Month: March 2021

Synthetic Route of 21667-62-9,Some common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, molecular formula is C9H6ClNO, 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 stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0 C. under nitrogen atmosphere. The mixture was warmed to 25 C. and then heated at 60 C. for 3 hours. After cooling to 0 C., a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-1-(3-chloro-phenyl)-propan-1-ol obtained was used in the next step without further purification. (Yield 14.5 g, crude). LC-MS: [M+H]+ 186.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(3-Chlorophenyl)-3-oxopropanenitrile, its application will become more common.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 10412-93-8, name is N-Benzyl-2-cyanoacetamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H10N2O

General procedure: N-benzyl-2-cyanoacetamide (1) was synthesized from benzylamineand ethyl cyanoacetate following the reported procedure[30] (Table 1).A mixture of N-benzyl-2-cyanoacetamide (1 mmol),aromatic aldehydes (1 mmol), 2-naphthol (1 mmol)and piperidine (0.1 mmol) in absolute EtOH (5 ml) wasrefluxed for an appropriate time as shown in Table 2. The reaction progress was monitored by TLC. After completionof the reaction, the mixture was cooled to r.t and thenH2O(5 mL) was added. The solid product was filtered,washed with cold distilled water (2 mL) to obtain essentiallypure products. The solid products were recrystallizedfrom ethanol.The structure of the products was characterized by IR, 1Hand 13C NMR spectra along with elemental analysis data.

According to the analysis of related databases, 10412-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pouramiri, Behjat; Tavakolinejad Kermani, Esmat; Khaleghi, Moj; Journal of the Iranian Chemical Society; vol. 14; 11; (2017); p. 2331 – 2337;,
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Nitriles – Chemistry LibreTexts

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. 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9NO

General procedure: To a stirring suspension of KOtBu (2.0 mmol) in 1,4-dioxane (5 mL) at 0C, corresponding (het)arylacetonitrile (1a-f, 10a-c) (1.0 mmol) in 1,4-dioxane (2 mL) was added dropwise. After further stirring for 10 minutes, a solution of respective Dithioester (2a-i) (1.0 mmol) in 1,4-dioxane (2 mL) was added to the reaction mixture at 0C, followed by further stirring for 1 h at ambient temperature (monitored by TLC). Iodine (506 mg, 2.0 mmol) was added and the reaction mixture was heated at 90C with continuous stirring (monitored by TLC). It was then diluted with 10% aq. Na2S2O3 solution (50 mL) and extracted with EtOAc (3×25 mL), and the combined organic layer was washed with water (3×25 mL) and brine (1×25 mL), dried (anhyd. Na2SO4), and concentrated under reduced pressure. The crude products were purified by silica gel column chromatography using EtOAc/hexane as eluent.

The synthetic route of 19924-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bonagiri, Saraiah; Acharya, Anand; Pasha, Mohamed A.; Hiriyakkanavar, Ila; Tetrahedron Letters; vol. 58; 49; (2017); p. 4577 – 4582;,
Nitrile – Wikipedia,
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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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6N2

General procedure: A mixture of 6-aryl-2-oxo-4-sec-amino-1-yl-2H-pyran-3-carbonitrile (0.5 mmol), 2-cyanomethylbenzonitrile (0.5mmol, 71.0 mg), and NaNH2 (1.0 mmol, 39.0 mg) in dryDMF (4.0 mL) was stirred at 100 C for 35-50 h. Aftercompletion of reaction, the mixture was poured onto crushedice followed by neutralization with 10% HCl. The solidmaterial formed was filtered, washed with water, dried, andpurified by silica gel column chromatography using hexane-EtOAc (7:3) as eluent.

According to the analysis of related databases, 3759-28-2, the application of this compound in the production field has become more and more popular.

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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Related Products of 64248-64-2, The chemical industry reduces the impact on the environment during synthesis 64248-64-2, name is 2,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

(i) Preparation of 2-(3-trifluoromethylphenoxy)-5-fluorobenzonitrile To a solution of 3-trifluoromethylphenol (29 g, 0.18 mol) dissolved in dimethylformamide (100 ml) was added finely-powdered potassium hydroxide (15 g, 0.19 mol). The reaction mixture was heated to approximately 60 C., with stirring, for one hour after which time 2,5-difluorobenzonitrile (25 g, 0.19 mol) was added and the temperature increased to 110 C. After approximately half an hour, the reaction mixture was allowed to cool and excess dimethylformamide was removed in vacuo before 500 ml of a 50:50 mixture of water and trichloromethane was added. The organic layer was separated, washed and dried and the residue purified by chromatography using a silica column with trichloromethane as eluant, followed by distillation and recrystallisation to yield the title compound as a solid. Melting point: 51 C. Analysis (%) Calc. C: 59.8; H: 2.5; N: 5.0 Found C: 59.8; H: 2.7; N: 5.2

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

Reference:
Patent; Shell Research Limited; US5304532; (1994); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H12N2

A mixture of 2-(4-amino-phenyl)-2-methyl-propionitrile (160 mg; 0.50 mmol), prepared as in l(B), 2-chloro-4,5-dimethoxy-benzoic acid (108 mg, 0.50 mmol), HOBt (77.0 mg; 0.50 mmol), EDC (144 mg; 0.75 mmol) and TEA (140 uL; 1.00 mmol) in dioxane (6 mL) was warmed at 100C for 2 hours. Then, the reaction was diluted with DCM and washed with IN HCl and 5% NaHCO3. The organic phase was collected, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by chromatography [SiO2, Petroleum ether/EtOAc (1/1)] to give the title compound as a white solid (30.0 mg; 17% yield).IH NMR (300 MHz, CDC13-d) delta(ppm): 8.33 (br. s., 1 H), 7.70 (m, 2 H), 7.50 (m, 2 H), 7.48 (s, 1 H), 6.91 (s, 1 H), 3.94-3.97 (m, 3 H), 3.95 (d, 3 H), 1.76 (s, 6 H).LCMS (RT): 2.24 min (Method G); MS (ES+) gave m/z: 359.18 (MH+). MP: 142-144 C.

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 115279-57-7.

Reference:
Patent; ADDEX PHARMA SA; WO2008/117175; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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. name: 2-Bromo-4-fluorobenzonitrile

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) in ether (100 mL) was added MeMgBr (25 mL, 75 mmol) at room temperature. The solution was stirred at room temperature for 0.5 hour before Ti(Oi-Pr)4 (41 mL, 25 mmol) was added and the resulting mixture was heated to reflux for 6 hours. Aqueous NaOH (10%, 200 mL) solution was then slowly added to the reaction mixture at 0 C and the reaction mixture was stirred at room temperature for additional 30 minutes. After dilution with aq. Na2C03 (5%, 400 mL) solution, it was extracted with t-BuOMe (100 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue obtained was diluted with aq. HC1 solution (5%) and the aqueous layer was washed with t-BuOMe (50 mL x 2) and basified with 20% aq. NaOH to pH~ 10. The resulting aqueous layer was further extracted with t-BuOMe (100 mL x 3). The combined organic layers were then dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography to give the title product (3.0 g, yield 51.7%) as yellowish oil. MS: 231.7 (M+H+, IBr)

The synthetic route of 2-Bromo-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
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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. 4110-35-4, name is 3,5-Dinitrobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3,5-Dinitrobenzonitrile

3,5-Dinitrobenzonitrile(1.50 g, 7.77 mmol) was added to a slurry of pyridin-3-ol (739 mg, 7.77 mmol) and potassium carbonate (10.7 g, 77.7 mmol) in DMF (15 mL), the mixture was warmed to 60 C and stirred overnight. After cooling to RT the reaction was diluted with ethyl acetate (50 mL) and water (100 mL). The organic phase was separated, washed with saturated sodium bicarbonate (50 mL) and brine (50 mL), dried ( a2S04), concentrated in vacuo and purified by chromatography (Si-40 column, ethyl acetate/hexanes) to give a light yellow solid identified as 3-nitro-5- (pyridin-3-yloxy)benzonitrile (1.31 g , 69% yield). MS (ESI) m/z: 242.0 (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; DECIPHERA PHARMACEUTICALS, LLC; FLYNN, Daniel L.; PETILLO, Peter A.; KAUFMAN, Michael D.; WO2013/36232; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 25808-30-4, 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The amino-nitrile (1 mmol) is dissolved in dry CH2Cl2 (5 mL) to which is added benzene (2 mL). With stirring, triflic acid (2 mL) is then slowly added and the reaction mixture is stirred overnight at 60-80 ¡ãC. The mixture is then quenched by pouring the solution over ice/water. The aqueous solution is then made basic by slow addition of 10 M NaOH and the solution is extracted twice with chloroform. The organic layer is washed with water, brine (2.x.20 mL) and dried over anhydrous sodium sulfate. In the event that imine/ketone mixtures are obtained, it may be necessary to stir the triflic acid/ice/water mixture for few hours in order to ensure complete hydrolysis. The products are purified via column chromatography (silica gel; hexanes/ether).

The chemical industry reduces the impact on the environment during synthesis 2-(Methylamino)acetonitrile hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Raja, Erum K.; Klumpp, Douglas A.; Tetrahedron; vol. 67; 25; (2011); p. 4494 – 4497;,
Nitrile – Wikipedia,
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Application of 6393-40-4, 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. 6393-40-4 name is 4-Amino-3-nitrobenzonitrile, 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.

Step 1 3,4-Diaminobenzonitrile 2-Nitro-4-cyanoaniline (2.21 g) was hydrogenated using 7.5% palladium carbon (320 mg) in ethanol (44 ml) at atmospheric pressure over 2 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. To the obtained residue was added chloroform and the resultant solid was collected by filtration and dried under reduced pressure to give the title compound (474 mg). 1H-NMR (delta ppm, DMSO-d6) 4.82-4.85 (2H), 5.41-5.43 (2H), 6.54 (d, J=8.1 Hz, 1H), 6.75 (d, J=2.1 Hz, 1H), 6.79 (dd, J=2.1, 8.1 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts