Month: August 2021

Synthetic Route of 6575-00-4, These common heterocyclic compound, 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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 solution of 40 (1.07 g, 5 mmol), 3,5-dichloro-benzonitrile (1.3 g, 7.56 mmol), K2CO3 (2.07 g, 15.0 mmol) and NMP (10 mL) was stirred and heated to 110° C. for 6 h. The reaction mixture was cooled to RT and diluted with H2O (50 mL) and twice extracted with EtOAc. The combined organic extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/hexane (10:90) to afford 0.328 g of 102a.

The synthetic route of 6575-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239881; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 261951-81-9, name is 3-Fluoro-2-(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 261951-81-9, HPLC of Formula: C8H3F4N

The compound obtained in Step 3 of Comparative Example 8 (148mg), 3- fluoro-2- (trifluoromethyl) benzonitrile (100 mg), sodium carbonate (164 mg) was added to DMSO (2 mL), 15 hours at 120. C. It was allowed to react. After filtration the insoluble matter to afford the title compound by HPLC column chromatography by preparative reverse phase (18mg, 17% yield).

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

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
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. 6621-59-6, name is 6-Bromohexanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 6621-59-6

In a solution of compound MI (2 g; 4,767 mmol) and N, N-diisopropylethylamine (8,10 ml; 47,67 mmol) in acetonitrile (80 ml) 6-bromohexanenitrile (6,32 ml ; 47,67 mmol) was added. Reaction mixture was stirred at 80C for 21 hours. After evaporation of the solvent, mixture was diluted with dichlormethane and water. The organic layer was dried over NA2SO4. The solvent was then evaporated under reduced pressure and the compound was purified on a silica gel column, eluent CH2Cl2 : MeOH: NH40H = 90: 9: 1.5. 532 mg of the compound 19 was obtained. MS (m/z) : 515,70 [MH] +. IR (CM~L)/KBR : 3444,2973, 2937,2875, 2247 (C_N), 1712, 1637,1459, 1375,1352, 1307,1265, 1179,1139, 1090,1052, 1004,958, 901,860, 810,773, 750,705, 670. The macrolide 19 (532 mg; 1.034 mmole) was dissolved in 25 mL of absolute ethanol and HYDROGENATED in a reactor with the catalyst PTOZ (53 mg) under pressure of 40 atm of H2 for 24 hours. The reaction mixture was filtered and the solvent was evaporated under reduced pressure. 463 mg of the mixture was obtained. The mixture was purified on a silica gel column, eluent CH2CI2 : MeOH: NH40H=6: 1: 0.1 ; 180 mg of amine 21 was obtained. MS (M/Z) : 519.74 [MH] +. Indomethacin D10 (62 mg; 0.174 mmole) was dissolved in 10 mL of dry dichloromethane. Triethylamine (0.189 mL), 47 mg of 1-hydroxybenzotriazole, the compound 21 (90 mg; 0.174 mmole) and 1- (3-DIMETHYLAMINOPROPYL)-3-ETHYL- carbodiimide hydrochloride (133 mg) were added. The reaction mixture was stirred in an inert atmosphere at room temperature for 24 h. The solvent was then evaporated under reduced pressure and the compound was purified on a silica gel column in the solvent system CH2Cl2 : MeOH: NH40H = 90: 8: 1.105 mg of compound 22 was obtained; MS (M/Z) : 858. 81 [MH] +.

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; PLIVA PHARMACEUTICAL INDUSTRY, INC.; WO2004/94449; (2004); 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. 4110-35-4, name is 3,5-Dinitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H3N3O4

General procedure: (Caution HMPA is not a friendly solvent). A solution of 0.5 g of a starting substrate in 15 ml of HMPA was kept at 155-160 C until the reactant was consumed (TLC; eluent, CHCl3). The reaction mass was cooled and poured into 150 ml of ice water. The precipitate was filtered off, washed with water and dried. The crude product was dissolved in chloroform, and the solution was filtered through a silica gel bed. The filtrate was evaporated, and the residue was crystallized from methanol.

The synthetic route of 4110-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dutov, Mikhail D.; Serushkina, Olga V.; Mendeleev Communications; vol. 23; 3; (2013); p. 174 – 175;,
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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H5FN2

To a mixture of 4-amino-3-fluorobenzonitrile 150 mg, triethylamine 0.38 mL, and THF 10 mL was added dropwise butyryl chloride 0.19 mL, and the resulting mixture was stilTed at room temperature for 1 hour. The reaction solution was filtered, and then concentrated under reduced pressure. To a mixture of the resulting residues and ethanol 10 mL was added dropwise a 50% aqueous hydroxylamine solution 0.22 mL, and the resulting mixture was stilTed at 80C for 2 hours. The reaction solution was concentrated under reduced pressure. To a mixture of the resulting residues and DMF 10 mL was added dropwise pyridine 0.22 mL at room temperature, and subsequently added dropwise trifluoroacetic anhydride 0.18 mL, and then the resulting mixture was stilTed at 100C for 2 hours. To the reaction solution was added water, and the precipitates were filtered, and the filtered substances were washed with water and hexane, and then dried under reduced pressure to give the Present compound 12 represented by the following formula 130 mg. 1HNMR (CDC13) oe: 8.59 (1H, t), 7.92-7.89 (1H, m), 7.86-7.82 (1H, m), 7.48 (1H, brs), 2.42 (2H, t), 1.83-1.74 (2H, m), 1.02 (3H, t)

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; YAMAMOTO, Masaoki; ARIMORI, Sadayuki; (34 pag.)WO2018/56340; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 118431-88-2, A common heterocyclic compound, 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, molecular formula is C6H7NO, 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.

The compounds listed below may be prepared in manner similar to the method described above. COMPOUND 638: 1-[2-chloro-4-(methylsulphonyl)phenyl]-2-cyano-3-cyclopropylpropan-1,3-dione, m.p. 145 C., starting from 3-cyclopropyl-3-oxopropanonitrile and 2-chloro-4-(methylsulphonyl)benzoyl chloride.

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; Rhone-Poulenc Agriculture Limited; US5804532; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 53312-81-5, 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of commercially available 5-amino-2-fluoro-benzonitrile (953 mg) in dry tetrahydrofurane (70 mL) were added benzyl chloroformate (1.20 mL) and potassium carbonate (1.16 g). The resulting suspension was stirred at room temperature for 16 h. Additional benzyl chloroformate (1.20 mL) and potassium carbonate (1.16 g) were added and stirring at room temperature was continued for 7 h. The mixture was diluted with ethyl acetate (70 mL), washed with water (2×70 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, cyclohexane/ethyl acetate) to afford the title compound (1.47 g; 78%). [MH]+=271.

The chemical industry reduces the impact on the environment during synthesis 5-Amino-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

10406-25-4, name is 4-(Aminomethyl)benzonitrile, 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. Application In Synthesis of 4-(Aminomethyl)benzonitrile

In a 200 ml four-neck flask equipped with an agitator, a thermometer, a gas conduit, and a reflux condenser, p-cyanobenzylamine (10.0 g) obtained in Preparation Example 3 was dissolved in ethyl acetate (90.0 g). While the reactor was cooled in a water bath, hydrogen chloride gas was fed into the vapor phase of the reactor while stirring. Immediately after the introduction of hydrogen chloride, heat generation was confirmed, and a white solid was precipitated. After the reaction mixture was cooled to room temperature, the white solid was separated through filtration and dried in a desiccator under vacuum, thereby yielding 12.6 g of p-cyanobenzylamine hydrochloride (yield based on p-cyanobenzylamine: 99%). Through high-performance liquid chromatographic analysis of the thus-obtained p-cyanobenzylamine hydrochloride, the p-cyanobenzylamine content in the hydrochloride was found to be 77 mass %. In addition, the hydrogen chloride content in p-cyanobenzylamine hydrochloride was found to be 23 mass % through anion chromatographic analysis. The thus-obtained p-cyanobenzylamine hydrochloride has a bulk density of 0.3 g/ml.

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Showa Denko K.K.; US6392083; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 6306-60-1, 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 6306-60-1 as follows.

A. 2-(2,4-Dichlorophenyl)-4,4,4-trifluoro-3-oxobutanenitrile Slurry 2,4-dichlorophenylacetonitrile (I) (5.0 g, 26.9 mmol, 186.04 g/mol) in ethyl trifluoroacetate (6.4 mL, 7.6 g, 142.08 g/mol) and add 20 mL anhydrous THF. Portionwise at ambient temperature add NaH (1.88 g, 47.1 mmol, 60% in mineral oil) over 5 minutes. Heat reaction to reflux (90 C. bath temperature) overnight. Evaporate to thick red-brown oil and partition between Et2O (100 mL) and H2O (60 mL). Separate layers and extract H2O with Et2O (2*75 mL). Acidify the aqueous layer with 1.0 N HCl to pH 1 (becomes cloudy white suspension) and extract aqueous layer with CH2Cl2 (3*100 mL). Dry pooled CH2Cl2 layers over Na2SO4, filter and concentrate to yellow oil (7.5 g, 26.5 mmol). Use without further purification. LCMS=281.9 (MH+); 279.8 (M-)

According to the analysis of related databases, 6306-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Neurogen Corporation; Pfizer Inc.; US6372743; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 1000339-52-5, name is 3-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. category: nitriles-buliding-blocks

Synthesis of 3-((3,4-dimethylphenyl)amino)-2-nitrobenzonitrile 3,4-Dimethylaniline (4.4 g, 36.1 mmol) was added into THF (60 mL). Sodium hydride (1.1 g, 45.2 mmol) was added and stirred for 1 hour. 3-Fluoro-2-nitrobenzonitrile (5 g, 30.1 mmol) was added and stirred for about 16 hours at room temperature. Water (2 mL) was added to quench the unreacted sodium hydride. The solvent was then evaporated and the residue was then purified by column chromatography using THF:hexane (1:4, v/v) as the eluent. 6.5 g (81% yield) of a red solid was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1000339-52-5, its application will become more common.

Reference:
Patent; Universal Display Corporation; KWONG, Raymond; LAM, Sze Kui; LAM, Siu Tung; TSANG, Kit Yee; LEE, Chi Hang; SZIGETHY, Geza; (159 pag.)US2016/218303; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts