Tag: M.W=100-200

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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5414-21-1

General procedure: A stainless steel autoclave was charged with glycerol (1 mmol), base B (6 mmol), and NMP (1mL), flushed three times with CO2, and finally charged with CO2 to 0.7 MPa at room temperature.The obtained mixture was magnetically stirred at 25 C for 1 h, and an alkyl halide (10 mmol) wasadded at room temperature after CO2 evacuation, followed by repeated CO2 flushing/charging to 0.7MPa. The reaction mixture was magnetically stirred at 25 C for 18 h under 0.7 MPa pressure ofCO2. After EtOAc was added to the resulting mixture to precipitate the dissolved salt, the salt wasremoved using a Buchner funnel and washed with EtOAc. The combined filtrate was concentrated in vacuo, and the obtained product ratios were determined by 1H NMR measurements. The crudeproduct was purified by silica gel column chromatography, affording linear tricarbonates 1.Compounds 1g, 1h, and 1k were further purified by gel permeation liquid chromatography.

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; Mihara, Masatoshi; Moroga, Kaname; Iwasawa, Tetsuo; Nakai, Takeo; Ito, Takatoshi; Ohno, Toshinobu; Mizuno, Takumi; Synlett; vol. 29; 13; (2018); p. 1759 – 1764;,
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Electric Literature of 447-60-9,Some common heterocyclic compound, 447-60-9, name is 2-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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.

45.3 ml of a 1.8 M lithium diisopropylamide THF solution (81.6 mmol) was diluted with 68 ml of THF. Thereafter, 28 ml of a THF solution containing 5.0 g (27.2 mmol) of the 5-chloro-2,N-dimethylbenzamide prepared in Step A was added dropwise to the diluted solution at -78C. Thereafter, 28 ml of a THF solution containing 4.65 g (27.2 mmol) of 2-trifluoromethylbenzonitrile was further added thereto, and the obtained mixture was then stirred at -78C for 2.5 hours. The temperature of the reaction solution was increased to a room temperature, and a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, a solid generated as a result of vacuum concentration was filtrated, so as to obtain 6.87 g (78%) of 7-chloro-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless solid. 1H-NMR (270MHz, CDCl3) delta (ppm): 6.49 (1H, s), 7.33-7.72 (5H, m), 7.81-7.84 (1H, d, J=7.26Hz), 8.32-8.33 (1H, d, J=1.65Hz), 9.18 (1H, brs) ESI (LC-MS positive mode) m/z 324 (M+H).

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

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1724262; (2006); A1;,
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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. 119584-73-5, name is 2-Ethoxy-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8FNO

b) 4-Ethoxybenzo[d]isoxazol-3-amine I53 To a solution of acetohydroxamic acid (2.18 g, 29 mmol) in DMF (40 ml.) at 0 C under N2was added t-BuOK (3.26 g, 29 mmol) and the mixture was stirred at RT for 1 h. 2-Ethoxy-6-fluorobenzonitrile I52 (1.6 g, 9.7 mmol) was then added and the mixture was stirred at RT overnight. The mixture was diluted with DCM (80 ml_), washed with water (60 ml. x 4), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Pet.ether/EtOAc = 5/1) to give the title compound (240 mg, 15%) as a white solid. LCMS- E: Rt5.05 min; m/z 179.0 [M+H]+.

According to the analysis of related databases, 119584-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; MORROW, Benjamin, Joseph; FOITZIK, Richard, Charles; HEMLEY, Catherine, Fae; CAMERINO, Michelle, Ang; BOZIKIS, Ylva, Elisabet, Bergman; WALKER, Scott, Raymond; (321 pag.)WO2019/243491; (2019); A1;,
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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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 10406-25-4

Example 7 p-Cyanobenzylamine (13.2 g), water (18 g), and methylene chloride (18 g) were mixed, and the mixture was stirred with cooling with ice. Acetic acid (18 g) was added to the mixture. Subsequently, a 20 wt % aqueous solution (51.8 g) of sodium nitrite was added dropwise to the mixture over a one hour period. The mixture was stirred at the same temperature for four hours. The reaction mixture was subjected to extraction with methylene chloride, and the organic solvent was concentrated. Water was added to the concentrated solution, and the residual organic solvent was removed through distillation, to thereby obtain 14.7 g of p-cyanobenzyl acetate (yield 84%). The purity of the product was 98%.

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; Showa Denko K.K.; US6187945; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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 501-00-8, Quality Control of 2-(3-Fluorophenyl)acetonitrile

General procedure: To a solution of 11a-c (10 mmol) in anhydrous DMF (15 mL) was added appropriate aryl acetonitriles (12 mmol). After stirring at -10C for about 15 min, 60% NaH (0.48 g, 12 mmol) was added portion wise under a nitrogen atmosphere and maintained at this condition for 1 h. Then, the resulting mixture was warmed slowly to room temperature and continued to react for 12-24 h. After that, additional NaH (0.48 g, 12 mmol) was added and the air was introduced, the mixture was stirred at room temperature for another 12-24 h to yield 13a-q. Without further purification, 13a-q were hydrolyzed with 30% aqueous sodium hydroxide at room temperature for 4 h, and afterwards, the mixture was poured into 300 ml H2O and neutralized with 3N HCl. The precipitate was collected and purified by column chromatography on silica gel (hexane: EtOAc=8:1-1:1) to afford the target compounds 7a-q.

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:
Article; Wu, Hai-Qiu; Yan, Zi-Hong; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6477 – 6483;,
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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. 19472-74-3, name is 2-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromophenylacetonitrile

In a vial, 2-bromophenylacetonitirle (2 g, 10.2 mmol), m-tolylboronic acid (1.66 g, 12.2 mmol) and potassium carbonate (2.82 g, 20.4 mmol) were combined with toluene (15 ml), ethanol (15 ml) and water (5 ml) to give a light brown suspension. The mixture was degassed with argon and then tetrakis(triphenylphosphine)palladium(0) (354 mg, 306 mumol) was added. The reaction mixture was heated to 90 C. and stirred overnight. The resulting cooled mixture was diluted with water and extracted into EtOAc. The organic phase was separated and washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Chromatography (silica gel; 0% to 5% EtOAc in hexanes) provided the title product as a colourless oil (1.82 g; 80%). 1H NMR (300 MHz; CDCl3) delta ppm 2.42 (s, 3H), 3.65 (s, 2H), 7.03-7.62 (m, 8H).

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; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; F. HOFFMANN-LA ROCHE AG; BUSCHMANN, Helmut; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SMITH, Mark; SO, Sung-Sau; US2014/38990; (2014); A1;,
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Application of 64113-84-4, 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. 64113-84-4, name is 2-Fluoro-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Heat a solution of 2-fluoro-5-methyl-benzonitrile (2. [0G,] 14.80 mmol) with 4- chloro-2-nitro-phenylamine (2.5g, 14.80 mmol) and lithium hydroxide monohydrate (1.24g, 29.60 mmol) in DMSO (30 ml) to 55 [C] for 14 hours. Add an additional 0.61 g (14.80 mmol) of lithium hydroxide monohydrate, and increase heating to 70 [C,] continue for another 14 hours. Cool the reaction to ambient temperature and pour into a mixture of 100 ml water and 200 ml ethyl acetate. Extract with three 200 ml portions of ethyl acetate. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a step gradient starting with 90% hexanes: 10% ethyl acetate and going to 40% hexanes: 60% ethyl acetate to obtain 1.63 g [(5. 67] mmol, 38% yield) of the title compound as a red-orange amorphous solid: Mass Spectrum (m/e): 288 [(M+1).

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-Fluoro-5-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/14895; (2004); A1;,
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Synthetic Route of 6136-68-1, 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 6136-68-1 as follows.

Part A. Sodium methoxide (25% in MeOH, 1.5 mL, 6.8 mmol) was added dropwise to a solution of 3-acetylbenzonitrile (0.987 gm, 6.8 mmol) and 4-cyanobenzaldehyde (0.891 gm, 6.8 mmol) in dry methanol. Within 5 minutes, a precipitate began to form. The mixture was stirred at room temperature for 4 hrs and diluted with methanol. The solids were filtered off, washed with cold methanol and dried to give 3-[3-(4-cyanophenyl)-1-oxo-2-propenyl]benzonitrile as a white solid 1.7 gm (97%). MS:(M+H)+ 259; 1H NMR (CDCl3): 7.55 (d, 1H), 7.65 (t, 1H), 7.75 (s, 4H), 7.85 (m, 2H), 8.25 (d, 1H), 8.30 (s, 1H).

According to the analysis of related databases, 6136-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; EP892780; (2002); B1;,
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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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H5FN2

To a solution of 3-hydroxy-2,2-dimethyl-N-propy- lpropanamide (20.2 g, 0.127 mol) (Example 197d) in dry THF (500 mE) was carefully added NaH (60% in mineral oil, 7.64 g, 0.191 mol) in small portions at 0C. under nitrogen. The reaction mixture was then warmed to room temperature and stirred under nitrogen for 1 hr. To this solution was slowly added at room temperature 2-amino-6-fluorobenzo-nitrile (17.3 g, 0.127 mol) in THF (100 mE) and the reaction mixture refluxed overnight under nitrogen then cooled down to room temperature, quenched with brine, and extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2SO4, evaporated and the residue was crystallized from EtOAc/Hexane to give the compound as a white solid (16.5 g, 48%). MS 276 (MHj.

According to the analysis of related databases, 77326-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
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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. 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 147754-12-9

2-Bromomethyl-4-fluorobenzonitrile (32). 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 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; Feng, Jun; Gwaltney, Stephen L.; Stafford, Jeffrey A.; Zhang, Zhiyuan; Brodluahrer, Paul R.; Elder, Bruce; Isbester, Paul; Fornicola, Richard S.; Kisanga, Philip B.; Mobele, Bingidimi I.; Palmer, Grant J.; Reeve, Maxwell M.; Salsbury, Jonathon S.; Ulysse, Luckner; Venkatraman, Sripathy; US2009/275750; (2009); A1;,
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