Month: September 2021

Related Products of 555-21-5,Some common heterocyclic compound, 555-21-5, name is 4-Nitrophenylacetonitrile, molecular formula is C8H6N2O2, 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.

Example-4 The following example illustrates the hydrogenation of various nitroaromatics as mentioned in Table 4. The hydrogenation of exemplary nitroaromatics was conducted under the following conditions. The procedure was similar to that for biphasic reactions [reaction numbers 7- 10, Table 2] Reaction conditions: Pressure: 400 psi; Temperature: 423K; Aqueous phase: 9×10-5 m3 ; Organic phase consists of neat substrate; catalyst FeS04. 7H20 : 7. 2×10-5 mol ; Fe: EDTANa2 1: 5; conversion in all cases was complete ; TOF calculated as mols of nitro compound converted per mol of Fe, § based on GC analysis. Table 4 Reaction No Substrate Substrate Yield of TOF (mols) corresponding hr~’ amine % 16 Nitrobenzelle 0. 090 98. 5 529 17 2-nitrotoluene 0. 0849 98. 75 457 18 2, 4-dinitrotoluene 0. 056 84. 63 134 19 4-nitrochlorobenzene 0.0635 96. 2 434 20 3-nitrochlorobenzene 0. 0635 99 400 21 2-nitrotoluene 0. 0849 98. 75 462 22 2-nitroanisole 0. 0820 89. 19 450 23 2-nitroaniline 0.0725 98. 2 116 24 4-nitrobenzoic acid 0.0598 85.8 393 25 4-nitro acetophenone 0.06 99 208 26 4-nitro benzylnitrile 0. 061 90 99

The synthetic route of 555-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; WO2005/70869; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 6136-68-1,Some common heterocyclic compound, 6136-68-1, name is 3-Acetylbenzonitrile, molecular formula is C9H7NO, 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.

Br2 (1 mmol) was dropwise added to a solution of 3-acetylbenzonitrile (1 mmol) in Et2O (15 ml) at 0 C., and then the mixture was stirred at r.t. for 4 h. Water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and was concentrated to give an oil, i.e., 3-(2-bromoacetyl)benzonitrile, which was directly used for the next step without purification.

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

Reference:
Patent; Hutchison Medipharma Enterprises Limited; US2009/118292; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 186517-05-5, name is 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, 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 186517-05-5, Computed Properties of C8H2F5N

Example 13 2,3-difluoro-6-trifluoromethylbenzaldehyde (Compound No. 44) STR30 2.0 g of 2,3-difluoro-6-trifluoromethylbenzonitrile was dissolved in 20 ml of anhydrous dichloromethane and the resultant solution was cooled down to -78 C. under a nitrogen atmosphere. To the solution was then gradually added dropwise with 7.1 ml of 1.5 M toluene solution of diisobutyl aluminium hydride (DIBAL) over 30 minutes. After stirring the solution at -78 C. for 1 hour, the solution was allowed to room temperature. The solution was then added with 7 ml of saturated aqueous solution of ammonium chloride, stirred for 30 minutes and subsequently added with 33 ml of 5% sulfuric acid. The mixture was then extracted with ether, and the organic layer obtained was washed with saturated saline solution and was then dried over anhydrous magnesium sulfate. After a process for the concentration, the organic solution was purified by using silica gel column chromatography to obtain 1.36 g of the title compound (nD 20.6-1.4357). The aldehyde compound obtained here was easily oxidized if it is left in the air and was converted to the corresponding benzoic acid (Compound No. 14).

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, 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 13726-21-1, 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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

KOtBu (370 g, 3.3 mol) was dissolved in THF (1.7 L) and stirred at -20 C. After 30 min, to the reaction mixture was added 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 1.32 mol) in THF (0.5 L) and then the resulting mixture was stirred for additional 30 min at the same temperature. CH3I (563 g, 3.96 mol) was added and the mixture was slowly warm to room temperature over 2 h with mechanical stirring. The reaction mixture was quenched with water in ice-bath and extracted with EtOAc (1.5 L x 2). The combined organic layers were washed with brine (3 L), dried over anhydrous MgS04, filtered and concentrated under reduced pressure to give 2-(4-chloro-3-methoxyphenyl)-2-methylpropanenitrile (14) as a amber liquid (269 g, 97%). 1H NMR (400MHz, CDC13): delta 7.35-7.37 (d, 1H), 7.05 (s, 1H), 6.95-6.97 (d, 1H), 3.94 (s, 3H), 1.72 (s, 6H).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Chloro-3-methoxyphenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WO2011/71565; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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