Month: September 2021

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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 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%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
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Related Products of 1080-74-6,Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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 degassed solution of intermediate 1 (0.13 g, 0.1 1 mmol) and 3- (dicyanomethylidene)indan-l -one (1 .5 g, 0.77 mmol) in chloroform (12 cm3) is added pyridine (0.6 cm3, 8 mmol). The mixture is then degassed with nitrogen for 30 minutes and then heated at 70 C for 15 hours. The reaction mixture allowed to cool to 23 C and the solvent removed in vacuo. The crude is purified by column chromatography (40-60 petrol :chloroform; 1 : 1 ) to give compound 75 (1 .1 g, 65%) as a dark blue crystalline solid. 1H NMR (400 MHz, CDCIs) 8.87 (2H, s), 8.69 (2H, d, J 7.6), 7.91 (2H, d, J 7.1 ), 7.68 – 7.79 (6H, m), 7.08 – 7.18 (16H, m), 2.60 (8H, t, J 7.7), 1 .62 (8H, q, J 7.1 Hz), 1 .21 – 1 .39 (40H, m), 0.88 (12H, t, J 6.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
Nitrile – Wikipedia,
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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 51762-67-5 as follows. Recommanded Product: 51762-67-5

3-nitrophthalonitrile (0.500 g, 2.888 mmol) was dissolved in anhydrous dimethylformamide (75 mL) under Ar and hydroxymethyl-EDOT (0.500 g, 2.903 mmol) was added. After stirring for 10 min, finely ground anhydrous K2CO3 (1.200 g, 8.682 mmol) was added in portions over 2 h with efficient stirring. The reaction mixture was stirred at room temperature for 120 h under Ar. Then the solution was poured into ice-water. The resulting white solid was collected by filtration and washed first with water and then with hexane. Yield 0.493 g (57%). Mp: 192 C. FT-IR: numax, cm-1 3116.56 (CH, aromatic), 2963.20 (CH, aliphatic), 2230.15 (C?N). 1H NMR (400 MHz, DMSO-d6, 298 K): delta, ppm 7.88-7.69 (3H, benzene -CH), 6.64 (2H, thiophene -CH), 4.63-4.13 (5H, -CH and -CH2). 13C NMR (400 MHz, CDCl3, 298 K): delta, ppm 160.38, 141.00, 140.83, 135.87, 126.21, 118.72, 115.71, 115.35, 113.48, 103.10, 100.16, 71.49, 68.00, 64.77. GC-MS: m/z 298 [M]+. C15H10N2O3S (298.04): calcd. C 60.39, H 3.38, N 9.39; found C 60.37, H 3.37, N 9.40.

According to the analysis of related databases, 51762-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karada?, Sebahattin; Bozo?lu, Ceyda; Kasim ?ener; Koca, Atif; Dyes and Pigments; vol. 100; 1; (2014); p. 168 – 176;,
Nitrile – Wikipedia,
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328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, 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. Product Details of 328-87-0

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C for 21/2 hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US4063929; (1977); A;,
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Electric Literature of 29509-06-6, A common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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.

Hydroxylamine hydrochloride (10.3 g, 148 mmol) was slowly added to an ice cold solution of NaOH (25.9 g, 645 mmol) in water (73 mL) and the resulting solution was poured into a solution of crude 3-oxo-4-methylpentanenitrile while stirring. The resulting yellow solution was heated at 50 C for 2.5 hours to produce a less dense yellow oil. The warm reaction mixture was immediately extracted with CHCl3 (3 x 100 mL) without cooling. The combined organic layers were dried (MgSO4), and concentrated in vacuo. The resulting oily yellow solid was filtered through a pad of silica (10% acetone/90% CH2Cl2) to afford the desired isoxazole as a yellow solid (11.3 g, 70%): mp 63-65 C; TLC Rf (5% acetone/95% CH2Cl2) 0.19; 1H-NMR (DMSO-d6) d 1.12 (d, J=7.0 Hz, 6H), 2.72 (sept,J=7.0 Hz, 1H), 4.80 (s, 2H), 6.44 (s, 1H); FAB-MS m/z (rel abundance) 127 ((M+H)+; 67%).

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; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1194-02-1, The chemical industry reduces the impact on the environment during synthesis 1194-02-1, name is 4-Fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of BB8: 4-Fluoro-N-hydroxy-benzamidine; To a solution of the 4-fluoro-benzonitrile (10.0 g, 52.9 mmol) in ethanol (200 mL), the solution of NH2OH-HCl (4.0 g, 58.2 mmmol) in H20 (4 mL) was added dropwise. The mixture was stirred vigorously at about 65 C and stood overnight. The analysis by TLC indicated the complete consumption of starting material. The solution was concentrated to remove the solvent. The residue was dissolved in DCM and washed with water, brine, dried over Na2S04 and concentrated in vacuum to afford 4-Fluoro-N-hydroxy-benzamidine as pale- yellow solid (BB8).

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, 4-Fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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Electric Literature of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS (1M in toluene, 17.7 mL, 17.7 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) solution of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol) and cyclobutanecarbonitrile (1.39 g, 17.1 mmol, 3 eq) in toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 5 h, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0?95:5) to afford 933 mg of the title compound as a yellow oil: ESI-MS: 237.0/239.0 [M+H]+; tR=4.27 min (System 1); TLC: Rf’0.30 (Hex/EtOAc, 9:1).

The chemical industry reduces the impact on the environment during synthesis Cyclobutanecarbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 326-62-5 name is 2-(2-Fluorophenyl)acetonitrile, 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. 326-62-5

General procedure: A solution of aryl acetonitrile 2 (50 mg), and triethylamine (1.1 equiv.) in dimethylformamide dimethyl acetal (0.5 mL, 3.76 mmol) was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT, and solvents were then evaporated. To the resulting crude product 3 was added hydrazine mono-hydrobromide (3.0 equiv.), 200 proof EtOH (1.0 mL), and H2O (0.3 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. The mixture was cooled to RT and concentrated in vacuo. The resulting residue was subjected to liquid-liquid extraction using saturated NaHCO3 (aq) and CH2Cl2. The organic layer was collected, dried over anhydrous MgSO4, filtered and removed under vacuum to afford 4.The resulting crude product 4 and 2-arylsubstitutedmalondialdehydes or 1,1,3,3tetramethoxypropane (1.0 equiv.) were dissolved in glacial AcOH (1.0 mL) and 200 proof EtOH (1.5 mL). The mixture was heated in a microwave reactor at 120 C for 20 minutes. After cooling on ice, the precipitate was collected on a fine scintered-glass frit and washed with icecold EtOH (2 x 1.0 mL). The resulting crystals 5-32 were dried and collected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Fluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Singleton, Justin D.; Dass, Reuben; Neubert, Nathaniel R.; Smith, Rachel M.; Webber, Zak; Hansen, Marc D.H.; Peterson, Matt A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
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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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C9H6N2

Step B 4-Cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl)piperidine A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (19 g, 78 mmol) and homophthalonitrile (8.6 g, 60 mmol) and cesium carbonate (79 g, 241 mmol) was stirred at 60 C. for 12 hours. The solution cooled to room temperature and diluted with 500 ml EtOAc and washed with saturated aqueous NaHSO4 and saturated aqueous NaCl. The solution was dried over Na2SO4, concentrated in vacuo, and purified by PCTLC (30% EtOAc in Hexane) to afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl) piperidine as a yellow/orange oil. 1H NMR (CDCl3): delta7.81-7.79 (d, 2H), 7.67-7.65 (m, 2H), 7.51-7.47 (m, 1H), 4.31 (br s, 2H), 3.26 (br s, 2H), 2.33-2.20 (m, 4H), 1.48 (s, 9H).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6319932; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-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 67515-59-7, category: nitriles-buliding-blocks

4-fluoro-3-(trifluoromethyl)benzonitrile (1 g; 5.29 mmol; 1 eq.) and (R)-(-)-2-methylpiperidine (3.1 rmL; 26.4 mmol; 5 eq.) in DMSO (10 mL) were heated at 1000C under nitrogen for 12h. The reaction mixture was then diluted in EtOAc, washed with water, NaHCO3 sat and NH4CI sat. The organic phase was dried over MgSO4, filtered and evaporated under vacuum to give a yellow oil, that was submitted to the next step without further purification. HPLC (Method A) Rt 5.65 min. LC/MS (Method B): 269.1 (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, 4-Fluoro-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts