Month: May 2021

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 191014-55-8 as follows. Recommanded Product: 4-Fluoro-2-methoxybenzonitrile

To a solution of 0.7 g of 1-[4-methyl-2-(4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propan-1-ol in 3 mL of dimethylformamide at 5 C. was added 113 mg of a 55% suspension of sodium hydride in mineral oil. The reaction mixture was stirred for 30 minutes at 5 C. The resulting mixture was slowly added to a solution of 429 mg of 4-fluoro-2-methoxy-benzonitrile in 1 mL of dimethylformamide at 5 C. The resulting mixture was stirred at 5 C. allowing the temperature to warm up to room temperature. It was then heated in a sealed tube to 60 C. under microwave irradiation for 15 minutes. After allowing it to cool down to room temperature, the mixture was poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 50/ethyl acetate 50) to give 1.05 g of 2-methoxy-4-{1-[4-methyl-2-(trans-1,4-trifluoromethyl-cyclohexyl)-oxazol-5-yl]-propoxy}-benzonitrile.C22H25F3N2O3 (422.45), MS (ESI): (M+H+) 423.4 (M+H+).

According to the analysis of related databases, 191014-55-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 143306-27-8, These common heterocyclic compound, 143306-27-8, name is 2-Fluoro-6-nitrobenzonitrile, 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.

Method AA Al 05 (500 mg), l-methyl-(4-methylamino)piperidine (440 muL) and Hnig base (600 muL) are suspended in 1.5 mL butanol and stirred for 1 h at 150 0C in a Biotage microwave. The reaction mixture is combined with water and DCM, the organic phase is separated off and dried.

The synthetic route of 143306-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/152014; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 10444-38-9,Some common heterocyclic compound, 10444-38-9, name is Ethyl 4-cyanobutanoate, molecular formula is C7H11NO2, 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: To a solution of the cyano ethyl esters (4.8mmol) in pyridine (26ml) were added water (13ml), acetic acid (13ml), sodium hyposphite (39.06mmol) and Raney nickel. The suspension was then stirred at 40C for 2hr. The catalyst was removed by filtration, and washed with ethanol (5ml). Water (300ml) and diethyl ether (80ml) were added to the filtrate, and the organic layer was separated. The aqueous phase was further extracted with diethyl ether (2x80ml), and the combined extracts were washed with water (300ml), and brine (100ml), and dried over Na2SO4 anhydrous, concentrated under vacuo, and the residue was purified by silica gel dry column vacuum chromatography ( DCVC) by stepwise gradient elution with dichloromethane/hexane (50:50 to 100:0).

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF SYDNEY; UNIVERSITY OF TECHNOLOGY SYDNEY; VANDENBERG, Robert; RYAN, Renae Monique; RAWLING, Tristan; IMLACH, Wendy; CHRISTIE, Macdonald; CARLAND, Jane; MOSTYN, Shannon; (169 pag.)WO2018/132876; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 42186-06-1, name is 2-(4-Bromophenyl)propanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-(4-Bromophenyl)propanenitrile

[00820] Example 42. Preparation of N-((6-(3-t°r^butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-l(2H)-yl)-2- methoxyphenyl)benzo[c/]isoxazol-3-yl)methyl)methanesulfonamide (compound IB-LO-2.45).; [00821] Part A. Preparation of N-((6-bromobenzo[(f]isoxazol-3-yl)methyl)-N-(4-methoxybenzyl)- methanesulfonamide.; [00822] To a refluxing solution of 6-bromo-3-methylbenzo[d]isoxazole (LOg, 4.72mmol) in CCl4 (25ml) was added l-bromopyrrolidine-2,5-dione (0.923g, 5.19mmol) and benzoic peroxyanhydride (0.114g, 0.472mmol). The mixture was refluxed for 6h, and then cooled to room temperature, filtered thru celite, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using CH2Cl2 as the eluent to give the dibromide as a solid (0.84g, 43%). To a solution of the dibromide (0.2Og, 0.687mmol) and N-(4-methoxybenzyl)methanesulfonamide (0.148g, 0.687mmol) in EtOH (3ml) was added IN aq. NaOH (0.722ml, 0.722mmol), and the resulting mixture was stirred at 8O0C for 90min. The mixture was partitioned between 0.1nu aq. HCL (1OmL) and EtOAc (2 x 1OmL), and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 2:3 EtOAc:hexanes as eluent to give the title compound as an oil (65mg, 22%).

The synthetic route of 42186-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/39134; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

(c) 4-Bromo-2-[[(1R)-3-chloro-1-phenylpropyl]oxy]-5-fluorobenzonitrile This was prepared by the method of Example 43(a) using 4-bromo-2,5-difluorobenzonitrile and (R)-alpha-(2-chloroethyl)benzenemethanol. 1H NMR 300 MHz (CDCl3) 8.02 (1H, s), 7.42-7.26 (5H, m), 7.06-7.03 (1H, m), 5.46-5.43 (1H, m), 3.82-3.62 (1H, m), 3.75-3.60 (1H, m), 2.75-2.5 (1H, m), 2.55-2.30 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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 66389-80-8, Product Details of 66389-80-8

Zn(OTf)2, 0.27g (2.5 mmol) of formamidine acetate, 58mg (0.25 mmol) nitrile ,0.20 mL DMF, and 0.40 mL (12.5 mmol) of anhydrous hydrazine was added. The vessel was sealed and the mixture was stirred in an oil bath at 30C for 36 hours. The reaction solution was cooled to room temperature and the seal was removed. Sodium nitrite (5.0 mmol, 345 mg) in 5 mL of water was slowly added to the solution and followed by slow addition of 1M HCl during which the solution turned bright red in color and gas evolved. Addition of 1M HCl continued until gas evolution ceased and the pH value is 3. (Caution: this step generates a large amount of toxic nitrogen oxide gasses and should be performed in a well ventilated fume hood). The mixture was extracted with EtOAc and the organic phase dried over sodium sulfate. The EtOAc was removed using rotary evaporation and the residue purified using silica column chromatography (Hexane:EtOAc=7: l) to give 50mg product as red solid, the yield is 70%. 1H NMR (500 MHz, CDC13) delta 1.49 (9H, s), 4.45 (2H, d, J = 5 Hz ), 4.97 (1H, bs), 7.53 (2H, d, J = 10 Hz), 8.60 (2H, d, J = 10 Hz), 10.21 (1H, s); 13C MR (125 MHz, CDC13) delta 39.07, 51.82, 118.84, 119.19, 120.76, 132.11, 141.12, 142.56, 149.36; HRMS [M+Na]+ m/z calcd. for [C9H16N502]+ 310.1276, found 310.1274.

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; DEVARAJ, Neal, K.; YANG, Jun; SECKUTE, Jolita; WO2013/152359; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 138642-47-4, 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. 138642-47-4 name is 2-Bromo-5-methoxybenzonitrile, 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.

General procedure: To a mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., Recommanded Product: 66389-80-8

c) N-Boc-4-aminomethyl-N-hydroxy-benzamidine; To a solution of N-Boc-4-aminoethylbenzonitrile (14g; 60mmol) in THF (500ml) is added at 50C a solution of hydroxy Ia mine in water (1/1 ; 80ml; 1.8 mol). The reaction mixture is then stirred at room temperature for 16 hours. The reaction mixture is diluted with water and THF is removed under vacuo. The resulting precipitate is collected by filtration and dried. Pure title compound is obtained by recrystallization from diethylether.

The synthetic route of 66389-80-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/37476; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 186517-05-5, name is 2,3-Difluoro-6-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H2F5N

Example 12 2-chloro-3-fluoro-6-trifluoromethylbenzonitrile (Compound No. 33) STR29 To a solution of 50.9 g of 2,3-difluoro-6-trifluoromethylbenzonitrile in 240 ml of dimethyl sulfoxide (DMSO) was added 53.3 g of calcium chloride and the mixture was stirred for 6 hours at a temperature of from 140 to 150 C. After cooling, the reaction mixture was further added with 240 ml water and extracted with 240 ml and 100 ml hexane twice. The organic layer obtained was dried over anhydrous magnesium sulfate, and the solvent therein was distilled under reduced pressure. The crude product obtained was distilled under reduced pressure to obtain 38.9 g of the title compound.

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 186517-05-5.

Reference:
Patent; Nippon Soda Co., Ltd.; US6054605; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 39186-58-8, name is 4-Bromo-2,2-diphenylbutyronitrile, 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 39186-58-8, SDS of cas: 39186-58-8

EXAMPLE 22 To 1.96 parts of piperidine is added 1.91 parts of potassium iodide and 25 parts deionized water under a nitrogen atmosphere. The mixture is gently warmed and 1.65 parts of potassium hydroxide and 7.51 parts of 2,2-diphenyl-4-bromobutyronitrile are added. The temperature is raised to reflux and maintained thereat for 4.5 hours. After cooling to room temperature, the reaction mixture is extracted three times with 14 part portions of ethyl ether. The ether extracts are combined, and extracted four times with 25 parts by volume portions of a dilute acetic acid solution. The acid extracts are combined, neutralized to about pH 10 with 50% sodium hydroxide solution, and extracted again with ethyl ether. The ether extracts are combined, washed twice with 50 parts by volume portions of a saturated sodium chloride solution, and dried over anhydrous potassium carbonate. The solvent is removed under reduced pressure to afford, as an off-white solid, in 86.1% yield, 2,2-diphenyl-4-piperidinobutyronitrile. This compound melts at 74 – 77 C., and is represented by the following structural formula. STR16

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-Bromo-2,2-diphenylbutyronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G. D. Searle & Co.; US4086234; (1978); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts