Month: June 2021

Electric Literature of 36282-26-5, 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 36282-26-5 as follows.

A mixture of 4-fluoro-2-bromobenzonitrile (10.0 g, 50.0 mmol), potassium acetate (9.82 g, 100 MMOL), bis (pinacolato) diboron (14.0 g, 55.0 mmol) and dichloro [L, L’-BIS (diphenylphosphino) FERROCENE] PALLADIUM (II) CH2CL2 adduct (0.82 g, 1.0 mmol) in 1,4-dioxane (150 ml) and dimethylsulfoxide (3 ml) was degassed with nitrogen for 1 h then heated at 85C for 20 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. The residue was stirred with 2 N sodium hydroxide (250 ml) for 10 min then filtered. The filtrate was extracted with diethyl ether (300 ml) and the organics discarded. The aqueous component was cooled to 0C then treated with 5 N hydrochloric acid, added dropwise over 15 min until the pH was 8. The aqueous phase was extracted with EtOAc (2 x 200 ML), THE COMBINED organics were dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (10.9 g, 88%) as a pale brown solid: BA (360 MHz, CDCL3) 1.38 (12 H, s), 7.15-7. 25 (1 H, M), 7.53-7. 60 (1 H, m), 7.67-7. 75 (1 H, m).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Safety of 4-Bromo-2-methylbenzonitrile

To a solution of 4-bromo-2-methylbenzonitrile (2.0 g, 10.2 mmol) in THF (100 ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5 M solution of n-butyl lithium (4.48 ml, 11.2 mmol). The mixture was stirred at -78C for 1h and then poured onto solid carbon dioxide (5 g) in THF (50 ml). The mixture was allowed to warm to room temperature. Water was added (200 ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HCl and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgSO4, and concentrated in vacuo to give a white solid identified as 4-cyano-3-methylbenzoic acid (1.2 g, 73%).

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; Ferring B.V.; EP1449844; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 34916-10-4, These common heterocyclic compound, 34916-10-4, name is 4-Oxo-cyclohexanecarbonitrile, 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.

Step A: [1-(4-Cyano-cyclohexyl)-azetidin-3-yl]-carbamic acid tent-butyl ester To a solution of 4-oxo-cyclohexanecarbonitrile (2.66 g, 21.5 mmol, prepared according to the procedure from Tremblay, Maxime, PCT Int. Appl. (2007), WO 2007013848) and azetidine-3-yl-carbonic acid tert-butyl ester (Beta Pharma, 3.70 g, 21.5 mmol) in DCM (20 mL) was added NaBH(OAc)3 (Aldrich, 6.84 g, 32.25 mmol). The resulting mixture was stirred at rt for 6 h and quenched with saturated NaHCO3. Workup and purification by column chromatograph (eluent: 80% EtOAc in hexanes to EtOAc only) gave the product as a mixture of cis/trans isomers. LC/MS: 280.2 [M+H].

The synthetic route of 34916-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Xuqing; Hufnagel, Heather Rae; Cai, Chaozhong; Lanter, James C.; Markotan, Thomas P.; Sui, Zhihua; US2010/267688; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 22364-68-7,Some common heterocyclic compound, 22364-68-7, name is 2-(o-Tolyl)acetonitrile, molecular formula is C9H9N, 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.

1-(2-Methylphenyl)acetonitrile (610 mg) was dissolved in dimethyl sulfoxide (6.1 ml), added with sodium hydride (60%, in oil, 409 mg) and stirred at room temperature for 30 minutes. This reaction mixture was added with the solution of bis(2-chloroethyl)benzylamine (1.090 g) dissolved in dimethyl sulfoxide (6.1 ml) obtained above and further stirred at 75 C. for 2.5 hours. The reaction mixture was added with water (50 ml) and extracted twice with ether (50 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=6:1) to obtain 1.077 g of the title compound. Yield: 80%. 1H-NMR (CDCl3) delta (ppm); 2.07 (2H, td, J=12 Hz, 3 Hz), 2.32 (2H, dd, J=12 Hz, 3 Hz), 2.59 (2H, t, J=12 Hz), 2.64 (3H, s), 3.01 (2H, d, J=12 Hz), 3.61 (2H, s), 7.20-7.40 (9H, m) MS (TSP); m/z 291 (MH+)

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

Reference:
Patent; Tsushima, Masaki; Tadauchi, Kaori; Asai, Kenji; Miike, Naoko; Imai, Masako; Kudo, Toshiaki; US2003/171370; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1897-52-5, name is 2,6-Difluorobenzonitrile, 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 1897-52-5, Recommanded Product: 2,6-Difluorobenzonitrile

