Month: March 2021

Application of 712-74-3, These common heterocyclic compound, 712-74-3, name is Benzene-1,2,4,5-tetracarbonitrile, 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.

Cocrystal IV. Equimolar(0.1 mmol) ANPO and TCNB were stirredand dissolved in 16 mL acetonitrile/dichloromethane (1:1) mixed solventswithin a ventilated glass flask. Evaporating for one week at ambient temperature, the mother liquid separated out orange rod-like crystals (Scheme 2).

Statistics shows that Benzene-1,2,4,5-tetracarbonitrile is playing an increasingly important role. we look forward to future research findings about 712-74-3.

Reference:
Article; Sun, Hao; Khan, Arshad; Usman, Rabia; Wang, Mingliang; Journal of Photochemistry and Photobiology A: Chemistry; vol. 371; (2019); p. 315 – 326;,
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These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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. Formula: C14H10N2O2

To a mixture of 3-(2-aminoethyl)-1-(4-chlorobenzyl)-6-(3-fluoro-4-isopropoxyphenylimino)-1,3,5-triazinane -2,4-dion hydrochloride (200 mg, 0.413 mmol) and ethyl ether (8 mL) were added triethylamine (0.126 mL, 0.908 mmol) and diphenyl-N-cyanocarbonimidate (216 mg, 0.908 mmol), and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-6-(3-fluoro-4-isopropoxyphenylimino)-3-(4-cyanoimino-4-phenoxy-3-aza butyl)-1,3,5-triazinane-2,4-dion (170 mg, Yield: 70%) as colorless solid. 1H-NMR (delta ppm TMS/CDCl3): 1.40 (6H, d, J=6.0 Hz), 3.70 (2H, m), 4.07 (2H, m), 4.49 (1H, sept, J=6.0 Hz), 5.17 (2H, s), 6.47-6.61 (1H, m), 6.94 (1H, t, J=8.7 Hz), 7.16-7.20 (4H, m), 7.30-7.46 (4H, m), 7.79 (1H, m), 8.25 (1H, s).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; KAMEYAMA, Takayuki; HORIGUCHI, Tohru; ASAHI, Kentaro; ENDOH, Takeshi; FUJII, Yasuhiko; SHINTANI, Takuya; NAKAMURA, Ken’ichiroh; JIKIHARA, Sae; HASEGAWA, Tsuyoshi; OOHARA, Miho; TADA, Yukio; MAKI, Toshikatsu; IIDA, Akira; EP2604595; (2013); A1;,
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Application of 239087-12-8, These common heterocyclic compound, 239087-12-8, name is 3-Fluoro-5-(trifluoromethyl)phenylacetonitrile, 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.

Example S55; Preparation of 2-(3-fluoro-5-trifluoromethyl-phenyl)-ethylamine hydrochloride; 5.45 g of (3-fluoro-5-trifluoromethyl-phenyl)-acetonitrile (26.3 mmol) were dissolved in 45 ml THF and cooled down to 0 C. under nitrogen. 138 ml of a 1M borane-THF complex solution in THF (138 mmol) were then added dropwise over 20 min by keeping the temperature between 0-2 C. After addition the reaction mixture was stirred at rt for additional 45 min, and refluxed for 17 h. The reaction mixture was then cooled down to 0 C. and treated between 2 and 5 C. with 33 ml methanol over a period of 45 min. After 1 h refluxing the reaction mixture was concentrated, the residue dissolved in DCM and the amine extracted twice with 1N aqueous HCl. The combined aqueous phases are then treated with concentrated NaOH to adjust the pH to 12, and then extracted twice with DCM. The combined organic phases were then washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo leading to 4.44 g colorless oil. This was dissolved in 100 ml diethylether, treated with 9 ml 2.6N HCl in diethylether, stirred at rt for additional 30 min, filtered and dried under high vacuo, leading to 4.6 g white solid (72%). MS (ISP) 207.1 (M+H)+.

Statistics shows that 3-Fluoro-5-(trifluoromethyl)phenylacetonitrile is playing an increasingly important role. we look forward to future research findings about 239087-12-8.

Reference:
Patent; Conte-Mayweg, Aurelia; Kuehne, Holger; Luebbers, Thomas; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2006/30613; (2006); 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 613-46-7 as follows. category: nitriles-buliding-blocks

General procedure: A mixture of arylnitrile (2.0 mmol) and WR (1.07 g, 2.0 mmol) in 20 mL of dry toluene was refluxed for 8 h. Upon cooling to 90C 1.0 mL of water was added, the mixture was refluxed for another 1 h. After cooling to room temperature the reaction mixture was concentrated to ca. 5.0 mL and extracted with dichloromethane (20 mL x 3), the combined dichloromethane extracts were dried over MgSO4. The final residue was purified by silica gel chromatography (9 : 1 ethyl acetate /dichloromethane as eluent) to give the compounds 1a-1i.

According to the analysis of related databases, 613-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hua, Guoxiong; Du, Junyi; Slawin, Alexandra M. Z.; Woollins, J. Derek; Synlett; vol. 25; 15; (2014); p. 2189 – 2195;,
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Application of 34916-10-4,Some common heterocyclic compound, 34916-10-4, name is 4-Oxo-cyclohexanecarbonitrile, molecular formula is C7H9NO, 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.

Into a 250-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 119.1 (10 g, 81.20 mmol, 1.00 equiv), methanol (100 mL). This was followed by the addition of NaBH4 (1.52 g, 40.18 mmol, 0.50 equiv) at 0 C. in a water/ice bath. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 20 mL of NH4Cl (aq). The resulting solution was extracted with 2¡Á100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 10.02 g (99%) of 119.2 as colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Oxo-cyclohexanecarbonitrile, its application will become more common.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
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Synthetic Route of 179898-34-1, These common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-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.

Step 1 A solution of 3-bromo-5-fluorobenzonitrile (CIV) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CV) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

Statistics shows that 3-Bromo-5-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 179898-34-1.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); A1;,
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Application of 34403-48-0, A common heterocyclic compound, 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, molecular formula is C9H10N2, 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 solution of 4-(methylaminomethyl)benzonitrile (5.0 g, 1 eq.) and triethylamine (8.65g, 2.5 eq.) in dichloromethane (100 ml.) was added 2,2,2-trifluoroethanesulfonyl chloride (0520) (7.49 g, 1 .2 eq.). The mixture was stirred at room temperature for two hours. Then ethyl acetate was added, the organic layer was washed with water, dried over sodium sulfate and (0521) concentrated in vacuo to yield the title compound (10.4g) as yellow solid witch was used without further purification

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; TERTERYAN-SEISER, Violeta; GRAMMENOS, Wassilios; QUINTERO PALOMAR, Maria Angelica; CRAIG, Ian Robert; WIEBE, Christine; MENTZEL, Tobias; FEHR, Marcus; ESCRIBANO CUESTA, Ana; WINTER, Christian Harald; LOHMANN, Jan Klaas; MUELLER, Bernd; GROTE, Thomas; CAMBEIS, Erica; (62 pag.)WO2018/114393; (2018); 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 1009-35-4 as follows. Quality Control of 4-Fluoro-3-nitrobenzonitrile

10623] To a stirred solution of 4-fluoro-3-nitrobenzonitrile (1 g, 6.02 mmol) in CH2C12 (5 mE) was added potassium carbonate (1.66 g, 12.05 mmol) followed by cyclopropanamine (3.33 mE, 48.19 mmol) dropwise at 0¡ã C. under an inert atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 4 h. After consumption of starting material (by TEC), the reaction mixture was poured into water (30 mE) and extracted with EtOAc (2×50 mE). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 4-(cyclopropylamino)-3-ni- trobenzonitrile (1.1 g) as a yellow solid. The crude material was taken to the next step without further purification.10624] ?H NMR (400 MHz, CDC13): oe 8.49 (d, J=1.9 Hz,1H), 8.41 (brs, 1H), 7.66-7.63 (m, 1H), 7.40 (d, J=9.0 Hz,1H), 2.68-2.61 (m, 1H), 1.04-0.98 (m, 2H), 0.75-0.70 (m,2H)10625] EC-MS: m/z 202.0 [M?H] at 2.88 RT (99.48percent purity)

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Viamet Pharmaceuticals (NC), Inc.; Sparks, Steven; Yates, Christopher M.; Shaver, Sammy R.; Hoekstra, William J.; (156 pag.)US2018/185362; (2018); A1;,
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Related Products of 2338-76-3, 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. 2338-76-3, name is 3-(Trifluoromethyl)phenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(3-(trifluoromethyl)phenyl)acetonitrile (3.000 g, 16.203 mmol) and sodium hydride (60.00percent, 1.426 g, 35.647 mmol) in N,N-dimethylformamide (100 mL) at 0 ¡ãC, After the addition of 1,3-dibromopropane (1.731 mL, 16.203 mmol) this mixture was stirred at room temperature for 17 hours, a saturated aqueous solution of sodium bicarbonate (10 mL) was added to the reaction mixture at room temperature and the reaction was stirred for 10 minutes. The solvent was removed from the reaction mixture under reduced pressure, the obtained concentrate was poured into water and extracted with ethyl acetate. 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 = 0percent to 5percent) and concentrated to give the title compound (0.945 g, 25.9percent) as a colorless oil.

The synthetic route of 3-(Trifluoromethyl)phenylacetonitrile has been constantly updated, and we look forward to future research findings.

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;,
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Reference of 107-91-5, 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 107-91-5 as follows.

Add 13.8 g (0.1 mol) to a 250 mL three-necked bottlePotassium carbonate, dissolved in 100 mL of water, added 11.0 g (0.1 mol)Acetylacetone, 8.4 g (0.1 mol) of cyanoacetamide was added in portions at room temperature.During the feeding process, the temperature slowly rises by about 10 C.A large amount of solid precipitated out as the reaction proceeded. After 24 h, the reaction was stopped by TLC (MeOH: DCM = 1: 20) and filtered.The filter cake was washed three times with water.Dry to give 14 g of a white solid.The solid was recrystallized from 1 L of methanol.13.0 g of a white needle-like solid was obtained in a yield of 87.8%.

According to the analysis of related databases, 107-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenyang Pharmaceutical University; Chen Guoliang; Wang Lihui; Zhou Qifan; Du Fangyu; Dong Xiaoyu; Yang Jingyu; Wu Chunfu; (48 pag.)CN109320499; (2019); A;,
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