Month: June 2021

Related Products of 134604-07-2,Some common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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 suspension of 2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropa ne-1-carboxamido)benzamide (C340) (600 mg, 1.326 mmol), 2-bromo-5-nitrobenzonitrile (361 mg, 1.591 mmol), cesium carbonate (605 mg, 1.856 mmol), tris(dibenzyideneacetone)dipaladium(0) ( Pd2(dba)s, 36.4 mg, 0.040 mmol), and bis(diphenylphosphino)-9,9-dimethylxa nthene (Xantphos, 69.0 mg, 0.119 mmol) in 1,4- dioxane (8.9 ml.) was evacuated under vacuum and backfilled with nitrogen three times. The reaction mixture was sealed under a blanket of nitrogen and heated to 60 C by microwave irradiation for 2 hours. The reaction mixture was diluted with ethyl acetate and filtered through Celite ” . The solvent was removed via rotary evaporation to give a deep red solid . The solid was suspended in dichloromethane ( 10 mL) and then collected by vacuum filtration, washing with more dichloromethane to afford the title compound as a red solid (0.598 g, 75% ) : N M R (400 MHz, Acetone- e) missing one amide NH in baseline delta 10.26 (s, 1H), 8.73 (d, J = 2.6 Hz, 1H), 8.62 (dd, J = 9.2, 2.6 Hz, 1 H), 8.55 (d, J = 9.2 Hz, 1H), 8. 13 (d, J = 2.6 Hz, 1H), 7.89 (dd, J = 8.8, 2.6 Hz, 1 H), 7.55 (d, J = 8.8 Hz, 1H), 7.51 (s, 3H), 3.67 (d, J = 8.3 Hz, 1H), 3.45 (d, J = 8.3 Hz, 1H); HRMS- ESI (m/z) [M + H]+ calcd for C24H 14G5N4O4, 596.9452 ; found, 596.9441 ; IR (thin film) 3341, 3074, 1673, 1568, 1545, 1509, 1473, 1413 cm 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Cyano-2-bromo-5-nitrobenzene, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
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Application of 7251-09-4, These common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, 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.

Take 148g of 4-cyano-2-methoxyaniline,Add 400g of di-tert-butoxycarbonyl dicarbonate and 5g of ZnOReaction at room temperature for 2h, after the reaction is over,The reaction system is filtered to remove ZnO,The residue was poured into 300 ml of water and extracted with 500 ml of ethyl acetate,The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was recovered under reduced pressure.246 g of white solid powder was obtained with a yield of 99%.

Statistics shows that 4-Amino-2-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 7251-09-4.

Reference:
Patent; Anhui Cheng Lian Pharmaceutical Technology Co., Ltd.; Liu Hui; Gong Bowen; Feng Chengliang; (11 pag.)CN110981800; (2020); A;,
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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 52516-37-7 as follows. Application In Synthesis of 2-(3,5-Dichlorophenyl)acetonitrile

(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (59): To a stirred mixture of 4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (9.8 g, 45 mmol) and (3,5-Dichloro-phenyl)-acetonitrile (8.0 g, 43 mmol) in anhydrous DMF (70 ml) at 0 C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (3.44 g, 86 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ethyl acetate and purified by silica gel column chromatography (eluent, EA:hexanes (1:9)) to afford 9.6 g (61%) of the title compound as a white solid. m.p. 135-136 C.; 1H NMR (200 MHz, CDCl3) delta 1.13(3H, d, J=7.0 Hz), 1.18 (3H, d, J=7.0 Hz), 2.97 (1H, m), 3.99 (6H, s), 5.33 (1H, s), 7.25-7.33 (3H, m).

According to the analysis of related databases, 52516-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guo, Hongyan; Kim, Choung U.; Kim, Hae Soo; Lee, Chong-Kyo; Lee, Ill Young; Mitchell, Michael L.; Son, Jong Chan; Xu, Lianhong; US2008/70920; (2008); A1;,
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Electric Literature of 887267-38-1, A common heterocyclic compound, 887267-38-1, name is 3-Chloro-2,4-difluorobenzonitrile, molecular formula is C7H2ClF2N, 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.

[0184] A dry flask was charged with sodium hydride (60% suspension in mineral oil, 3.8 g, 94 mmol) and 150 ml ofdry DMF, and cooled to 0 C followed by dropwise addition of di-tert-butyl malonate via syringe. After 30 min at 0 C, asolution of 3-chloro-2,4-difluorobenzonitrile in DMF (10ml) was added over a period of 15 minutes. The ice bath wasremoved and the reaction mixture was subjected to heating at 80 C in an oil bath for 12 hrs. The mixture was cooledto RT, quenched with saturated ammonium chloride, and partitioned between water and ethyl acetate. The organic layerwas concentrated and the resulting residue purified by flash chromatography (eluted with 2->10% hexanes / ethyl acetate)to provide di-tert-butyl (2-chloro-4-cyano-3-fluorophenyl)propanedioate. 1H-NMR (400 MHz, CDCl3) delta ppm 7.68 (m, 1H),7.53 (m, 1H), 5.06 (s, 1H), 1.52 (s, 18H). LC-MS (IE, m/z): 370 [M + 1]+.

The synthetic route of 887267-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
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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. 16532-79-9, name is 4-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., name: 4-Bromophenylacetonitrile

Reference Example 31b 2-(4-bromo-phenyl)-2-methyl-propionitrile. Using essentially the same procedure as in reference example 31a, except using (4-Bromo-phenyl)-acetonitrile. 1H NMR (CDCl3) d 1.70 (s, 6H), 7.34 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H). MS (EI) m/z 223, 225 Br pattern (M)+

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; Aventis Pharmaceuticals Inc.; US6541505; (2003); B1;,
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Synthetic Route of 35704-19-9, These common heterocyclic compound, 35704-19-9, name is N-(4-Cyanophenyl)acetamide, 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.

B. 3-nitro-4-acetamidobenzonitrile Sixty-seven grams of potassium nitrate were gradually stirred into 300 ml. of concentrated sulfuric acid at 9 C. to form a paste. Fifty grams of 4-acetamidobenzonitrile were added portionwise to the cold acid mixture. The reaction mixture was maintained at -5 C. for about 1 hour. The thick mixture was poured onto cracked ice. The product was collected and washed with cold water. The wet solid was added portionwise to about 400 ml. of warm acetic anhydride very carefully. Water was added to destroy the excess anhydride. The nitro product was collected and recrystallized from ethanol to yield 25.5 g. of 3-nitro-4-acetamidobenzonitrile m.p. 127-129 C. A second crop, 23 g., was obtained.

Statistics shows that N-(4-Cyanophenyl)acetamide is playing an increasingly important role. we look forward to future research findings about 35704-19-9.

Reference:
Patent; Eli Lilly and Company; US4018790; (1977); A;,
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Synthetic Route of 53312-81-5, 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 53312-81-5 as follows.

General procedure: To the solution of carboxylic acid (1 eq.) in DCM were added HATU (1.05 eq.), amine (1.1 eq.) and DIPEA (2 eq.). The mixture was stirred for 16 h at room temperature. Afterwards, the solution was washed with water and brine. The resulting organic layer was dried over MgSO4, and the solvent was removed by evaporation. The crude material was purified by flash chromatography (CH2Cl2:MeOH).

According to the analysis of related databases, 53312-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Egyed, Attila; Bajusz, David; Keser?, Gyoergy M.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1497 – 1508;,
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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. 13531-48-1, name is Methyl 3-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-cyanobenzoate

Into a 1000-mL round-bottom flask, was placed methyl 3-cyanobenzoate (20 g, 124.10 mmol, 1.00 equiv), methanol (200 mL), and 50% NH2OH (10 mL). The resulting solution was stirred for 1.5 h at 70 oC in an oil bath. The resulting mixture was concentrated under vacuum. This resulted in 24 g (100%) of methyl (Z)-3-(N’- hydroxycarbamimidoyl)benzoate as a tan solid.

According to the analysis of related databases, 13531-48-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, D.; PADILLA, Fernando; SKALITZKY, Donald, J.; TOOGOOD, Peter, L.; VANHUIS, Chad, A.; (172 pag.)WO2018/39539; (2018); A1;,
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60710-80-7, name is 3-Amino-4-methylbenzonitrile, 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. category: nitriles-buliding-blocks

DIPEA (1 mL; 5.8 mmol) was added to a solution of 3-amino-4-methylbenzonitrile(661 mg; 5 mmol) and 2,4-dichloro-1,3,5-triazine (750 mg; 5 mmol) in ACN (30 mL).The reaction mixture was stirred overnight at room temperature. The solvent wasremoved by evaporation and the residue was partionned between water and EtOAc. The organic layer was decanted, washed with water, then brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH; mobile phase: gradient from 0% EtOAc, 100% petroleum ether to 50% EtOAc, 50% petroleum ether). The fractions containing the product were collectedand evaporated to dryness yielding 700 mg (57%) of intermediate 543.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 51762-67-5, name is 3-Nitrophthalonitrile, 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 51762-67-5, category: nitriles-buliding-blocks

General procedure: 8-hydroxyquinoline-5-sulfonic acid (1.30 g, 5.78 mmol) was dissolved in dry DMF (8.00 mL) at 45 C and anhydrous K2CO3(1.5 g, 11.56 mmol) was added. After stirring for 15 min, 3-nitrophthalonitrile (1) was added dropwise in 2 h with efficient stirring. The reaction mixture was stirred under nitrogen at 45C for 4 days. After being cooled to room temperature, the mixture was poured into ca. 200 mL ice-water media and 1 M HCl (50 mL)was added in it. After completion of the precipitation approximately in 0.5 h, the creamy precipitate that formed was filtered and then washed with ca. 100 mL water until the washings became neutral. Column chromatography with methanol/dichloromethane (5:1) eluent on silica gel was employed to obtain the pure product. As expected, the yellow products were soluble in DMF and DMSO. Yield of 1: 1.36 g (67%); m.p.: Anal. Calc. for C17H9N3O4S (Mw:351.34): C, 58.12; H, 2.58; N, 11.96. Found: C, 57.90; H, 2.56; N,11.81%. FT-IR (KBr disc) n/cm-1: 3082, 3027, 2980 (Ar H), 2240 (CN), 1590, 1574, 1550 (Ar), 1273 (ArOAr), 1191, 1154 (SO2),789, 774, 674. 1H NMR (DMSO-d6): d ppm = 7.10-9.50 (m, 8H, ArH). UV/vis (DMSO): lambdamax = 299, 259.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Guensel, Arma?an; Bilgicli, Ahmet T.; Kirbac, Erkan; Gueney, Sevgi; Kandaz, Mehmet; Journal of Photochemistry and Photobiology A: Chemistry; vol. 310; (2015); p. 155 – 164;,
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