Category: nitriles-buliding-blocks

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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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 90110-98-8 as follows. Recommanded Product: 90110-98-8

1.4 (Z)-3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine (1-3) Hydroxylamine hydrochloride (0.524 g, 7.54 mmol) and sodium bicarbonate (1.27 g, 15.08 mmol) were added successively to a solution of 3-bromo-4-hydroxymethyl benzonitrile (1-2, 0.80 g, 3.77 mmol) in methanol (120 mL) to obtain a suspension which was then heated to reflux for 5 hours. It was then cooled down to room temperature and filtered. The filter cake was washed with methanol (10 mL), and the filtrate was concentrated to obtain 3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine which was a white crude product (1-3, 0.90 g, 97% yield), which was directly used in the next step. The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 245/247 [M+H]+.

According to the analysis of related databases, 90110-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUZHOU CONNECT BIOPHARMACEUTICALS, LTD.; ZHENG, Wei; PAN, Wubin; YANG, Xin; (47 pag.)EP3048103; (2016); A1;,
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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.

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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.

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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]+.

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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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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. 3108-23-4, name is 4,4,4-Trifluoro-2-(4-fluorophenyl)-3-oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3108-23-4

Reagents and conditions: (a) EtONa, EtOH, refluxing; (b) CH3NHNH2, HC1, EtOH,MW, 100C, 40 mm; (c) Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride,DCM, then DBU. A mixture of 1.8 ml (15 mmol) of ethyl 2,2,2-trifluoroacetate (ib)and 0.96 g (7.1 mmol) of 2-(4-chloro-2-fluorophenyl)acetonitrile (3a) in 10 ml ofethanol was slowly dropped into hot solution of 1.2 g of sodium in 20 ml of ethanol.The mixture was refluxed overnight. The solution turns red. After cooled down, thesolution was poured into 250 ml of cold water acidified with 10 ml concentrated HC1.The mixture was extracted with ethyl acetate. The ethyl acetate extraction was washedwith water, brine and dried over Mg504. Ethyl acetate was removed and the residualreddish oil of 4,4,4-trifluoro-2-(4-fluorophenyl)-3 -oxobutanenitrile (3c) was obtained in1.3 g. The raw material was dissolved in 10 ml of ethanol and used in next step withoutfurther purification. A mixture of 2.8 ml of the above ethanol solution and 125pi ofmethylhydrazine with 0.2 ml of concentrated HC1 was irradiated in microwave oven at100C for 40 mm. The solution was treated with saturated NaHCO3 and extracted byethyl acetate. The organic layer was washed with water, brine, dried over Mg504 andconcentrated. The yellow residue was subjected to flash chromatography purificationwith MeOHIDCM to give 165 mg of 3-(trifluoromethyl)-4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-amine (3d) as light yellow solid. ?H NMR (500 MHz, CDC13) 7.32 (s,2H), 7.14 (t, J = 8.0 Hz, 2H), 3.76 (d, J = 33.5 Hz, 3H), 3.65 (s, 2H). M/Z =260.6(M+1). To a solution of Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoyl chloride (43mg, 0.20 mmol) produced from Fmoc-(R)-3-amino-4-(4-fluorophenyl)butanoic acid(from Chem Impex International) and thionyl chloride in 10 ml of anhydrous DCM were slowly added 3 -(trifluoromethyl)-4-(4-fluorophenyl)- 1-methyl-i H-pyrazol-5 – amine obtained as described above (39 mg, 0.15 mmol) in 5 ml of anhydrous DCM. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with methanol and solvents were removed. The residue was purified via silicagel with MeOHIDCM to obtained Fmoc protected product. Fmoc protected product was dissolved in 10 ml of ethyl acetate and 0.15 mmol of DBU was added. After 20mm 20 ml of ethyl acetate was added and mixture was washed with 20 ml of water. The organic layer was collected and solvent was removed. The residue was dissolved in MeOH and acidified with 0.2N HC1. The solution was purified via preparatory RP-HPLC, elutingwith H20/CH3CN gradient (+0.05% TFA). Product fractions are collected and concentrated. The residue is dissolved in a small amount of 2M HC1 in methanol and, after concentration in vacuo, 50 mg of Compound (3) is obtained as an HC1 salt. ?H NIVIR (500 IVIFIz, MeOD) 7.40 – 7.08 (m, 6H), 7.02 (t, J = 8.8 Hz, 2H), 3.77 (d, J = 15.4 Hz, 3H), 3.37 (dt, J = 7.9, 6.6 Hz, 1H), 2.64 (m, 2H), 2.42 (m, 2H). M/Z 439.4(M+i).

The synthetic route of 3108-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MMV MEDICINES FOR MALARIA VENTURE; DREXEL UNIVERSITY; UNIVERSITY OF WASHINGTON; BURROWS, Jeremy; WYVRATT, Matthew; VAIDYA, Akhil; KORTAGERE, Sandhya; FAN, Erkang; CHATTERJEE, Arnab Kumar; NAGLE, Advait Suresh; KATO, Tomoyo; WO2015/8246; (2015); A1;,
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