resulting slurry was stirred while bubbling nitrogen subsurface for about 20 minutes. In a separate flask, an aqueous potassium phosphate solution was prepared by dissolving solid potassium phosphate (2.0 equivalents) into water (2ML/GRAM of potassium phosphate). The resulting solution was de-oxygenated by bubbling nitrogen subsurface while stirring for about 30 minutes. The aqueous potassium phosphate solution was added to the toluene slurry and the reaction mixture was warmed to 60-65 C by heating with steam. The progress of the reaction was monitored by HPLC and the reaction temperature was held between 63-69 C. When 3-bromo-4- fluorobenzonitrile was consumed, heating was discontinued and the reaction mixture was cooled to RT using an ice bath. The aqueous layer was siphoned from the vessel and Ecosorb C-941 (0.5 GRAM/GRAMS of 3-bromo-4-fluorobenzonitrile, commercially available from Graver Technologies, Glasgow, Delaware) was added to the reaction vessel. The resulting black slurry was stirred at RT for 15 hours. The carbon was removed by filtering the slurry through a pad of solka flok on a filter pot. The filter cake was washed with toluene (4ML/GRAM of 3-bromo-4-fluorobenzonitrile). The combined filtrates were batch concentrated (40-50 C) to provide the biaryl nitrile product as a thick, light-orange oil (94.0% yield).

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-Bromo-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2004/83189; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. SDS of cas: 57381-49-4

To a solution of 2-bromo-4-chlorobenzonitrile (500 mg, 2.3 mmol), in dry THF (50 mL) was added slowly borane-THF complex (1 M, 12 mL, 1 1 .5 mmol) at 0 C before refluxing for 1 h. After cooling down, 1 M HCI in MeOH (20 mL) was charged slowly with ice cooling. The solvent was removed by concentration in vacuo before water (0.61 mmol/mL to benzonitrile) was charged, then washed by Et20 (0.61 mmol/mL to benzonitrile) before basifying with 2 M NaOH solution to pH 12. Et20 (15 mL) was added and the mixture was washed with water (3 x 15 mL) and brine (1 mL). The organic phase was dried (MgS04) and concentrated in vacuo to give a yellow oil (345 mg, 68%). LCMS (EST) m/z = 220.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-49-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1558-81-2, Adding some certain compound to certain chemical reactions, such as: 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, 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 1558-81-2.

A solution of 1-cyano-cyclopropanecarboxylic acid ethyl ester (1.0 g, 7.18 mmol), concentrated hydrochloric acid (1.5 mL), and platinum oxide (0.20 g) in methanol (50 mL) was pressurized with 50 psi of hydrogen for 2 hr. The heterogeneous mixture was filtered through Celite and concentrated to give the desired amine as a hydrochloride salt (1.26 g, 97%). MS found: (M+H)+=144

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 1558-81-2.

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 71682-97-8, These common heterocyclic compound, 71682-97-8, name is 3-(3,4-Difluorophenyl)-3-oxopropanenitrile, 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.

[0531] A thoroughly mixed mixture of 3-ethyl 4-methyl 2-hydrazinylthiophene-3 ,4- dicarboxylate (0.3 g, 1.228 mmol, 1 eq) and 3-(3,4-difluorophenyl)-3-oxopropanenitrile (0.222 g, 1.228 mmol, 1 eq) in an open vial was stirred neat at 130 °C for 1.5 h. The melted liquid becomes thick solid which is triturated in DCM/MeOH. The crude product was purified on flash system using a 24 g silica column eluting with 1-10 percent methanol in DCM over 12 column volumes. The pure fraction was pooled and concentrated to get 0.49 g (Yield = 84 percent) of white solid.

The synthetic route of 71682-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts