Tag: M.W=100-200

Application of 33143-29-2, 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. 33143-29-2 name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, 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.

General procedure: For NaIO4/imidazole system, the reaction was carried out with alkene (1 mmol), n-nonane (internal standard, 1 mmol), NaIO4 (2 mmol) and the catalyst (5% mmol) at 25 C for 5 h in the 2:1 mixture of acetonitrile : water. The catalyst was precipitated from the reaction mixture by adding hexane (10 mL), and then the organic phase was separated and purified on a silica gel column, and then analyzed by GC. The progress of the reaction was monitored by GC to find the optimal conversion and selectivity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Dimethyl-2H-chromene-6-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Huang, Jing; Liu, Sirui; Ma, Yan; Cai, Jiali; Journal of Organometallic Chemistry; vol. 886; (2019); p. 27 – 33;,
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These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. Recommanded Product: 4-Cyano-3-trifluoromethylaniline

To a solution of 4-amino-2- (trifluoromethyl) benzonitrile(XVII-I) (1.6 eq.) in THF (8.5 mL x mmol), cooled at -100C,LHMDS (4.5 eq.) was added drop wise. The reaction mixture was than stirred at this temperature for 40 min and HMPA(10% of the total THF) was added to the solution. After 5 min stirring, a solution of the ester XVIII-I (1 eq.) in THF (7 mL x mmol) was added to the reaction mixture. After 30 min at -100C, the solution was stirred 12h at room temperature. The reaction mixture was than quenched with 0. IN HCl and extracted with EtOAc. The crude material was purified by silica gel column chromatography. Yields range from 60 to 80%.(.R) -XXIV-3: 1H NMR (400 MHz, CDCl3) : 8.53 (broad s, IH) 7.63-7.72 (m, 2H), 7.50-7.55 (m, IH), 7.34-7.40 (m, 2H), 7.15-7.19 (m, 5H), 6.87 (dd, J= 8.8 Hz, IH) 3.87 (d, J= 14.4 Hz, IH), 3.45 (s, IH) . 3.22 (d, J= 13.6Hz, IH), 3.11 (d, J= 13.6Hz, IH), 2.95 (d, J= 14.4Hz, IH, CH2) . 13C NMR (100 MHz, CDCl3) Relevant: 172.1, 161.8 (d, J= 248Hz) 141.0,135.8, 134.5, 134.2 (d, J= 8.5Hz), 130.5, 128.8, 127.7, 122.6 (q) , 122.0, 117.6 (q, J= 5Hz) , 116.5 (d, J= 22.1Hz) 115.6, 105.0.

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; ISTITUTO SCIENTIFICO ROMAGNOLO PER LO STUDIO E LA CURA DEI TUMORI (I.R.S.T.) S.R.L.; VARCHI, Greta; TESEI, Anna; GUERRINI, Andrea; BRIGLIADORI, Giovanni; WO2010/116342; (2010); A2;,
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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. 873-74-5, name is 4-Aminobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Aminobenzonitrile

General procedure: A mixture of amine 1 (0.50 mmol), 1,3-diketone 2 (0.60 mmol, 1.2 equiv), iodine(12.7 mg, 0.05 mmol, 10 mol%) and TsOHH2O (19.0 mg, 0.10 mmol, 20 mol%) in 1,4-dioxane (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature.The mixture was stirred at 140 C until the reaction was finished. Then, the solvent wasevaporated under reduced pressure and the residue was purified by column chromatography(petroleum ether/ethyl acetate 5:1 to 2:1) to afford the product 3.

According to the analysis of related databases, 873-74-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhou, Xiao-Yu; Chen, Xia; Yang, Dan; Synthetic Communications; vol. 50; 2; (2020); p. 177 – 184;,
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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, category: nitriles-buliding-blocks

Dissolve sodium metal (0.345 g) in absolute EtOH (25 mL), add diethyloxalate (10 mL) and then add 4-methyl-3-nitrobenzonitrile (lb, m=0, 1.6 g, Aldrich) as an EtOH solution (25 mL). Stir the reaction mixture at rt for 16 hours, neutralize the reaction by addition of 5N HC1 (3 mL) and remove the EtOH under reduced pressure. Partition the residue between CH2C12 (100 mL) and H20 (50 mL). Wash the organic layer successively with H20 (50 mL) and brine (50 mL), dry (MgSO4) and concentrate to give a crude oil. Purify the oil by chromatography on SiO2 eluting with cyclohexane-EtOAc, 70-30 v/v, to afford gave after drying (40C, house vacuum), the title compound (1.5 g) as yellow crystals, mp 118 C.

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; AVENTIS PHARMACEUTICALS INC.; WO2006/23467; (2006); A1;,
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Synthetic Route of 67832-11-5, A common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, molecular formula is C8H6BrN, 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.

EXAMPLE 164A 4′-methoxy-3-methyl-1,1′-biphenyl-4-carbonitrile 4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75 C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3*40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85 % yield). 1H-NMR (300 MHz, CDCl3) delta 2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (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; Bennani, Yousseff L.; Faghih, Ramin; Dwight, Wesley J.; Vasudevan, Anil; Conner, Scott E.; US2002/137931; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 939-80-0, name is 4-Chloro-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 939-80-0, name: 4-Chloro-3-nitrobenzonitrile

[0188] A solution of 4-(2,4-difluorophenoxy)piperidine (0.640 g, 3 mmol), 4-chloro-3- mtrobenzomtriie (0.657 g, 3.60 mmol), and K2CO3 (0.829 g, 6.00 mmol) in DMSO (9.09 mL) was stirred at 80C overnight. The reaction mixture was subsequently partitioned between EtOAc and water. The organic layer was washed twice with water and dried over anhydrous NaiSO-t. The solvent was evaporated to give the title compound as an off-white solid, which was used without further purification. ESI-MS m/z [M+H] 360.2.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 368-77-4, name is 3-(Trifluoromethyl)benzonitrile, 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 368-77-4, Product Details of 368-77-4

A suspension of 3-(trifluoromethyl)benzonitrile (16c) (2.35 mL, 17.53 mmol, 1.00 equiv), hydroxylamine hydrochloride (1.58 g, 22.79 mmol, 1.30 equiv) and sodium carbonate (2.42 g, 22.79 mmol, 1.30 equiv) in ethanol (abs, 20 mL) was heated to reflux for 22 h. After 3 h, further hydroxylamine hydrochloride (1.30 equiv) and sodium carbonate (1.30 equiv) were added. The inorganic solids were removed by filtration and the solvent was removed in vacuum to give 3.60 g of a colorless oil that solidifies over time (quant.). 26 1H NMR (250 MHz, CDCl3): delta = 7.90 (s, 1H, 2H-ph-CF3), 7.82 (d, 1H, 3J = 7.8 Hz, 4H-ph-CF3), 7.68 (d, 1H, 3J = 7.8 Hz, 6H-ph-CF3), 7.53 (t, 1H, 3J = 7.8 Hz, 5H-ph-CF3), 4.92 (br s, 2H, NH2), 1.89 (s, 1H, -OH); ESI-MS: m/z = 204.6 [M+H]+.

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; Flesch, Daniel; Gabler, Matthias; Lill, Andreas; Gomez, Roberto Carrasco; Steri, Ramona; Schneider, Gisbert; Stark, Holger; Schubert-Zsilavecz, Manfred; Merk, Daniel; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3490 – 3498;,
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Electric Literature of 455-18-5,Some common heterocyclic compound, 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

[Preparation Example 1] Preparation of Compound III-2a [Show Image][Step H] Selenium powder (3.95 g, 50 mmol) was added to ethanol (50 mL) under nitrogen atmosphere. Then, sodium borohydride (2.02g, 53 mmol) wascautiouslyaddedslowlyfor30minutes (Hydrogen gas was produced.). To the resultant ethanolic sodium hydrogen selenide, 4-(trifluoromethyl)benzonitrile (11.9 g, 70 mmol) and pyridine (8 mL) were added. Then, 2 M hydrochloric acid (25 mL) was slowly added dropwise for 1. 5 hours while refluxing at 80 C. After further stirring for about 30 minutes, the precipitated target compound was filtered and washed with hexane and water. Recrystallization using benzene solvent yielded Compound III-2a (15.1 g, yield: 91 %) as yellow solid. 1H NMR (300 MHz, CDCl3) delta 11.07 (b, 1H), 10.43 (b, 1H), 7.99 (d, 2H, J = 8.5 Hz), 7.77 (d, 2H, J = 8.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; SNU R & DB Foundation; EP2540711; (2013); 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. 14447-18-8, name is Benzyl cyanoacetate, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester: To a mixture of 2,2,6-Trimethyl-heptanal (1.05 g, 6.73 mmol), piperidine (0.19 mL, 2.01 mmol) and benzyl cyanoacetate (1.29 g, 7.4 mmol) in toluene (50 mL) was added glacial acetic acid (0.72 g, 12.1 mmol). The flask was fitted with a Dean-Stark trap, and the mixture was heated at reflux for 18. The mixture was cooled, treated with dilute HCl, and the layers were separated. The organics were washed with a saturated sodium bicarbonate solution followed by brine, and dried (MgSO4), filtered and concentrated. The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc) to give 1.3 g of 2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester m/z 314 (M+).

The synthetic route of 14447-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Field, Mark John; Williams, Richard Griffith; US2004/157847; (2004); A1;,
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Application of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

Step D. 2-[1-(2-Cyano-4-nitro-phenyl)-piperidin-4-yl]-N-ethyl-2-phenyl-acetamide. To a solution of N-ethyl-2-phenyl-2-piperidin-4-yl-acetamide (500 mg, 2 mmol) and 2-fluoro-5-nitro-benzonitrile (337 mg, 2.03 mmol) in DMF was added K2CO3 (840 mg, 6.1 mmol). The solution was heated to 80 C. for 16 h. After cooling to rt, H2O and 3:1 EtOAc/hexanes were added. The organic portion was washed three times with H2O and once with brine, dried (Na2SO4) and concentrated to provide the title compound (yellow powder, 686 mg, 86%).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); A1;,
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