Month: March 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. 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H5F3N2

General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) was stirred for 10 minutes and to it was added DCM (4 mL) followed by the different aniline 7-10, 53 (2.4mmol). The reaction mixture was cooled to 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over 10 minutes and the reaction was then stirred at r.t. o.n. The mixture was then diluted with DCM (20 mL), washed with brine (20 mL), the organic layer was dried over Na2SO4 and concentrated to dryness. Aniline 9 (4.9 mmol) was dissolved in 9 mL toluene. Thiophosgene (10.67 mmol) was added dropwise and the mixture was stirred at 75 C for five days. Obtained in99% yield as a brown wax

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:
Article; Bassetto, Marcella; Ferla, Salvatore; Pertusati, Fabrizio; Kandil, Sahar; Westwell, Andrew D.; Brancale, Andrea; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 230 – 243;,
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Adding a certain compound to certain chemical reactions, such as: 70484-01-4, name is 4-Bromophthalonitrile, 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 70484-01-4, Quality Control of 4-Bromophthalonitrile

A stirrer,thermometer,condenser,A 100 mL four-necked glass flask equipped with a glass stopper was purged with nitrogen,The open end of the condenser was sealed with a gentle stream of nitrogen. Palladium acetate (1.1 mg, 0.005 mmol),2-dicyclohexylphosphino-2 ‘, 6’-dimethoxybiphenyl (4.1 mg, 0.01 mmol),4-bromophthalonitrile (104 mg, 0.5 mmol),4,4,5,5-tetramethyl-2- [p- (1,1,1,3,5,5,5-heptamethyltrisiloxane-3-yl) phenyl] -1,3- – borolane (255 mg, 0.6 mmol),And 1,4-dioxane (2 mL) were charged in a flask,The solid was dissolved by stirring at room temperature for 30 minutes. Cesium carbonate (326 mg, 1.0 mmol)Was added and the mixture was stirred at 25-29 C. for 12 days. Production of the target compound was confirmed by GC-MS of the reaction mixture.5 mL of toluene and 5 mL of water were added in order to the reaction mixture, and the mixture was stirred at room temperature for 5 minutes, then separated, and the organic layer was concentrated under reduced pressure.The residue was dissolved in toluene, filtered through 10 g of activated alumina, and the obtained crude product was purified by preparative GPC to obtain 142 mg of the objective compound as a white solid.

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; SHIN-ETSU CHEMICAL COMPANY LIMITED; KIYOMORI, AYUMU; ITOH, YUSUKE; (49 pag.)JP2015/10084; (2015); A;,
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Reference of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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: In a 250 mL RBF, 3-aminobut-2-enenitrile (2.0 g, 0.24 mole) was added to a stirred solution of cyclohexyl hydrazine hydrochloride (4.0 g, 0.026 mole) and acetic acid (0.1 mL) in ethanol (60 mL). The reaction was refluxed for 6 h. Crude was evaporated and loaded on column to elute out product at 40% ethyl acetate in hexane. (1.74 g, 40%)

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

Reference:
Article; Sharma, Swagat; Kozek, Krystian A.; Abney, Kristopher K.; Kumar, Sushil; Gautam, Nagsen; Alnouti, Yazen; David Weaver; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 791 – 796;,
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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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6F3N

To a suspension of NaH (8.18 g, 135.13 mmol, 60%) in dimethyl sulfoxide (100 mL) were added dropwise a mixture of (4-trifluoromethyl-phenyl)-acetonitrile (236) (25 g, 135.13 mmol) and 1,4-dibromobutane (16 mL, 135.13 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (300 mL) at 0 C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water (100 mL) and 10% HCl solution (50 mL) were added to the mixture and extracted with ethyl acetate (2¡Á400 ml). The organic layer was dried over Na2SO4, concentrated and purified by 100-200 silica column chromatography using hexane as the eluent to give 1-(4-trifluoromethyl-phenyl)-cyclopentanecarbonitrile (237) (21 g, 65%) as a colorless liquid. [0908] GC-MS: 239 (M/H).

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 2338-75-2.

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); A1;,
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Application of 2920-38-9, 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. 2920-38-9, name is [1,1′-Biphenyl]-4-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

The synthetic route of [1,1′-Biphenyl]-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Yajun; Jin, Weiwei; Liu, Chenjiang; Molecules; vol. 24; 21; (2019);,
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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. 35747-58-1, name is 5-Amino-2-chlorobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5ClN2

Reference Example 9b 2-chloro-5-piperazin-1-yl benzonitrile 3-Cyano-4-chloroaniline (10.1 g, 66 mmol), as prepared in Reference Example 9a, was dissolved in n-butanol (300 mL) bis-(2-chloroethyl)amine hydrochloride (23.2 g, 130 mmol) and potassium iodide (50 mg, catalytic) were added. The mixture was heated at reflux for three days, then cooled in a refrigerator overnight. A solid precipitate was collected by filtration, washed with cold n-butanol and dried. The crude product was distributed between methylene chloride and 2N ammonium hydroxide. The organic layer was separated, dried (Na2SO4) and concentrated to yield a light yellow solid (9.1 g, 59%) which gave a single peak by GC and TLC analysis.

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; Pierson, Edward; Sohn, Daniel; Haeberlein, Markus; Davenport, Timothy; Chapdelaine, Marc; Horchler, Carey; McCauley, John P.; US2003/13708; (2003); A1;,
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Related Products of 70484-01-4, 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. 70484-01-4, name is 4-Bromophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound B-3 (8.4 mmol) and Compound E-4 (2.8 mmol) were reacted in the presence of DBU (11.2 mmol)And reacted under n-pentanol reflux conditions to obtain compound F-1 (0.28 mmol, 10%).To compound F-1 (0.28 mmol) in DMF,Zinc acetate was added and the mixture was stirred at 80 C. for 2 hours to obtain F-2 (0.25 mmol, 90%).F-2 (0.25 mmol) was dissolved in dichlorobis (triphenylphosphine) palladium (II) (PdCl 2 (PPh 3) 2)After cross coupling with triisopropylsilylacetylene in the presence of copper iodide,Treated with tetra-n-butylammonium fluoride (TBAF)Compound F-3 (0.19 mmol, 76%) was obtained.Compound F-3 (0.19 mmol) was cross-coupled with 4-iodobenzoic acid to obtain phthalocyanine dye D-2 (0.11 mmol, 58%).

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

Reference:
Patent; NIPPON STEEL & SUMIKIN CHEMICAL COMPANY LIMITED; KYUSHU INSTITUTE OF TECHNOLOGY; HAYASE, SHUZI; PANDEY, SHYAM SUDHIR; YAMAGUCHI, YOSHIHIRO; OCHI, NORIAKI; FUJINO, KENICHI; OKAMOTO, ETSUYA; KOMAYA, YOHEI; (25 pag.)JP5906522; (2016); B2;,
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Some common heterocyclic compound, 64829-31-8, name is 3-Methoxy-4-methylphenylacetonitrile, molecular formula is C10H11NO, 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: C10H11NO

A 40 mL scintillation vial was charged with compound 79 (250 mg, 1.55 mmol), NBS (331 mg, 1.86 mmol), AIBN (50.9 mg, 0.31 mmol) and CCl4 (5 mL). The reaction mixture was stirred at 70 C. for 2 h. After cooling, the reaction mixture was evaporated to dryness. Flash chromatography (24 g column, 0 to 40% EtOAc in hexanes) gave compound 80 (189 mg, 0.787 mmol, 51% yield) as a solid. LC-MS (ES, m/z): No ion detected. 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=7.7 Hz, 1H), 6.88 (d, J=7.7 Hz, 1H), 6.84 (s, 1H), 4.53 (s, 2H), 3.92 (s, 3H), 3.74 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64829-31-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; HE, Liqi; SIVAPRAKASAM, Prasanna; BROEKEMA, Matthias; COX, Matthew; TARBY, Christine M.; ZHANG, Qian; (75 pag.)US2020/38403; (2020); A1;,
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Application of 17626-40-3,Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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: 1H-benzo[d]imidazole-5-carbonitrile3, 4-Diaminobenzonitrile (1.0 g; 7.5 mmol) was dissolved in formic acid (3 ml_) and heated at 100C for 1.5 hours. The mixture was cooled, neutralised with 10% sodium hydroxide and the resulting precipitate isolated by filtration and dried in vacuo to yield the title compound as a brown solid (890 mg; 82%). 1H NMR (DMSO-de) delta 8.50 (1 H, s), 8.19 (1 H, s), 7.79 (1 H, d, J= 8.3 Hz), 7.62 (1 H, dd, J = 8.3, 1.54 Hz). LC/MS (Method C): 144 (M+H) HPLC (Method F) Rt = 2.14 min (Purity: 99.4%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Diaminobenzonitrile, its application will become more common.

Reference:
Patent; MERCK SERONO S.A.; WO2009/80663; (2009); A1;,
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Electric Literature of 17417-09-3, 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 17417-09-3 as follows.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), triazole (228.7 mg, 3.31 mmol) and K2CO3 (832.0 mg, 6.02 mmol) were added to THF (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with ethyl acetate (30 mL*3). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid. The crude solid was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100:0 to 50:50) to afford 5-nitro-2-(1H-1,2,3-triazol-1-yl)benzonitrile, 11a (500 mg, 77.2%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.74 (d, J=2.6 Hz, 1H), 8.65 (dd, J=2.4, 9.0 Hz, 1H), 8.48 (d, J=0.9 Hz, 1H), 8.27 (d, J=9.0 Hz, 1H), 7.98 (d, J=0.9 Hz, 1H).

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
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