Month: March 2021

Electric Literature of 13338-63-1, These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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.

Using the method of synthesizing an intermediate similar to that of Example 1,Take 0.01 mol of 3,4,5-trimethoxyphenylacetonitrile (5), 0.01 mol of 4-chlorobenzaldehyde and 20 mL of methanol into a 50 mL three-necked flask.Stirring to 60 C, adding 0.005 mol of sodium methoxide, constant temperature reaction 4-6 h,TLC scanning and detection, after the reaction is completed, it is cooled to room temperature, filtered, washed with water, dried, and recrystallized from methanol to obtain a pale yellow solid.Yield: 59.3%,

Statistics shows that 3,4,5-Trimethoxyphenylacetonitrile is playing an increasingly important role. we look forward to future research findings about 13338-63-1.

Reference:
Patent; Yanbian University; Bu Gonggaofamingren; (14 pag.)CN108503561; (2018); A;,
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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. 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H3FN2O2

A mixture of 3-fluoro-4-nitrobenzonitrile (2 g, 12 mmol), triethylamine (1.7 mL, 1.5 equivalents) and 4-fluoroaniline (1.7 mL, 1.5 equivalents) was heated at 60 C. under a nitrogen atmosphere for 60 hours. The resulting solid red-brown mass was cooled to ambient temperature and suspended in 50 mL of 1 N aqueous hydrochloric acid. The mixture was extracted extensively with dichloromethane and the organic extracts dried over anhydrous magnesium sulfate. Concentration of the organic extracts under reduced pressure afforded 2.9 g of a red solid, practically pure by LC/MS. MS (ESI) m/z 256 (M-H-)

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; Knopp Biosciences LLC; Resnick, Lynn; Topalov, George T.; Boyd, Steven A.; Belardi, Justin K.; Flentge, Charles A.; Hale, James S.; Harried, Scott S.; Mareska, David A.; Zhang, Kai; (112 pag.)US2016/75663; (2016); A1;,
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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. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, A new synthetic method of this compound is introduced below., name: 2,2-Dimethyl-2H-chromene-6-carbonitrile

To a stirred cooled solution of 2,2-dimethyl-6-cyano-2H-benzo[b]pyran (6.56 g) in dimethyl sulphoxide (65 ml) and water (1.30 ml) was added freshly crystallized N-bromosuccinimide (12.63 g) in one portion. Dilution with water after stirring for an additional 1 hour, and insolation via ethyl acetate gave trans-3-bromo-3,4-dihydro-2,2-dimethyl-6-cyano-2H-benzo[b]pyran-4-ol as a white crystalline solid (10.54 g), a small portion of which recrystallized from 60-80 petroleum ether had m.p. 128-128.5 C.

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; Beecham Group Limited; US4251537; (1981); A;,
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. 70591-86-5, name is 3-Bromobenzoylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6BrNO

Intermediate 2 (0092) 3-(3-bromophenyl)-lH-pyrazol-5-amine A mixture of 3-(3-bromophenyl)-3- oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-lH-pyrazol-5-amine (30 g, 126 mmol, 81 % yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37 – 7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H) = 240.1.

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 70591-86-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PEESE, Kevin; WANG, Zhongyu; LANGLEY, David, R.; KADOW, John, F.; NAIDU, Narasimhulu, B.; WO2015/123182; (2015); A1;,
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Reference of 1009-35-4, A common heterocyclic compound, 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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: Before each run, the system (see Fig.4) was allowed to equilibrate by pumping solvent through for 30min with the Tube-in-Tube device at 16bar of hydrogen. An omnifit cartridge (20.0mm OD, 15.0mm ID) containing 1g of Pd-C catalyst was used. To avoid an overpressure of the system in the event of blockage, the upper pressure cut-off limit on the Knauer pump was set to 25bar. With the injection loop disconnected from the flow line, the loop was opened and filled manually (using a syringe) with 3.6mL of a 0.076M solution of starting material in ethanol (excess starting material solution exiting the loop was recovered for reuse). The injection loop was then closed off and switched into the flow stream. The outlet from the system (downstream of the back-pressure regulator) was collected for 120min. The solvent was removed under reduced pressure (using a rotary evaporator followed by a 2-stage rotary vane pump) to afford the product.

The synthetic route of 1009-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dimitriou, Eleni; Jones, Richard H.; Pritchard, Robin G.; Miller, Gavin J.; O’Brien, Matthew; Tetrahedron; vol. 74; 47; (2018); p. 6795 – 6803;,
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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. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrN

General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mills, L. Reginald; Rousseaux, Sophie A.L.; Tetrahedron; vol. 75; 32; (2019); p. 4298 – 4306;,
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Reference of 67832-11-5, The chemical industry reduces the impact on the environment during synthesis 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Intermediate 24a) Methyl magnesium bromide (3 M in tetrahydrofuran) was added at rt drop wise to a solution of 4-bromo-2- methylbenzonitrile (4 g) in dry THF (15 mL) and was then heated to reflux for 2 h and then stirred at rt for 3 d. The mixture was chilled in an ice bath, saturated aqueous ammonium chloride solution (100 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and the remaining residue was treated with 4 N HCI at 0 C and was stirred at rt for 18 h. The mixture was extracted with EtOAc and the organic layer was washed with water, dried and the solvent was removed under reduced pressure to yield the desired product (88% 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, 4-Bromo-2-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastien; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108337; (2014); A1;,
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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. 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 177476-76-5

To a solution of 1 (3.46g, 10mmol) in 2-methoxyethanol (20mL) was charged 4-amino-3-methoxybenzonitrile or 4-amino-3-isopropoxybenzonitrile (11mmol) in 2-methoxyethanol (10mL), and the mixture was then heated to 100C, after which methanesulfonic acid (0.64mL, 0.96g, 11mmol) was added dropwise over 5min below 110C, and then the mixture was heated at 110C for 12h. The slurry was cooled to below 10C. The resulting solids were isolated by filtration and washed with cold 2-methoxyethanol until the filtrate was clear to obtain 2a or 2b. 4.1.1.1 4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-3-methoxybenzonitrile (2a) (0025) Yield: 63.2%; MS (ESI) m/z: 458.3 [M+H]+.

According to the analysis of related databases, 177476-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yu; Chen, Shaowei; Hu, Gang; Wang, Jiao; Gou, Wenfeng; Zuo, Daiying; Gu, Yucheng; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 123 – 136;,
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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. 22364-68-7, name is 2-(o-Tolyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H9N

Add dichloroethane (60g),Potassium hydroxide (0.15mol, 9.6g, content 90%),After stirring, the temperature was lowered to 15 C, and o-methylphenylacetonitrile (0.1 mol, 13.1 g) was added in one portion. Isoamyl nitrite (0.16mol, 18.7g) was added dropwise to the system, and after holding for 1 hour after the completion of the infiltration, 2-methyl-a-cyanobenzoxime potassium was obtained by suction filtration and dried. The yield was 96 %, The content is 93.5%.

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 22364-68-7.

Reference:
Patent; Jingbo Agrochemical Technology Co., Ltd.; Wang Shuaishuai; Cao Tongbo; Wang Xiangchuan; Li Hongxia; Cheng Guohua; Wang Jiangang; Ma Falu; Yu Lianyou; Wang Xue; (12 pag.)CN110396054; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, 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 939-79-7, Computed Properties of C8H6N2O2

A mixture of 3-nitro-p-tolunitrile (9.30 g, 57.4 mmol, 1 equiv) and 10% Pd/C (4.00 g, 3.76 mmol, 0.066 equiv) in ethanol (100 mL) was stirred under a hydrogen balloon at 23 0C for 20 h. The catalyst was filtered onto a pad a celite and washed with EtOAc (300 mL). The filtrate was concentrated to give 3- amino-4-methylbenzonitrile (1-2) as an off-white solid. 1H NMR (300 MHz, CDCl3) delta 7.10 (d, IH, J= 7.6 Hz), 6.98 (dd, IH, J = 7.9, 1.5 Hz), 6.89 (d, IH, J= 1.5 Hz), 3.78 (br s, 2H), 2.20 (s, 3H). LRMS m/z (M+H + CH3CN) 174.2 found, 174.1 required

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

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2007/88400; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts