Nitriles-buliding-blocks

A common compound: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1080-74-6

The specific operation is as follows: adding the above dialdehyde structural compound 17 (0.20 g) to a 100 mL two-necked bottle,The terminal group 1 (0.21 g), 40 ml of dry chloroform and pyridine (1 ml) were reacted at room temperature for 24 hours.The organic phase was extracted with chloroform, dried over anhydrous sodium sulfate and evaporated.Column chromatography separationBlue-black solid compound 6 (0.25 g, yield 84%).

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, 1080-74-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nankai University; Chen Yongsheng; Qiu Nailiang; Zhang Huijing; Feng Huanran; (32 pag.)CN108864135; (2018); A;,
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A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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. 1080-74-6.

EXAMPLE 11 Cvclization to Form Dihvdropyridine 16 (R = 2-fury, R3=H) To a solution of 3-dicyanovinylindan-1-one (4.06 g, 20.9 mmol) in 200 mL of ethanol was added 2-furaldehyde (3.01 g, 31.4 mmol) and 25 mL of conc. NH40H. The solution was heated to reflux for 2 h and allowed to cool to rt overnight. The mixture was concentrated in vacuo to remove ethanol. The residue was filtered and washed with water. The purple solid obtained was dried to yield 5.92 g (89%).

The synthetic route of 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORTHO-MCNEIL PHARMACEUTICAL, INC.; WO2005/42500; (2005); A1;,
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1558-81-2, A common heterocyclic compound, 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, molecular formula is C7H9NO2, 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 mixture of ethyl 1-cyanocyclopropanecarboxylate (35.9 mmol, 5 g), dimethoxyethane (100 mL) and methanol (10 mL) was added sodium borohydride (287 mmol, 10.87 g) slowly and the mixture stirred at room temperature for 18 hours. The solution was diluted with saturated sodium hydrogen carbonate slowly and then extracted with 10% methanol/dichloromethane (*3). The organic layers were combined, dried over sodium sulphate and concentrated under vacuum to give the intermediate 1-(hydroxymethyl)cyclopropanecarbonitrile (2.36 g). 1H NMR (CDCl3, 400 MHz): delta 0.99 (2H, m), 1.28 (2H, m), 2.5 (1H, br s), 3.62 (2H, s)

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

Reference:
Patent; N.V. Organon and pharmacopeia, Inc.; US2009/264416; (2009); A1;,
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16588-02-6, Adding some certain compound to certain chemical reactions, such as: 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, 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 16588-02-6.

3-Cyano-4-chloroaniline 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

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 16588-02-6.

Reference:
Patent; Pierson, Edward; Sohn, Daniel; Haeberlein, Markus; Davenport, Timothy; Chapdelaine, Marc; Horchler, Carey; McCauley, John P.; US2003/13708; (2003); A1;,
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78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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. 78473-00-4

Method 2: Example 19: 3^-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitri Step 1 : 4-{[l-(4-Azidopyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile Triethylamine (8.9 mL, 64.2 mmol) was added to a cooled (0 C) mixture of 4-azidopyridine-3-carbaldehyde (3.2 g, 21.4 mmol) and 4-amino-3,5-dichlorobenzonitrile (4.0 g, 21.4 mmol) in DCM (80 mL) under nitrogen. Titanium tetrachloride (1M, 12.8 mL, 12.8 mmol) was added and then the reaction mixture was stirred for 1 hour at 0 C. After warming to room temperature, the reaction was stirred for an additional 2 h and then concentrated under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as an orange solid. This crude material was employed in the next step without further purification or analysis.

Statistics shows that 78473-00-4 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3,5-dichlorobenzonitrile.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLENCH, Toby; GOODACRE, Simon; LAI, Yingjie; LIANG, Yun; MACLEOD, Calum; MAGNUSON, Steven; TSUI, Vickie; WILLIAMS, Karen; ZHANG, Birong; WO2012/66061; (2012); 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. 2032-34-0, name is 3,3-Diethoxypropanenitrile, A new synthetic method of this compound is introduced below., 2032-34-0

A mixture of 3,3-diethoxypropanenitrile (1.80 mL, 12.00 mmol), 2-amino-4-bromobenzaldehyde (2g, 10.00 mmol) and p-toluenesulfonic acid monohydrate (0.380 g, 2.000 mmol) in toluene (30 mL) was heated under reflux using Dean-Stark apparatusfor 3 h. The reaction was cooled, evaporated under reduced pressure, and the residue was dissolved in a small amount of N,N-dimethylformamide, diluted with chloroform, and washed with aq sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined extracts were washed with brine, dried (Na2504), and concentrated in vacuo. Purification of the residue by flash chromatography (0-3%methanol in dichloromethane) followed by trituration in diethyl ether provided the titlecompound (1.75 g, 75%). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.95 (dd, J=8.72, 1.89Hz, 1H) 8.08 (d, J=8.84 Hz, 1H) 8.38 (d, J=2.02 Hz, 1H) 9.13 (d, J=1.52 Hz, 1H) 9.21(d, 1H).

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; GLAXOSMITHKLINE LLC; MOORE, Michael, Lee; PARRISH, Cynthia, Ann; SQUIRE, Michael, Damien; WO2013/52716; (2013); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3598-14-9, name is Phenoxyacetonitrile, 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 3598-14-9, 3598-14-9

Diisobutylaluminum hydride (DIBAL-H, 1. OM in toluene, 20.0 mL) is added dropwise to a stirred solution OF PHENOXYACETONITRILE (2.22 g, 16.7 mmol) in anhydrous CH2CL2 (18 mL) at-78 C under nitrogen. The resultant solution is allowed to stir at 0 C for 1 hour. Methanol (2 mL) is added dropwise to quench excess of DIBAL-H, followed by the successive addition of Et2O (40 mL) and 2N HCl (60 mL) in small portions to the cold mixture. The resultant two-layered solution is allowed to stir vigorously at ambient temperature for 1 hour. Ethyl ether (30 mL) and saturated aqueous NACL solution (30 ML) are added to the mixture. The organic layer is separated, dried over MGS04, filtered and concentrated at ambient temperature to give 2.27 g of the crude phenoxyacetaldehyde as oil. The oil is diluted in Et2O to form a stock solution (60 mg/mL), which is used for the subsequent REACTION. 1H NMR (CDC13) : W4. 57 (s, 2H), 9.87 (s, 1H). A 6.06 mL of the above stock solution (No.1.1 mmol) is added to a stirred mixture of 4A molecular sieve (600 mg) and isoquinoline-5-solfonic acid (2-amino-ethyl)-amide (244 mg, 0.971 mmol) in anhydrous CH30H (5 ML), and the resultant mixture is stirred at ambient temperature for 16 hours. The mixture is cooled to 0 C before it is treated with powdered sodium borohydride (81 mg, 2.1 mmol). The mixture is stirred at 0 C for 1 hour then at ambient temperature for another 1 hour. After filtration and subsequent concentration in vacuo, the crude product is chromatographed on silica (gradient 5-30% CH30H in EtOAc) to give 156 mg (0.420 mmol, 43% yield) of the free amine product as oil. The free amine (154 mg, 0.415 mmol) is dissolved in EtOAc (15 mL) and treated dropwise with 1N HCI/ETZO solution (1.24 mL) with stirring under nitrogen. The white suspension is stirred for 15 minutes, filtered and dried under vacuum at 60 C to give 177 mg (0.398 mmol, 96% yield) of the title compound as a hygroscopic white powder. ESIMS: m/z 372 (M+H) +.

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, Phenoxyacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94386; (2004); A1;,
Nitrile – Wikipedia,
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194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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. 194853-86-6

To a solution of 4-fluoro-2-(trifluoromethyl)benzonitrile (2.0 g) in ethanol (10.0 mL) was added Raney Ni (catalytic amount). The reaction mixture was subjected for hydrogenation in Parr apparatus under 50 psi for 2-3 h. The reaction mass was filtered through celite and the filtrate was concentrated to afford 0.400 g of desired product. 1HNMR (CDCl3): delta 3.98 (s, 2H), 7.24 (t, J – 9.0 Hz, 1H), 7.34 (d, – 8.7 Hz, 1H), 7.54 (t, J = 7.8 Hz, 1H); MS [M+H]+ : 194.03.

Statistics shows that 194853-86-6 is playing an increasingly important role. we look forward to future research findings about 4-Fluoro-2-(trifluoromethyl)benzonitrile.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/186692; (2013); A1;,
Nitrile – Wikipedia,
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A common compound: 17626-40-3, name is 3,4-Diaminobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 17626-40-3

5.0 g (37.56 mmol) of 3,4-diaminobenzonitrile was dissolved in 20 ml of trifluoroacetic acid, the reaction was refluxed under nitrogen atmosphere for 10 hours, then sinking into water, the filtrate was collected by filtration, washed three times with water, and dried to give 4.91 g (62.0% yield)

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, 17626-40-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chen Yaoteng; Huang Bingzhao; Zheng Zhilong; Chen Siyuan; Wei Anxing; (19 pag.)CN103896849; (2017); B;,
Nitrile – Wikipedia,
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67832-11-5, 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, A new synthetic method of this compound is introduced below.

4-bromo-2-methylbenzonitrile (1 mmol) was suspended in water (49 mL) and potassium hydroxide was added (50 mmol); the reaction mixture was stirred at reflux overnight. After cooling, the basic solution was washed with ethyl acetate (3 x 15 mL), acidified with hydrochloric acid (6M) and extracted with ethyl acetate (3 x 15 mL). The organic phase deriving from the acidic extraction was dried over anhydrous sodium sulfate and concentrated in vacuo, yielding the desired product as a white solid. Yield: 60%. TLC (dichloromethane – methanol 9:1): Rf = 0.46. Mp: 182C. 1H-NMR (300 MHz, CD3OD) delta (ppm) 7.80 (d, J = 8.4 Hz, 1H, H6), 7.48 (s, 1H, H3), 7.42 (d, J = 8.4 Hz, 1H, H5), 2.56 (s, 3H, CH3).

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:
Article; Chiarelli, Laurent R.; Mori, Matteo; Barlocco, Daniela; Beretta, Giangiacomo; Gelain, Arianna; Pini, Elena; Porcino, Marianna; Mori, Giorgia; Stelitano, Giovanni; Costantino, Luca; Lapillo, Margherita; Bonanni, Davide; Poli, Giulio; Tuccinardi, Tiziano; Villa, Stefania; Meneghetti, Fiorella; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 754 – 763;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts