Month: July 2021

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. 16532-79-9, name is 4-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

To a solution of 4-bromophenyl acetonitrile (20 g, 102 mmol) in THF (20 mL) is added a solution of borane (1 M in THF, 300 mL) under a nitrogen atmosphere. The reaction mixture is stirred at 75 C overnight. It is cooled to room temperature and treated with 6 N HCl (500 mL) drop-wise and stirred further at room temperature for 5 h. The resulting mixture is washed with ethyl acetate and ethyl acetate is discarded. The aqueous layer is basified with sodium carbonate and then extracted with ethyl acetate several times. The combined organic layer is washed with water, dried (Na2SO4), and the solvent was removed under reduced pressure to obtain pale yellow oil without further purification (16 g, 78%).

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; NOVARTIS AG; WO2008/76954; (2008); A2;,
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 72035-46-2 as follows. Quality Control of 2,3-Bis(4-methoxyphenyl)propanenitrile

In the first step, formation of the substituted stilbene occurred through basic addition of 2-(4-methoxyphenyl)acetonitrile to 4-methoxybenzaldehyde in high yield. Reduction of the stilbene using NaBH4 to afford 2,3-bis(4-methoxyphenyl)propanenitrile was followed bytreatment with BBr3 to cleave the methyl ethers, giving DPN in high yield.DPN was then acetylated using acetic anhydride to provide Compound 1. Either the corresponding anhydride or acyl chloride was used to provide Compounds 2-6.For an exemplary synthesis of the R-enantiomer of DPN, see Carroll, VM. et al., J. Med. Chem. 2012 55:528-537.

According to the analysis of related databases, 72035-46-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; JUNG, Michael, E.; VOSKUHL, Rhonda, R.; (58 pag.)WO2018/49094; (2018); 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 64248-64-2 as follows. name: 2,5-Difluorobenzonitrile

To a solution of 1,1-dimethylethyl (35)-3-pyrrolidinylcarbamate (201 mg, 1.078 mmol) and 2,5-difluorobenzonitrile (150 mg, 1.078 mmol) in DMF (2.0 mL) was added K2CO3 (149 mg, 1.078 mmol). The reaction vial was capped and heated to 100 0C for 5 h. Upon cooling, water (5 mL) and EtOAc (2 mL) were added. The layers were separated, and the aqueous layer was extracted with EtOAc (4 x 2 mL). The combined organic layers were washed with brine (3 x 1 mL) and then concentrated onto Isolute. Purification via flash column chromatography (0-50% EtOAc/hexanes) afforded the title compound (143 mg, 43%). LC-MS m/z 306 (M+H)+, 1.09 min (ret time).

According to the analysis of related databases, 64248-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BULLION, Ann, Marie; BUSCH-PETERSEN, Jakob; EVANS, Brian; NEIPP, Christopher, E.; MCCLELAND, Brent, W.; NEVINS, Neysa; WALL, Michael, D.; WO2011/25799; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, molecular formula is C7H12N2O, 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. category: nitriles-buliding-blocks

Charge 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde 20g (0. 0947mole) of the formula 2 where R= ethyl and N, N-diethylamino cyanoacetamide of the formula (3) 14. 6g, (0.1042), acetic acid 3.13g and piperidine 4.45g along with toluene 200ml and heated to reflux temperature of about 100-115 C with continuous removal of water azeotrophically 15 hours. After the reaction is over the reaction mixture is concentrated to a volume of 20-30ml quenched in to dilute hydrochloric acid and chilled water 200ml and stirred for 60 minutes. The precipitated solid was filtered and dried to get 30g (95%), the HPLC purity is 94% (including isomer) of N, N-DIETHYL – 2-CYANO-3- (-3-ETHOXY-4-HYDROXY-5 NITROPHENYL) ACRYLAMIDE. The product is used as such directly to the. next stage. MR = 110.1- 117. 2 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26391-06-0, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LTD; JASTI, Venkat; WO2005/63693; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 134450-56-9, 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. 134450-56-9, name is 4,5-Difluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Type (1-1) synthetic method of compound structure shown in the: lower range of the nitrogen, the 4,5-difluoro -1,2-dicyanobenzene is hydrogenated (5mmol), phenoxazine (18mmol), Pd2(dba)3(0.8mmol), NaOtBu (30mmol) and tBu3P·HBF4(0.8mmol) into 100 ml dimethyl formamide in the DMF 80 C temperature under stirring overnight. The 10 ml in cold water is added to the mixture the reaction quenching. After cooling to room temperature to be mixture, by vacuum filtration, then through the column chromatography purification product type (1-1), the product is dried in a vacuum. Yield: 69%.

The chemical industry reduces the impact on the environment during synthesis 4,5-Difluorophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Photoelectric Co. Ltd. Kunshan States; duan, lian; zhang, yun ge; liu, song; Zhao, lei; (18 pag.)CN105418533; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 53312-81-5,Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

General procedure: A 150 mL four-necked flask with a magnetic stir bar was chargedwith compound 7 (3.24 g, 20 mmol), sodium bicarbonate (3.36 g,40 mmol, 2 equiv) and tetrahydrofuran (70 mL). At 45 C, a solutionof 3-bromo-4-fluoroaniline (4.18 g, 22 mol, 1.1 equiv) in tetrahydrofuran(15 mL)was added to the reaction mixture in 10 min. Thenthe reaction mixture was heat to reflux for another 3 h. Oncompleting of the reaction monitored by TLC, the sodium bicarbonatewas filtered and the filtrate was evaporated in vacuo. Theresidue was dissolved with ethyl acetate (70 mL), washed withwater (40 mL), brine, dried over anhydrous Na2SO4 and concentratedin vacuo. The crude product was slurried in petroleum ether(50 mL) for 1 h and the precipitate was collected by filtration anddried to give the desired product (5.75 g, 91%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Article; Du, Qianming; Feng, Xi; Wang, Yinuo; Xu, Xi; Zhang, Yan; Qu, Xinliang; Li, Zhiyu; Bian, Jinlei; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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. 143879-80-5, name is 2,3,4-Trifluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,3,4-Trifluorobenzonitrile

6,7-Difluoro-1H-inidazole-3-amine: [0237]; 0.32 cm3 of hydrazine monohydrate is added to 0.46 cm3 of 2,3,4-trifluorobenzonitrile in 10 cm3 of absolute ethanol. The medium is heated at about 75 C. for 17 hours, followed by addition of 10 cm3 of ethyl acetate, 5 cm3 of tetrahydrofuran and 5 cm3 of distilled water. The organic phase is separated out after settling the phases and is washed with 10 cm3 of distilled water and then with 10 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling the phases, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50 C.). The residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 mum; diameter 1.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume). The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa; 40 C.); after drying (90 Pa; 40 C.), 100 mg of 6,7-difluoro-1H-indazole-3-amine are obtained in the form of a white solid melting at 183 C. [0238] 1H NMR spectrum (300 MHz, (CD3)2SO d6, delta in ppm): 5.57 (unresolved complex: 2H); 6.93 (mt: 1H); 7.52 (ddd, J=8.5-4.5 and 1Hz: 1H); 12.01 (unresolved complex: 1H).

According to the analysis of related databases, 143879-80-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lesuisse, Dominique; Dutruc-Rosset, Gilles; Halley, Franck; Babin, Didier; Rooney, Thomas; Tiraboschi, Gilles; US2004/132794; (2004); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 67515-59-7, These common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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.

Reference Example 54 4-(3-formyl-2-methoxyphenoxy)-3-(trifluoromethyl)benzonitrile; [Show Image] To a solution (20 mL) of 3-hydroxy-2-methoxybenzaldehyde (1.00 g) in dimethyl sulfoxide were added lithium carbonate (743 mg) and 4-fluoro-3-(trifluoromethyl)benzonitrile (1.54 g), and the mixture was stirred at 100C for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropylether to give the title compound as a pale-yellow solid (yield: 1.50 g, 71%). 1H-NMR (DMSO-d6, 300 MHz):delta3.86 (3H, s), 7.01 (1H, d, J = 8.7 Hz), 7.40 (1H, dd, J = 8.1, 7.1 Hz), 7.62 (1H, dd, J = 8.1, 1.7 Hz), 7.74 (1H, dd, J = 7. 7, 1.7 Hz), 8.07 (1H, dd, J = 8.7, 2.1 Hz), 8.40 (1H, d, J = 2.1 Hz), 10.31 (1H, s).

Statistics shows that 4-Fluoro-3-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 67515-59-7.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2450352; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 127946-77-4, A common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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 H: (1R,2R)-2-(4-(4-bromophenyl)-2-(3,4-difluorophenyl)oxazol-5-yl)-N-(1-cyanocyclopropyl)cyclohexanecarboxamide [0231] To a solution of (1R,2R)-2-(4-(4-bromophenyl)-2-(3,4-difluorophenyl)oxazol-5-yl)cyclohexanecarboxylic acid (72 mg, 0.156 mmol) and HATU (89 mg, 0.389 mmol) in DMF (1 mL) was added 1-cyanocyclopropanaminium chloride (46.2 mg, 0.389 mmol) followed by the addition of Hunig’s base (101 mg, 0.779 mmol) and stirred at 40 C. overnight. The resulting solution was purified directly by reverse phase HPLC (Sunfire C18 30×150 mm column; 40 to 95% MeCN in water. 0.1% TFA modifier for MeCN and water) to give desired product as a white solid (32 mg, 39%).

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Stachel, Shawn; Paone, Daniel V.; Li, Jing; Nanda, Kausik; US2015/99719; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 clear amber solution of 2-trifluoromethyl 4-aminobenzonitrile (14.9 g; 80.8 mmol; 2.0 equiv) in 80 mL dry THF at 22C was added Compound IA (10.0 g; 40.4 mmol; 1.0 equiv), neat, by syringe. A slight exotherm was observed. The homogeneous amber solution stirred for 20 minutes, then placed in a 55C oil bath for 30 minutes. HPLC indicated only a small amount of aniline was present. The contents of the reactor were concentrated in vacuo, yielding a tan solid. After absorption onto silica, the crude material was purified by flash column chromatography (1% acetone/DCM to elute aniline, then 10-50% acetone/DCM to elute desired as a pale yellow band.) 20.3 g (94 %) of Compound IB was obtained as an off-white solid.[00153] 95% at 3.736 min (retention times) (YMC ODS-A column 4.6 x 50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% H3PO4, 4 mL/min, monitoring at 220 nm).

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/59077; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts