Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 21524-39-0, name is 2,3-Difluorobenzonitrile, 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 21524-39-0, SDS of cas: 21524-39-0

Method A (standard SNAr/CsF ) To a soln. of C-1 (1 eq) and BB-8 (1 to 1.1 eq) in DMSO (3 mL/mmol) was added CsF (2 eq). The rxn mixture was heated at a given temperature for a given time (see Table 26) and was partitioned between EtOAc and water. The org. phase was washed with water (3x) and with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc.

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; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (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. 85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, A new synthetic method of this compound is introduced below., Safety of N-(tert-Butoxycarbonyl)-2-aminoacetonitrile

General procedure: A 2-acylamidoacetonitrile was prepared similarly at room temperature, using an acid chloride as a starting compound. To a solution of the compound thus obtained (3 mmol) in dry methanol (50 mL) at room temperature under N2 atmosphere was added L-cysteine methyl ester hydrochloride (770 mg, 4.5 mmol) and triethylamine (0.63 mL, 4.5 mmol). The resulting mixture was stirred for 3 h and evaporated to dryness. The residue was taken up in CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic extract was dried over sodium sulfate, filtered, evaporated, and purified by column chromatography (silica gel, hexane/ethyl acetate, 5:1) to give a methyl ester of compounds 14 – 17. Precooled LiOH (0.9 mL, 1 N, 0.9 mmol) was added to the methyl ester (1.0 mmol) in methanol (5 mL) at 0 oC. The suspension was stirred for 1 h at room temperature, diluted with acetone (20 mL) to precipitate the product. The white powder was filtered and dried to give compounds 14 – 17.

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; Chen, Pinhong; Horton, Lori B.; Mikulski, Rose L.; Deng, Lisheng; Sundriyal, Sandeep; Palzkill, Timothy; Song, Yongcheng; Bioorganic and Medicinal Chemistry Letters; vol. 22; 19; (2012); p. 6229 – 6232;,
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Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)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 19924-43-7, Safety of 2-(3-Methoxyphenyl)acetonitrile

A mixture of (3-methoxyphenyl)acetonitrile (13.0 g, 88.0 mmol), O,O-diethyl dithiophosphate (14.9 mL, 97.0 mmol) and 4M hydrogen chloride-1,4-dioxane (177 mL, 707 mmol) was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (200 mL), water (200 mL) was added, and the organic layer was separated, washed successively with water (100 mL), 0.2N aqueous sodium hydroxide solution (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was treated with hexane (200 mL) in an ice bath to allow solidification. The solid was collected by filtration, and washed with hexane to give the title compound (12.6 g) as a white solid (yield 79%). 1H NMR (400 MHz, CDCl3) 5 3.81 (3H, s), 4.10 (2H, s), 6.49 (1H, brs), 6.80-6.81 (1H, m), 6.84-6.89 (2H, m), 7.31 (1H, t, J = 8.0 Hz), 7.46 (1H, brs).

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; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
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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. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,4-Difluorobenzonitrile

2-(Benzyloxy)-4-fluorobenzonitrile. Benzyl alcohol (13 mL, 125 mmol) was slowly added to a stirred suspension of NaH (95%, 2.86 g, 113 mmol) in toluene (200 mL) at room temperature. After 30 min, 2,4-difluorobenzonitrile (15.3 g, 110 mmol; Aldrich) was added all at once and stirring continued overnight (18 h). After this, the reaction mixture was washed with water (2 X 25 mL) and brine (25 ml). The organic layer was dried (Na2SO4), filtered and concentrated to give a white slurry which was triturated with hexanes and filtered to afford the title compound as a white solid (20.34 g, 81% yield). 1H NMR (500 MHz, CDCl3): 7.59-7.55 (IH, m), 7.45-7.34 (5H, m), 6.75-6.71 (2H, m), 5.19 (2H5 s); 13C NMR (125.76 MHz, DMSO-d6) delta ppm: 71.16, 98.75, 101.54, 101.75, 108.66, 108.84, 115.83, 127.16, 12.8.58, 128.94, 135.03, 135.44, 135.54, 162.22, 162.31, 165.26, 167.29. LCMS calcd for C14H11FNO: 228.2; found: 228.0.

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 3939-09-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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Reference of 160892-07-9, The chemical industry reduces the impact on the environment during synthesis 160892-07-9, name is 5-Bromoisophthalonitrile, I believe this compound will play a more active role in future production and life.

In a nitrogen atmosphere5-Bromoisophthalonitrile (30.0 g, 144.9 mmol)And (3,5-dichlorophenyl) boronic acid (30.4 g, 159.4 mmol)Were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed.After this, potassium carbonate (60.1 g, 434.7 mmol)In 180 ml of waterAfter thoroughly stirring, tetrakistriphenyl-phosphinopalladium (5.0 g, 4.4 mmol) was added thereto. After 8 hours of reaction, the temperature was lowered to room temperature and filtered.The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate.The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Compound 5A (30.5 g, 77%).

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

Reference:
Patent; LG CHEM, LTD.; JUNG, Min Woo; LEE, Dong Hoon; HUH, Jung oh; JANG, Boon jae; KANG, Min young; HEO, Dong Uk; HAN, Mi yeon; (26 pag.)KR2017/92131; (2017); A;,
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Application of 96606-37-0, The chemical industry reduces the impact on the environment during synthesis 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2,4,6-trifluorobenzonitrile (0.25g, 1.6mmol), potassium carbonate (0.99g, 7.2mmol), 2-phenylbenzimidazole (1.02g, 5.2mmol), DMSO 8ml , 150 heated to reflux 12h.Cooling to room temperature the precipitated solid was poured into 200ml of water was stirred 0.5h, filtered off with suction to give a white solid, purified by column chromatography to give a white solid 0.95g, 88% yield

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, 2,4,6-Trifluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Technology; TAO, YOU TIAN; WANG, FANG FANG; TANG, CHAO; HUANG, WEI; (6 pag.)CN104610162; (2016); B;,
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Application of 17417-09-3, 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. 17417-09-3 name is 2-Fluoro-5-nitrobenzonitrile, 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.

9.1. 2-(Dimethylamino)-5-nitrobenzonitrile: 1.66 g (10.0 mmol) of 2-fluoro-5-nitrobenzonitrile, 1.22 g (15.1 mmol) of dimethylamine hydrochloride and 3.46 g (25.1 mmol) of potassium bicarbonate is dissolved, under an argon atmosphere, in DMF (30 ml) then the reaction medium is heated at a temperature of 80 C. for 18 hours. The reaction mixture is cooled down to 0 C. and ice-cooled water is added. The reaction mixture is extracted with ethyl acetate and the organic phase is washed successively with 50 ml of water and 50 ml of salt water, dried over magnesium sulphate, filtered and concentrated under vacuum. The evaporation residue is purified by trituration with isopropyl ether and the solid obtained is filtered and rinsed with isopentane in order to obtain after drying 2.0 g of a solid yellow product (yield 100%). Melting point: 109-110.5 C.

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

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6605637; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 36282-26-5, A common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at -78 C was added EtMgBr (18.3 mL,55 mmol) drop wise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et20 (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HC1 solution, and washed with EtOAc. The aqueous layer was adjusted to pH~10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3 x). The combined organic layers were dried over anhy.Na2S04, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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Reference of 123-06-8,Some common heterocyclic compound, 123-06-8, name is Ethoxymethylenemalononitrile, molecular formula is C6H6N2O, 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.

A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate -hexane followed by ether to afford the title compound as light pale brown crystals (5.6 g, 64.4 %); LC/MS, API-ES, Neg, (M-H)”, 163.0.

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

Reference:
Patent; FOLDRX PHARMACEUTICALS, INC.; WHITEHEAD INSTITUTE FOR BIOMEDICAL RESEARCH; WO2007/126841; (2007); A2;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6N2O2

NaH (4.34 g, 90.4 mmol) was stirred in a solvent of tetrahydrofuran (20 mL) at 0 C. The reaction solution was slowly added with 2-(3-nitrophenyl)acetonitrile (2.2 g, 13.6 mmol), and stirred for about 30 minutes at 0 C. The reaction solution was added with MeI (6.67 mL, 107 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was added with an ice water. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (EA:HEX=1:9) to obtain the title compound (0.6 g, 23%). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 8.33 (s, 1H), 8.22 (d, 1H), 7.91 (d, 1H), 7.65 (t, 1H), 1.81 (s, 6H). MS (ESI+, m/z): 191 [M+H]+

According to the analysis of related databases, 621-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI PHARM. CO., LTD.; Bae, In Hwan; Han, Sang Mi; Kwak, Eun Joo; Ahn, Young Gil; Suh, Kwee Hyun; US2015/191450; (2015); A1;,
Nitrile – Wikipedia,
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