Category: nitriles-buliding-blocks

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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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;,
Nitrile – Wikipedia,
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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;,
Nitrile – Wikipedia,
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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;,
Nitrile – Wikipedia,
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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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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;,
Nitrile – Wikipedia,
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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. 939-80-0, name is 4-Chloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 939-80-0

In a flask equipped with a reflux condenser, frans-4-aminocyclohexanol hydrochloride(2.70g, 17.80mmoles) was suspended in iso-propanol (15m1). To this stirred suspension,triethylamine (4,40m1, 31 .49mmoles) was slowly added, followed by 4-chloro-3- nitrobenzonitrile (2.50g, 13.69mmoles). The resulting yellow suspension was heated at 65C for 36h, allowed to cool down to room temperature before water (lOml) was added to the reaction mixture. The resulting precipitate was collected by filtration andsuccessively washed with water and iso-propanol, to yield 4-(((1R,4R)-4- hydroxycyclohexyl)amino)-3-nitrobenzonitrile as a yellow crystalline solid (3 .28g, 12.55mmoles, 92%). The resulting solid was further purified by recrystallization from hot ethanol.mlz 262.2 [MJ-1]+?H NMR (500 MHz, DMSO-d6) oe 8.49 (s, 1H), 8.18 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.1 Hz, 1H), 4.63 (s, 1H), 3.67 (dtd, J = 14.9, 10.4, 4.0 Hz, 1H), 3.57-3.41 (m, 1H), 2.05-1.88 (m, 2H), 1.89-1.75 (m,2H), 1.53-1.19 (m, 4H).

The synthetic route of 939-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; MATHEWS, Neil; WARD, Simon; LUNN, Graham; PARADOWSKI, Michael; GASCON SIMORTE, Jose Miguel; (72 pag.)WO2016/55780; (2016); A1;,
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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 194853-86-6 as follows. 194853-86-6

General procedure: The mixture of 60% dispersion of NaH (80.0 mg, 2.0 mmol) inmineral oil and 5-bromo-tetrahydroquinoline (3) (212.0 mg,1.0 mmol) in dry DMF (4.0 ml) was stirred at 0 C for 30 min. 4-Fluoro-2-(trifluoromethyl) benzonitrile (378.2 mg, 2.0 mmol) wasadded and the mixture was warmed to room temperature. After2 h, the reaction mixture was quenched with cold water andextracted with ethyl acetate. The organic phase was washed withwater twice and then dried over anhydrous Na2SO4, filtered, andconcentrated under vacuum. Pure 4-(5-bromo-3,4-dihydroquinolin 1(2H)-yl)-2-(trifluoromethyl)benzonitrile (6)was obtained as a yellow solid (100.0 mg, yield 26.2%) after flashcolumn chromatography using a solvent of 10% ethyl acetate inhexanes. For the synthesis of intermediate 5 and 7, commerciallyavailable 2 and 4 were used respectively by the proceduredescribed for intermediate 6.

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
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Adding a certain compound to certain chemical reactions, such as: 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, 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 127667-01-0, 127667-01-0

To a solution of 2-fluoro-5-methoxybenzonitrile (2 g, 13.2 mmoi) in DMSO (6.6 mL) was added l 02 (1.6 mL) and K2C03 (274 mg, 1.98 mmoi). The resulting solution was stirred for 30 mm at it. The reaction was then quenched with NaHC03 (said, 30 mL). The resulting solution was extracted with EtO Ac (50 mL), and the organic layers were combined, and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% EtO Ac/petroleum ether) on silica gel to obtain compound 36a as a white solid. ^I-NM (400 MHz, DMSQ-t delta (ppm): 7.66 – 7.70 (m, 2H), 7.04 – 7.23 (m, 3H), 3.77 (s, 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-Fluoro-5-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (219 pag.)WO2017/27309; (2017); A1;,
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Adding some certain compound to certain chemical reactions, such as: 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, 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 327056-73-5. 327056-73-5

STEP A A mixture of 3-chloro-5-fluoro-benzonitrile (1.1 g, 7.07 mmol), 1-methyl-piperazine (1.18 ml, 10.6 mmol), and K2CO3 (2.92 g, 21.21 mmol) in DMSO (25 ml) was heated to 100C overnight and then partitioned between water and Et2O. The aqueous phase was extracted with Et2O and the collected organic phases were dried over Na2SO4 and evaporated under vacuum. The residue was dissolved in Et2O and extracted with 0.5 M HCl. The aqueous phase was basified with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to give 1.01 g of 3-chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile. Y=61%

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 3-Chloro-5-fluorobenzonitrile.

Reference:
Patent; DAC S.r.l.; EP2033956; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts