Month: November 2020

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. 10406-25-4 name is 4-(Aminomethyl)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. 10406-25-4

General procedure: Under nitrogen atmosphere, a Schlenk tube was sequentially charged with cyclicdiaryliodonium salt (1.0 equiv), copper catalyst A1 or A2 (5.0 mol%), Na2CO3 (3.0 equiv) anddichloromethane (0.05 M). After the mixture was chilled to proper temperature, the appropriateamine (1.2 equiv) was added and stirred for the time indicated in the experimental procedures.The reaction mixture was filtered through a plug of celite with ethyl acetate. The filtrate wasconcentrated under reduced pressure, and the residue was purified by column chromatographyon silica gel to deliver the corresponding product.

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

Reference:
Article; Zhao, Kun; Duan, Longhui; Xu, Shibo; Jiang, Julong; Fu, Yao; Gu, Zhenhua; Chem; vol. 4; 3; (2018); p. 599 – 612;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2941-23-3, 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. 2941-23-3, name is 2-Aminocyclopent-1-enecarbonitrile, A new synthetic method of this compound is introduced below.

Example 2; Hydrogenation of CPI to AMC Using a Palladium-Promoted Raney 2000 Nickel; [0019] The same pre-treatment of catalyst was done as in Example 1, with the exception that the catalyst was 0.5 wt. percent palladium-promoted Raney Ni 2000. One gram of catalyst plus 10 grams of starting CPI was heated and stirred 6 hr at 150¡ã C. with 1500 psi H2 (with re-pressure) and excess NH3. Gas chromatography showed 100percent conversion and >95percent selectivity to AMC.

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; Amey, Ronald L.; Mattson JR., Ronald H.; US2004/249214; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

170572-49-3, Adding a certain compound to certain chemical reactions, such as: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, 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 170572-49-3.

Method B. Sodium bromate Bromination To a suitable reactor was added dichloromethane (40 L) and 3-fluoro-4-methylbenzonitrile (4 kg, 18.7 mol) followed by a solution of sodium bromate in water (13.45 kg, 89.1 mol dissolved in 53.6 L water). The reaction mixture was cooled to 0-5 C. A solution of sodium bisulfite (9.25 kg dissolved in 42 L water) was added over a period of 2-3 hours while maintaining a batch temperature of 10-20 C. (the reaction is exothermic). After the addition was complete, a 200 W lamp was shined on the reactor and the batch temperature was increased to 25-30 C. The light and temperature were continued until product was 70-75% by HPLC. The light was removed, stirring was stopped and the reaction was permitted to settle for 15 minutes. The organic layer was removed and the remaining aqueous layer was extracted with dichloromethane twice. The organic layers were combined and washed four times with 10% sodium thiosulfate solution. The organic layer was then washed with brine (10 L) and dried with sodium sulfate. The organic layer was concentrated and then petroleum ether was added and distilled to dryness twice to remove all dichloromethane. Petroleum ether (3 L) was added and the slurry was cooled to 5-10 C. for 1 hour. The slurry was filtered and washed with cold petroleum ether. The product was dried in a vacuum oven at 40-45 C. to give the title compound (3.2 kg, 50.4% yield) as an off-white solid. Representative procedure for recovery of the title compound from mother liquor: The crude mass (~36% 4-(bromomethyl)-3-fluorobenzonitrile and 59% gem-dibromide) obtained from concentration of mother liquor (300 g) and 2 equivalents of diisopropyl ethyl amine (based on gem-dibromide) was dissolved in acetonitrile (3 L) and water (50 mL). The reaction was cooled to 0-5 C. and diethyl phosphite (169 g, 1.22 mol) was added over 30 minutes (addition was exothermic). The reaction was stirred for 60-90 min at 0-5 C. and was monitored by TLC. When dibromide was no longer present by TLC, water (3.3 L) was added and the resulting slurry was filtered. The filter cake was washed with water and dried in a vacuum oven (until the moisture content was <1%) to give 202 g (98 AP by HPLC) of additional title compound. According to the analysis of related databases, 170572-49-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; Bristol-Myers Squibb Company; US2009/111858; (2009); 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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, A new synthetic method of this compound is introduced below., 6011-14-9

To a solution of aminoacetonitrile hydrochloride (25.27 g) and K2C03 (109.80 g) in THF/H20 (200 mL/400 mL) at 5-10C was added benzyl chloroformate (45.22 g) under an atmosphere of nitrogen. The mixture was stirred at room temperature for 15 h and then quenched with NH4C1(aq) (100 mL, 2 M). The resulting mixture was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to get the crude product S-VI-II (46.88 g, y: 90%).

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; NATIONAL HEALTH RESEARCH INSTITUTES; SHIH, Chuan; SHIA, Kak-Shan; WU, Chien-Huang; CHOI, Ming-Chen; SONG, Jen-Shin; WANG, Yun; (84 pag.)WO2018/132326; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

610-66-2, A common heterocyclic compound, 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.

Absolute ethanol (2,250 ml) and 1,500 g (9.25 moles) of o-nitrophenylacetonitrile are charged into a 22 liter flask. The suspension is cooled to 5-10 and hydrogen chloride is bubbled into the mixture for 2.5 hours. The reaction mixture is stirred at 10 under nitrogen atmosphere overnight. It was then diluted with 16,000 ml of ether and stirred for 1 hour; the solid is collected by filtration, washed with 4*1,000 ml of ether and dried (5 mm Hg/40) to give ethyl 2-(2-nitrophenyl)acetimidate hydrochloride, m.p. 122-123 (dec).

The synthetic route of 610-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4460587; (1984); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The chemical industry reduces the impact on the environment during synthesis 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, I believe this compound will play a more active role in future production and life. 60702-69-4

Example 34A(2Z)-3-Amino-3-(2-chloro-4-fluorophenyl)prop-2-enonitrile; Under argon, 35.3 g (273 mmol) of diisopropylamine were initially charged in 450 ml of THF at -70 C. in a three-necked flask with mechanical stirrer. 145 ml of N-butyllithium solution (1.6 M in hexane, 237 mmol) were added dropwise at such a rate that the temperature did not exceed -60 C. The mixture was stirred for 30 min, and a solution of 12.7 ml (241 mmol) of acetonitrile in 100 ml of THF was then slowly added dropwise and the suspension was stirred for 30 min. A solution of 25 g (160.7 mmol) of 2-chloro-4-fluorobenzonitrile in 100 ml of THF was added dropwise, and the mixture was stirred at -70 C. for 20 min. The mixture was allowed to slowly warm to RT and stirred at RT for a further 16 h. 150 ml of water were added, most of the THF was distilled off and water and dichloromethane were added. The organic phase was washed with saturated aqueous sodium chloride solution. Removal of the solvent gave an oil. A solid could be obtained by trituration with diisopropylether and subsequent filtration with suction. Drying under high vacuum gave 12.58 g (36% of theory) of the product. This was a mixture of E and Z isomers which was used without further purification.LCMS (Method 8): Rt (isomer 1)=0.83 min. (m/z=197 (M+H)+); Rt (isomer 2)=1.02 min. (m/z=197 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=7.52 (dd, 1H), 7.44 (dd, 1H), 7.26 (m, 1H), 6.99 (s, br, 2H), 3.77 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 60702-69-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLESCHAFT; US2011/144131; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

143879-80-5, The chemical industry reduces the impact on the environment during synthesis 143879-80-5, name is 2,3,4-Trifluorobenzonitrile, I believe this compound will play a more active role in future production and life.

4- 4-CYANO-2, 3-DIFLUORO-PHENYL)-PIPERAZINE-L-CARBOXYLIC ACID TERT-BUTYL ester To a solution OF N-BOC-PIPERAZINE (0.65 g) in DMA (20 mL) was slowly added a solution of 2, 3, 4-trifluorobenzonitrile (0.49 g) in DMA (10 mL). The reaction mixture was stirred for 2 hours at 80C. After such time the solvent was removed in vacuo and purified by column chromatography (SIO2) to yield the title compound as white solid (0.76 g).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/23260; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

63069-50-1, 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 63069-50-1 as follows.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

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; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
Nitrile – Wikipedia,
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15760-35-7, The chemical industry reduces the impact on the environment during synthesis 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, I believe this compound will play a more active role in future production and life.

Sodium periodate (43.0 mmol, 9.20 g) was added portion-wise to a solution of 3- methylenecyclobutanecarbonitrile (21.5 mmol, 2.00 g) and ruthenium trichloride (0.47 mmol, 98 mg) in (0880) dichloromethane : acetonitrile : water (1:1:1.5; 175 mL) . The resulting suspension was vigorously stirred (0881) overnight. The organic phase was separated then the aqueous phase was further extracted with dichloromethane (3 x 50 mL) . The combined organic extracts were dried (MgSOi) then passed through a silica plug. The solvents were removed under reduced pressure to give the title compound as a dark solid (1.58 g, 74%).

The chemical industry reduces the impact on the environment during synthesis 3-Methylenecyclobutanecarbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

21524-39-0, Adding a certain compound to certain chemical reactions, such as: 21524-39-0, name is 2,3-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 21524-39-0.

General procedure: The respective 2-hydroxybenzenesulfonamide 5 (2 mmol) and 1,2-dihaloarene (1-halo-2-nitroarene) partner 9 (2 mmol) were combined in anhydrous DMF (7 mL) with freshly calcinated K2CO3 (829 mg, 6 mmol) and the mixture was kept, with stirring, at the temperature and for the time period indicated in Table 2. DMF was removed in vacuo and the residue was treated with water (10 mL), which caused a viscous oil to separate. It was extracted with CH2Cl2 (5 mL), the organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using an appropriate gradient of CH2Cl2 in hexanes as eluent.

According to the analysis of related databases, 21524-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sapegin, Alexander; Panova, Valeria; Reutskaya, Elena; Smirnov, Alexey V.; Krasavin, Mikhail; Tetrahedron; vol. 72; 47; (2016); p. 7570 – 7578;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts