Category: nitriles-buliding-blocks

Synthetic Route of 4513-77-3, These common heterocyclic compound, 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, 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.

To a solution of triphenylphosphine (29.9 g, 114 mmol) in 500 ml_ of THF, cooled to 0 0C, was slowly added a 40% solution of diethyl azodicarboxylate in toluene (52.2 ml_, 114 mmol), ethyl glycolate (10.8 ml_, 114 mmol) and 2- oxocyclohexanecarbonitrile (10 g, 81.3 mmol). The resulting solution was stirred at room temperature for 20 hours. Then 50% sodium hydride (11 g, 229 mmol) was added and the mixture was stirred at room temperature for 5 hours. The reaction mixture was cooled to 0 0C and a pH 7.8 phosphate buffer (Na2HPO4/KH2PO4) solution (375 ml_) was added. THF was evaporated and the resulting aqueous solution was extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The resulting crude product was chromatographed on silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 8.5 g of the desired compound (yield: 50%). LC-MS (Method 2): tR = 1.97 min; m/z = 210 (MH+).

Statistics shows that 2-Oxocyclohexanecarbonitrile is playing an increasingly important role. we look forward to future research findings about 4513-77-3.

Reference:
Patent; PALAU PHARMA, S. A.; WO2009/56551; (2009); A1;,
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Electric Literature of 4513-77-3, 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. 4513-77-3, name is 2-Oxocyclohexanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-oxocyclohexanecarbonitrile (250 mg, 2.03 mmol) in EtOH (20 mL) was added CHCI3 (1 mL) and Pt02 (55.3 mg, 0.244 mmol) and the reaction mixture was stirred under hydrogen atmosphere (3 atm) for 67 h. Subsequently the reaction mixture was filtered over Celite and 4N HCI in dioxane was added to the filtrate, which was then concentrated to afford the title compound. The product was used in the next step without further purification.

The synthetic route of 2-Oxocyclohexanecarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige, Liliane, Jeanne; MAIBAUM, Juergen, Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan, Andreas; VULPETTI, Anna; WO2014/2054; (2014); A1;,
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Electric Literature of 268734-34-5, 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 268734-34-5 as follows.

To a solution of ethanehydroxamic acid (0.629 g, 8.37 mmol) in DMF (5 ml.) was added potassium 2-methylpropan-2-olate (0.94 g, 8.4 mmol) and the reaction was stirred for 30 minutes. Methyl 4-cyano-3-fluorobenzoate (1.0 g, 5.6 mmol) was added followed by DMF (2 ml.) and the reaction was stirred for a further 2 hours at room temperature. The reaction was diluted with ethyl acetate (50 ml.) and water (50 ml_), the aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, dried, filtered and concentrated. The crude material was purified by silica gel chromatography (12 g Si02 cartridge, 0-50% EtOAc in petroleum benzine 40-60 C) to give the title compound (0.55 g, 51% yield) as a white solid. 1H NMR (400 MHz, CDCIs) d 8.12 (d, J = 1.02 Hz, 1H), 7.96 (dd, J = 1.24, 8.29 Hz, 1H), 7.59 (dd, J = 0.77, 8.25 Hz, 1H), 3.98 (s, 3H). LCMS: rt 2.97 min, m/z 193.0 [M+H]+.

According to the analysis of related databases, 268734-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
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Application of 6575-05-9,Some common heterocyclic compound, 6575-05-9, name is 2,4,6-Trichlorobenzonitrile, molecular formula is C7H2Cl3N, 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.

Add 2,4,6-trichlorobenzonitrile (206 mg, 1.0 mmol) to 96% formic acid (5 niL, 96%) and water (1 mL). Add nichol/aluminum alloy (206 mg) to the mixture. Heat at 100 0C for 4 hours. Dilute with ethyl acetate and filter through Celite. Extract the filtrate with. N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 2,4,6-trichlorobenzaldehyde (195 mg, 93%). 1H NMR (400 MHz, CDCl3) delta 10.36 (s, IH), 7.99 (s,lH), 7.61 (s, IH).

The synthetic route of 6575-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
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Some common heterocyclic compound, 939-80-0, name is 4-Chloro-3-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. Application In Synthesis of 4-Chloro-3-nitrobenzonitrile

In dry acetonitrile (40 ml) were dissolved 4-chloro-3-nitrobenzonitrile (4.0 g, 21 .98 mmol), ethyl glycinate hydrochloride (4.6 g, 32.97 mmol) and diisopropyl ethylamine (10.9 ml, 65.94 mmol) in microwave vial and the mixture was irradiated at 125 C for 30 minutes. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield 4.0g (73.13%) of the title compound . 1 H- NMR(400MHz,CDCl3)delta: 1.33(t,J=7.2Hz,3H),4.13(d,J=5.2Hz,2H),4.32(q,J=7.2Hz,2H ),6.77 Eta),8.81 (5, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-80-0, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; KATOCH, Rita; INAGAKI, Hiroaki; FUJISAWA, Tetsunori; WO2014/24056; (2014); A1;,
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Some common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, 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. Quality Control of 2-(Cyanomethyl)benzonitrile

General procedure: A mixture of 2-oxo-6-aryl-4-piperidin-1-yl-2H-pyran-3-carbonitrile (1.0 mmol), 2-cyanomethylbenzonitrile (1.0mmol, 142.0 mg), and NaNH2 (2.0 mmol, 78.0 mg) in dryDMF (2.0 mL) was heated at 100 C for 55 min undermicrowave irradiation. Completion of reaction wasmonitored by TLC. After completion, the reaction mixturewas poured onto crushed ice and neutralized with 10% HCl.The precipitate obtained was filtered, washed with H2O,dried, and purified by silica gel column chromatographyusing hexane-EtOAc (7:3) as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3759-28-2, its application will become more common.

Reference:
Article; Singh, Surjeet; Yadav, Pratik; Sahu, Satya Narayan; Sharone, Ashoke; Kumar, Brijesh; Ram, Vishnu Ji; Pratap, Ramendra; Synlett; vol. 25; 18; (2014); p. 2599 – 2604;,
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Reference of 3218-50-6, 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. 3218-50-6, name is 2,5-Dichlorobenzyl cyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,5-dichlorobenzyl bromide (5.4 g, 22.5 mmol) in 16 mL of ethanol and potassium cyanide (1.63 g, 25 mmol) in 4 mL of water was heated at 80 C overnight, then cooled, and the solids were filtered and washed with ethanol to give 3.5 g of 2,5- dichlorophenylacetonitrile as a white powder melting at 89-91 C. The nitrile was suspended in 20 mL of ethanol, and 20 mL of a 25 % aqueous NaOH solution was added.The mixture was heated in a CEM Explore microwave reactor at 140 0C for 30 minutes, then cooled, poured into ice water and acidified to pH 1 with concentrated HCl to give a precipitate. The precipitate was filtered, washed with water and dried in a vacuum oven at90 0C for 5 h to give the title compound as a white powder. 1H NMR (CDCl3) 5 3.79 (s, 2H), 7.2-7.4 (m, 3H)

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, 2,5-Dichlorobenzyl cyanide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/91594; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, 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 76469-88-0, Recommanded Product: 76469-88-0

Referential Example 57 Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate Methyl 4-cyanomethylbenzoate (0.20 g) was dissolved in a mixed solvent of methanol (15 ml) and chloroform (0.4 ml). To the resulting solution, platinum dioxide (33 mg) was added, followed by catalytic reduction at room temperature under 3 atmospheric pressure for 3 hours. The catalyst was removed by filtration through Celite and the solvent was distilled off under reduced pressure. The residue was suspended in dichloromethane (5 ml), followed by the addition of triethylamine (160 mul). After the addition of a solution of di-tert-butyl dicarbonate (0.29 g) in dichloromethane (dichloromethane: 2 ml) under ice cooling, the resulting solution was stirred at room temperature for 13 hours. The reaction mixture was diluted with dichloromethane, washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate 10:1~5:1), whereby the title compound (0.28 g, 88%) was obtained. 1H-NMR (CDCl3) delta: 1.43(9H,s), 2.86(2H,t,J=6.8 Hz), 3.39(2H,m), 3.91(3H,s), 4.53(1H,br), 7.27(2H,d,J=8.3 Hz), 7.98(2H,d,J=8.3 Hz).

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; Daiichi Pharmaceutical Co., Ltd.; US6525042; (2003); B1;,
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Synthetic Route of 626-17-5, A common heterocyclic compound, 626-17-5, name is 1,3-Dicyanobenzene, molecular formula is C8H4N2, 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 40 Isophthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and methanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130 C. for seven hours. The reaction mixture was cooled, and water (9 g) was added thereto. Gas chromatographic analysis revealed that methyl m-cyanobenzoate had been produced at a yield of 38% and a selectivity of 83%.

The synthetic route of 626-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Oxobutanenitrile

Step 3. 2-Benzyl-3-oxobutanenitrile To a solution of Na (1.17 g, 50.87 mmol) in EtOH (20 mL) was added 3-oxobutanenitrile (2.5 g, 30.09 mmol) and (bromomethyl)benzene (5 g, 29.23 mmol), and the reaction mixture was stirred for 2 hours at 80 C. The resulting mixture was concentrated in vacuo, diluted with water (200 mL), adjusted to pH 6 with HCl (3N), extracted with ethyl acetate (3*100 mL), dried over anhydrous magnesium and concentrated in vacuo to provide a residue, which was purified via silica gel column chromatography with 1.25% to 5% ethyl acetate in petroleum ether to afford 2-benzyl-3-oxobutanenitrile as a brown solid (2 g, 39%). LC/MS (ES, m/z):[M+H]+ 174.1

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 2469-99-0.

Reference:
Patent; BIOENERGENIX; US2012/277224; (2012); A1;,
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