58. Preparation of 3-Amino-4-fluoro-1-methylindazole Methylhydrazine (4.96 g, 108mmol was added to a solution of 15.0 g (108 mmol) of 2,6-difluorobenzonitrile in 150 mL of ethanol and the mixture was heated to reflux with stirring for 72 hours. The volatiles were then removed by evaporation under reduced pressure and the residue was dissolved in dichloromethane. The resulting solution was washed with water, dried over magnesium sulfate, and evaporated to dryness under reduced pressure to obtain the title compound as a white solid. This was recrystallized from ethanol to obtain 10.1 g (57 percent of theory) of the title compound as white crystals melting at 125-127 C. Elemental Analysis C8 H8 FN3 Calc.: %C, 58.2; %H, 4.88; %N, 25.4 Found: %C, 58.7; %H, 4.76; %N, 25.9 1 H NMR CDCl3: 7.19 (m, 1H), 7.11 (d, 1H, J=8.4), 6.59 (d of d, 1H, J=8.4, 3.3), 5.26 (brs, 2H), 3.72 (s, 3H); 13 C NMR CDCl3: 157.35, 154.88, 146.20, 146.18, 143.85, 143.76, 127.62, 127.55, 105.31, 105.27, 103.44, 103.24, 101.96, 101.78, 34.74.

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; DowElanco; US5571775; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A test tube equipped with a stopper was charged with 10 mg (0.029 m mol) of [(=T :)-4-] [4-dimethylamino-1- (4′-fluorophenyl)-1-hydroxybutyl]-3-hydroxymethylbenzonitrile, 10 mg of Novozym 435 (product of NOvozymes), 33 mg (0.29 [M MOL)] of vinyl butyrate and 1 ml of various kinds of solvents, and stirred at [30C] for 16 hours. After the reaction, converted ratios and optical purities were analyzed and E-values were calculated. The results are shown in Table 9.

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-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 147754-12-9, 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. 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-fluoro-2-methylbenzonitrile (2 g, 14.8 mmol), NBS (2.64 g, 15 mmol) and AIBN (100 mg) in CCl4 was refluxed under nitrogen for 2 hours. The reaction was cooled to room temperature. The solid was removed by filtration. The organic solution was concentrated to give crude product as an oil, which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): delta 7.68 (dd, J= 5.2, 8.4 Hz, 1H), 7.28 (dd, J= 2.4, 8.8 Hz, 1H), 7.12 (m, 1H), 4.6 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda San Diego, Inc.; EP1586571; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 71825-51-9,Some common heterocyclic compound, 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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.

2-methyl-2-(4-nitrophenyl) propanenitrile (4.5 g, 23.6 mmol) was added to a reaction vessel, to which were successively added Pd/C (450 mg) and 50 mL ethyl acetate. The system was vacuumed and hydrogen was introduced. The resulting mixture is reacted at room temperature for 15 hrs. The resulting reaction was filtered with Celite, and washed with ethyl acetate. The resulting filtrate was concentrated to obtain a colorless oil of 2-(4-aminophenyl)-2-methyl propanenitrile (3.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-2-(4-nitrophenyl)propanenitrile, its application will become more common.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; SHU, Chutian; EP2896622; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 3215-64-3 as follows. Computed Properties of C8H5Cl2N

2-(2,6-dichlorophenyl)acetonitrile (5.581 g, 29.999 mmol) in N,N-dimethylformamide (50 mL) at 0 C then sodium hydride (60.00%, 3.000 g, 74.997 mmol) was added and the mixture was stirred at the same temperature for 30 minutes. To this reaction mixture 1,3-dibromopropane (3.059 mL, 29.999 mmol) was added and further stirred at room temperature for 21 hours. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 0% to 50%) and concentrated to give the title compound (2.174 g, 32.0%) as a white solid.

According to the analysis of related databases, 3215-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products 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.

4-amino-3-nitrobenzonitrile (1.0 eq) was reacted with 2,5-dimethoxy- tetrahydrofuran (1.0 eq) in acetic acid. The reaction was heated in a microwave oven at 160ºC for 10 min. The solvent was evaporated and the residue purified by flash chromatography on silica gel (hexanes/EtOAc gradient). 3-nitro-4-(1H-pyrrol-1-yl)benzonitrile was obtained as an orange-yellow solid (59% yield). LCMS (ES): >;95% pure, m/z 214 [M+l]+.

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; CYLENE PHARMACEUTICALS, INC.; PIERRE, Fabrice; HADDACH, Mustapha; CHUA, Peter, C.; WO2010/135571; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts