Month: July 2021

Application of 269411-71-4, The chemical industry reduces the impact on the environment during synthesis 269411-71-4, name is 3-Amino-5-methoxybenzonitrile, I believe this compound will play a more active role in future production and life.

The alcohol Ih (15 mg) was dissolved in dry DCE and 20 mg of sodium bicarbonate was added, followed by 2 ml of a phosgene solution in toluene (20%). The reaction mixture was stirred at room temperature for 3 h (full conversion to chloroimidate according to LC-MS) and then concentrated by rotary evaporation and dried from excess of phosgene in high vacuum (1.5 h). The dry reaction mixture was transferred into a “microwave” vial (2-5 ml), mixed with dry DCE (3 ml), 3-amino-5-methoxy- benzonitrile (2 eq), potassium carbonate (9 mg, 1.5 eq), pulverized molecular sieves (4A, 5 mg) and heated in a microwave at 100 0C for 45 min. The reaction mixture was passed through short pad of silica (eluent DCM, then 10% methanol in DCM). The resulting fractions containing the desired carbamate compound were combined, concentrated by rotary evaporation and purified by column chromatography on YMC silica (15 g, ethyl acetate/petroleum ether 1 :3 to remove excess of aniline, followed by dichloromethane and then 2% methanol in dichloromethane) to give the title compound as a powder (15 mg, 8%), [M+H]+ 628.

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-Amino-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96001; (2008); 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. 3032-92-6, name is 4-Ethynylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H5N

Sequentially adding a catalyst in the reaction bottle (14.0 mg, 0.025 millimole, 5mol %), cesium carbonate (32.6 mg, 1.0 mmol), 4-ethynyl phenyl nitrile (63.6 mg, 0.5 mmol),N,N-dimethylformamide(3 ml), into the carbon dioxide, in the 50 C, reaction under normal pressure 16 hours. Reaction cooling to room temperature, diluted with water, acidified with hydrochloric acid, diethyl ether extraction, washing with saturated sodium chloride for ether level, dry anhydrous sodium sulfate, obtained product is vacuum to remove the solvent, the yield is 93%

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 3032-92-6.

Reference:
Patent; Suzhou University; Sun, Hongmei; Zhu, Fan; Lu, Bing; (10 pag.)CN105585473; (2016); A;,
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. 16532-79-9, name is 4-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrN

P-Bromophenylacetonitrile (5 g, 25.505 mmol) and iodine (6.5734 g, 25.505 mmol) were placed in a 250 mL reaction flask and the mixture was purged with argon three times until the bottle had no oxygen and water.A solution of sodium methoxide (2.8933 g, 5.356 mmol) in anhydrous methanol (8.680 g, 14.613 ml) was added dropwise to the above solution at -78 C under oxygen and water, and the whole drop was maintained Argon atmosphere.After the dropwise addition, the temperature was gradually raised to 0 C, and the reaction was continued for 3 hours.After the reaction, the reaction was quenched with a 5% dilute hydrochloric acid solution, and the reaction was stirred for 12 hours.After the reaction was complete, the solution was filtered and the filter cake was washed twice with methanol and water.The resulting solid was dried in a vacuum oven.The final product was white powder compound 1 (3.1143 g, 63% yield).

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; Jilin University; Xu Bin; Tian Wenjing; Yan Lulin; Ji Guang; (14 pag.)CN106084873; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 213598-11-9, 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. 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3-cyano-4-(propan-2-yloxy) benzoic acid: To a solution of methyl 3-cyano-4- (propan-2-yloxy)benzoate (5 g, 22.81 mmol, 1.00 equiv) in methanol/ water ( 30: 10 mL) was added sodium hydroxide (1.77 g, 2.30 equiv). The resulting solution was stirred for 2 h at 25 C. The pH value of the solution was adjusted to 3 with hydrogen chloride (1 Mol/L). The resulting solution was extracted with ethyl acetate (3 x 20 mL), and the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under vacuum to afford 4.4 g of 3-cyano-4-(propan-2-yloxy) benzoic acid as a white solid.

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, Methyl 3-cyano-4-isopropoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); 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. 5332-06-9, name is 4-Bromobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromobutanenitrile

(R)-4-((2-(1′-(3-chlorobenzyl)-1-(2-fluoro-6-(trifluoromethyl)benzyl)-2,4-dioxo-1H-spiro[furo[3,4]pyrimidine-5,4′-piperidin]-3(2H.4H,7H)-yl)-1-phenylethyl)amino)butanenitrile (1 -16) (10 g, 15 mmol) was dissolved in acetonitrile (200 mL), and then Nal (6.2 g, 45 mmol), K2C03 (6.8 g, 45 mmol) and 4-bromobutanenitrile (2.3 mL, 22.5 mmol) were added to the mixture in sequence, followed by stirring for 12 hrs at 95 C. The resulting solution was cooled down to room temperature, filtered, and concentrated under reduced pressure to remove acetonitrile therefrom. The resulting solution was diluted with dichloromethane, washed with a saturated aqueous ammonium chloride solution, and the organic layer was separated. The organic layer was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (eluent: dichloromethane/methanol = 98/2-95/5) and dried under vacuum to obtain the title compound as white foam (8.2 g, yield: 75%).

According to the analysis of related databases, 5332-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS CO., LTD.; KIM, Seon-Mi; KIM, Jae-Sun; LEE, Minhee; LEE, So-Young; LEE, Bong-Yong; SHIN, Young Ah; PARK, Euisun; LEE, Jung A; HAN, Min-Young; AHN, Jaeseung; YOO, Taekyung; KIM, Hun-Taek; WO2013/129879; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 85363-04-8, These common heterocyclic compound, 85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, 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.

Intermediate 641 ,1 -Dimethylethyl [2-(hydroxyamino)-2-iminoethyl]carbamateA flask was charged with 1 ,1 -dimethylethyl (cyanomethyl)carbamate (1 .562 g, 10 mmol) then filled with ethanol (15 mL) and hydroxylamine (50% w/w in water, 2.451 mL, 40.0 mmol) and the resulting mixture was stirred at 80C for 1 .5 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in DCM and the organic phase was dried using a phase separator then concentrated in vacuo. Trituration of the residue in Et20 gave 1 ,1 -dimethylethyl [2-(hydroxyamino)-2-iminoethyl]carbamate (1 .8 g, 9.51 mmol, 95 % yield) as a white solid which was used in the next step without further purification.

The synthetic route of 85363-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 3759-28-2, These common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, 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.

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

Statistics shows that 2-(Cyanomethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 3759-28-2.

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, molecular formula is C8H3ClF3N, 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. Recommanded Product: 2-Chloro-5-trifluoromethylbenzonitrile

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha -trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C. for 21/2hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha -trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 328-87-0, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US4046798; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, 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 133541-45-4, Recommanded Product: 4-Bromo-2,5-difluorobenzonitrile

EXAMPLE 28 4-Bromo-2-{[(1R)-3-(cyclopropylamino)-1-(phenyl)propyl]oxy}-5-fluorobenzonitrile oxalate Prepared by the method of Example 25 using (R)-alpha-(2-chloroethyl)benzenemethanol and 4-bromo-2,5-difluorobenzonitrile initially before converting into the title compound via in situ conversion to the iodo compound and treatment with cyclopropylamine. The free base was treated with a 50% saturated solution of oxalic acid in ether. The resultant white solid was collected via filtration to yield the title compound (41 mg, 4.2%). MS APCI+ve m/z 390 [(M+H)+]. 1H NMR 400 MHz (d6-DMSO) delta7.96 (d, 1H), 7.49 (d, 1H), 7.45-7.39 (m, 3H), 7.39-7.31 (m, 2H), 5.82-5.74 (m, 1H), 3.16-3.00 (m, 2H), 2.74-2.64 (m, 1H), 2.38-2.25 (m, 1H), 2.24-2.11 (m, 1H), 0.79-0.64 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (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. 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

EXAMPLE 15 3-Fluoro-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.00 g, 3.86 mmol) in 200 mL of isopropanol was added 3-fluoro-p-anisidine (0.60 g, 4.25 mmol). This mixture was heated to reflux to give a clear yellow solution. To this solution, triethylorthoformate (1.72 mL, 10.34 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. An additional 2 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. An additional 2 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the white solid was collected by filtration, washed with isopropanol, and dried overnight at ~40 C. under reduced pressure. Purification by suspension in hot ethyl acetate followed by addition of cold hexanes gave 1.08 g (68%) of 3-fluoro-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide as a white solid, mp 275-276 C.; MS 408.1, 410.1 (M-H)- Analysis for C18H14Cl2FN3O3; Calcd: C, 52.70; H, 3.44; N, 10.24. Found: C, 52.44; H, 3.26; N, 10.14.

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 846023-24-3.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts