Month: November 2020

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 40497-11-8 as follows. 40497-11-8

In a 250 mL round-bottomed three-necked flask, 0.01 mol of 3-methylaniline and a small amount of ethanol were added,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly dropping into the flask,After the reaction was completed 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction 2 h.Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,Partial distillation of the solvent under reduced pressure gave 1.50 g of product,Yield 76.2%

According to the analysis of related databases, 40497-11-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
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127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-azanylcyclopropane-1-carbonitrile hydrochloride (671.53 mg, 5.66 mmol), (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-pyridyl)propanoic acid (2 g, 5.15 mmol) and HATU (2.15 g, 5.66 mmol) were suspended in DMF (15 mL). DIPEA (2.63 mL, 15.45 mmol) was added and mixture stirred for 16H at room temperature. The mixture was diluted with EtOAc and washed with water and brine. Organic layer was separated, dried (Na2SO4), filtered and concentrated to get a crude which was purified by column chromatography. Biotage SNAP KP-SiO2 100 g; eluent: solvent A: petroleum ether; solvent B: EtOAc.

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

Reference:
Article; Nizi, Emanuela; Sferrazza, Alessio; Fabbrini, Danilo; Nardi, Valentina; Andreini, Matteo; Graziani, Rita; Gennari, Nadia; Bresciani, Alberto; Paonessa, Giacomo; Harper, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1540 – 1544;,
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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. 403-54-3 name is 3-Fluorobenzonitrile, 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. 403-54-3

(a) 3-Cyano-4-nitrofluorobenzene m-Fluorobenzonitrile (96.8 g., 0.8 mol) is added in two and one-half hours to a mixture of concentrated sulfuric acid (600 ml.) and potassium nitrate (80.9 g., 0.8 mole) at 3-6 C., then allowed to warm to 25 C. The mixture is poured over cracked ice (3000 ml.), extracted with chloroform (5*250 ml.), dried and the solvent removed. The residue is extracted with pentane and dried to give 3-cyano-4-nitrofluorobenzene (115 g., 86.5%) m.p. 102-104 C.

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

Reference:
Patent; Rohm and Haas Company; US4330324; (1982); A;,
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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. 64113-84-4 name is 2-Fluoro-5-methylbenzonitrile, 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. 64113-84-4

Combine 4-fluoro-2-nitro-phenylamine (2.9g, 18.50 mmol), 2-fluoro-5-methyl- benzonitrile (2. 5g, 18.50 mmol) and lithium hydroxide monohydrate (2.4g, 57.20 mmol) in methyl sulfoxide (DMSO, 40 ml). Heat the resulting mixture to 55 [C] for 40 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture and collect the precipitate. Chromatograph the solid using flash chromatography and elute with mobile phase: 90% hexanes, 5% ethyl acetate, and 5% dichloromethane to obtain 2.267g of the title compound (8.36 mmol, 45% yield) as an orange amorphous solid: Mass Spectrum [(M/E)] : 272 (M+1).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
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876-31-3, 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. 876-31-3, name is 4-(Cyanomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 10 (4 mmol, 1 equiv.), appropriate 4-cyanophenylacetonitrile (5.24 mmol, 1.3 equiv.),and anhydrous DMF (10 mL) was stirred for 0.5 h at 15 C under N2. Then, NaH (13.71 mmol; 60%dispersion in mineral oil, 2 equiv.) was added portion-wise at 15 C. Then, the mixture was stirredat 15 C for another 2 h, warmed to room temperature, and then reacted for 48-72 h (monitored byTLC). The resulting mixture was poured into a saturated ammonium chloride solution. The precipitatewas collected by filtration and the residue was then purified via column chromatography on silica gel,eluting with EtOAc/petroleum ether (1:3) to obtain compounds A1-A12 and B1-B6 as white or yellowsolids. Full characterization data for all final compounds can be found in the Supporting Information. 4-(4-(cyano-(4-cyanophenyl)methyl)-pyrimidin-2-ylamino)benzonitrile (A1) Yield = 87%. mp:243.2-244.7 C. 1H NMR (400 MHz, THF-d8) 9.39 (s, NH), 8.40 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 8.7 Hz,2H), 7.68 (d, J = 8.2 Hz, 2H), 7.58 (d, J = 8.2 Hz, 2H), 7.48 (d, J = 8.7 Hz, 2H), 6.86 (d, J = 5.0 Hz, 1H), 5.53(s, 1H). 13C NMR (101 MHz, THF-d8) 163.6, 159.6, 159.3, 143.8, 139.0, 132.4 (2C), 132.2 (2C), 128.6 (2C),120.3, 118.2 (2C), 117.1, 116.8, 112.5, 110.4, 104.3, 43.5. HRMS (ESI): m/z calcd for C20H12N6 [M H]+335.1051, found 335.1053.

The synthetic route of 876-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Fen-Er; Li, Ting-Ting; Pannecouque, Christophe; Zhuang, Chun-Lin; de Clercq, Erik; Molecules; vol. 25; 7; (2020);,
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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. 4360-47-8, name is Cinnamonitrile, This compound has unique chemical properties. The synthetic route is as follows., 4360-47-8

General procedure: Nitro compound or olefin(5 mmol) and hydrogen source (25 mmol) were dissolved inMeOH (10 mL, 0.5 M). After flushing the column with MeOH,the substrate/reagent solution was pumped through the columnat the specified temperature with a flow rate of 0.108 mL/minby using Vapourtec E-series equipment (with a peristalticpump). Alternatively, a syringe pump can be used. The firstcolumn volume was discarded, the second was collected. Thesolvent was evaporated, the residue added to distilled water (20 mL), and extracted with diethyl ether or dichloromethane(3 ¡Á 15 mL). The combined organic phases were dried overMgSO4, filtered, and the solvent was removed in vacuo.

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; Hutchings, Matthew; Wirth, Thomas; Synlett; vol. 27; 12; (2016); p. 1832 – 1835;,
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31643-49-9, name is 4-Nitrophthalonitrile, 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. 31643-49-9

4-Nitrophthalonitrile or 3-nitrophthalonitrile and 2-propyn-1-ol were dissolved in 10.0mL dry DMSO and stirred at room temperature under nitrogen for 15min. Then anhydrous potassium carbonate (9.83mmol, 0.679g) was added. Dry ground potassium carbonate (2.85mmol, 0.399g) was further added after 3h and again after 24h. After 25h, water (100mL) was added to the reaction mixture. The brownish raw product was extracted with CHCl3, washed with pure water, dried with Na2SO4, and finally the solvent was removed under vacuum. Subsequently the crude product was purified by the column chromatography on silica gel using eluent CHCl3:MeOH (10:1). 2.2.1 Synthesis of 4-(prop-2-ynyloxy)-phthalonitrile (1) (0007) 4-Nitrophthalonitrile (5.78mmol, 1.07g) and 2-propyn-1-ol (6.94mmol, 0.38g) was used to get 1 as a pale-green solid. Yield: 0.921g (88%); m.p. 152-158C. FT-IR (ATR), numax/(cm-1): 3286 (-C?C-H), 3120, 3077 (C-Harom), 2997 (C-Halip), 2230 (C?N), 2135 (C?C), 1594, 1492 (C=Carom), 1256, 1086 (C-O-C). 1H NMR 250MHz (CDCl3) delta: 7.77 (dd, 1H, Harom), 7.38 (t, 1H, Harom), 7.30 (dd, 1H, Harom), 4.82 (d, 2H, -CH2), 2.63 (t, 1H, -C?CH). 13C NMR (CDCl3) delta: 160.41, 135.20, 120.10, 119.90, 117.51, 115.48, 115.12, 108.31, 77.80, 76.14, 56.57. Anal. Calc. for C11H6N2O: C, 72.52; H, 3.32; N, 15.38. Found: C, 72.45; H, 3.25; N, 15.29%. EI-MS (70eV): m/z Calc.: 182.05; Found: 181.07 [M-H]+.

Statistics shows that 31643-49-9 is playing an increasingly important role. we look forward to future research findings about 4-Nitrophthalonitrile.

Reference:
Article; Koyun, Oezge; Goerduek, Semih; Keskin, BahadIr; Cetinkaya, Ahmet; Koca, AtIf; Avciata, Ulvi; Polyhedron; vol. 113; (2016); p. 35 – 49;,
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16588-02-6,Some common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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 4-halonitrobenzene (1.0 equiv), a hydroxyarene, and Cs2CO3 (1.1 equiv) were combined in DMF and the resulting heterogeneous mixture was stirred vigorously at 25-70 C until all 4-halonitrobenzene was consumed (2-24 h). The reaction mixture was diluted with H2O and was adjusted to pH 5 with 2 N HCl (aq). The solution was extracted three times with EtOAc, and the organic layers were combined, washed once with brine solution, dried over MgSO4, filtered and concentrated in vacuo to furnish the desired diaryl ether that was used directly without further purification.

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

Reference:
Article; Taygerly, Joshua P.; McGee, Lawrence R.; Rubenstein, Steven M.; Houze, Jonathan B.; Cushing, Timothy D.; Li, Yang; Motani, Alykhan; Chen, Jin-Long; Frankmoelle, Walter; Ye, Guosen; Learned, Marc R.; Jaen, Juan; Miao, Shichang; Timmermans, Pieter B.; Thoolen, Martin; Kearney, Patrick; Flygare, John; Beckmann, Holger; Weiszmann, Jennifer; Lindstrom, Michelle; Walker, Nigel; Liu, Jinsong; Biermann, Donna; Wang, Zhulun; Hagiwara, Atsushi; Iida, Tetsuya; Aramaki, Hisateru; Kitao, Yuki; Shinkai, Hisashi; Furukawa, Noboru; Nishiu, Jun; Nakamura, Motonao; Bioorganic and Medicinal Chemistry; vol. 21; 4; (2013); p. 979 – 992;,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows., 1080-74-6

A solution of 5′-bromo-3,4′-dihexyl-[2,2′-bithiophene]-5-carbaldehyde (1.39 g, 3.14 mmol), denatured ethanol (75 cm3), pyridine (5 drops) and 3- (dicyanomethylidene)indan-1-one (0.61 g, 3.1 mmol) was stirred at 23 C for 20 minutes. Additional denatured ethanol (50 cm3) was added and the suspension heated at 80 C for 1 hour. The suspension was cooled to 23 C and the solid collected by filtration. The solid was washed with ethanol (50 cm3) then methanol (50 cm3) to give intermediate 5 (1.73 g, 89%) as a dark solid.1H NMR (400 MHz, CD2Cl2) 8.75 (1H, s), 8.62 – 8.70 (1H, m), 7.87 – 7.96 (1H, m), 7.73 – 7.86 (2H, m), 7.64 (1H, s), 7.23 (1H, s), 2.72 – 2.82 (2H, m), 2.60 – 2.68 (2H, m), 1.62 – 1.77 (4H, m), 1.32 – 1.51 (12H, m), 0.86 – 1.02 (6H, m).13C NMR (100 MHz, CD2Cl2) 188.1, 160.2, 147.6, 147.0, 143.6, 140.9, 139.9, 137.2, 136.9, 135.1, 134.6, 134.5, 134.3, 128.9, 125.2, 123.7, 122.9, 114.6, 114.5, 112.6, 69.9, 31.6, 31.6, 30.0, 29.6, 29.5, 29.2, 29.1, 28.9, 22.6, 13.9, 13.8.

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:
Patent; MERCK PATENT GMBH; MITCHELL, William; WANG, Changsheng; D’LAVARI, Mansoor; (163 pag.)WO2020/48939; (2020); A1;,
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4640-67-9, These common heterocyclic compound, 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 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: To a solution of 2 (0.49 g, 1.7 mmol) in ethanol (20 ml) and piperidine (0.5 ml) as a catalyst was added substituted beta-ketonitriles 3a-d (1.7 mmol). The reaction mixture was heated under reflux for (8-10) h and the progress of the reaction was monitored by TLC using benzene/acetone (2:1) as eluent. The solvent was evaporated under reduced pressure; the oil residue was treated with petroleum ether 40-60C (3 x 10 ml) and recrystallized from ethanol to give (4a-d).

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 4640-67-9.

Reference:
Article; El-Borai, Mohamed A.; Rizk, Hala F.; Beltagy, Doha M.; El-Deeb, Ibrahim Y.; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 415 – 422;,
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