Tag: M.W=200-300

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;,
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Application of 129931-47-1, 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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Stage 1 1-(2-chloro-6-cyano-4-trifluoromethylphenyl)-5-(2-hydroxyisopropyl)-4-trifluoromethylpyrimidin-6-one was prepared from 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 5-(2-hydroxyisopropyl)-4-trifluoromethyl-pyrimidin-6-one (Preparation 2) according to the general method disclosed in EP 0 398 499 for the preparation of Compound A1 in Table A1. Melting Point: 125.6 – 127.6C, 1H NMR delta(CDCl3): 8.14(s,1H); 8.05(s,1H); 7.99(s,1H); 3.45(s,1H); 1.75(d,6H).

The synthetic route of 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; EP481604; (1992); A1;,
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These common heterocyclic compound, 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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. Quality Control of tert-Butyl 4-cyanobenzylcarbamate

To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75C for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N’-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

The synthetic route of tert-Butyl 4-cyanobenzylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co Ltd; kegami, Satoru; Watanabe, Atsushi; Hirano, Kimio; Oyama, Tadashi; (62 pag.)KR2016/18745; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 914250-82-1, name is 3-Bromo-2-chlorobenzonitrile, 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 914250-82-1, COA of Formula: C7H3BrClN

Description for D14 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (D14) A mixture of 3-bromo-2-chlorobenzonitrile (2.0 g), sodium bicarbonate (1.55 g) and hydroxylamine hydrochloride (1.28 g) in ethanol (50 ml.) was heated at reflux for overnight. The inorganic precipitate was filtered off. The solid was washed thoroughly with ethanol. The filtrate was concentrated. The obtained solid was dried in vacuo to afford 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (2.13 g). MS (ES): C7H6BrCIN2O requires 248; found 249.1 (M+H+).

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; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; MENG, Qinghua; REN, Feng; XIANG, Jianing; XU, Heng; ZHAO, Baowei; ZHANG, Haibo; WO2010/148649; (2010); A1;,
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Reference of 39786-34-0, 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. 39786-34-0, name is Ethyl 2-(2-cyanophenoxy)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 2000-mL round-bottom flask was placed a solution of KOtBu (18 g,160.41 mmol) in THF (600 mL) then a THF solution (400 mL) solution of ethyl 2-(2-cyanophenoxy)acetate (20 g,97.46 mmol,as prepared in the previous step) was added dropwise with stirring. After completion of addition,the reaction wasstirred at rt for 2 h,quenched by the addition of water,and extracted with EtOAc (3×200 mL).The organic extracts were combined,washed with brine (2×200 mL),dried over anhydrousNa2SO4,and concentrated under reduced pressure affording 17 g of the title compound as ayellow solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C,,H,2NO3: 206.1 (M+H); Found:206.1.

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, Ethyl 2-(2-cyanophenoxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
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These common heterocyclic compound, 453566-15-9, name is Methyl 3-bromo-5-cyanobenzoate, 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. category: nitriles-buliding-blocks

To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 %). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 %).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) delta 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).

The synthetic route of Methyl 3-bromo-5-cyanobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
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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. 320-41-2, name is 4-Chloro-2-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H3ClF3N

Add 4-chloro-2-trifluoromethyl-benzonitrile to formic acid (96percent) (15 mL) and water (3 mL). Add nickel-aluminun alloy (1260 mg). Heat at 100 0C overnight. Dilute with ethyl acetate and filter through Celite.(R).. Extract the filtrate with 1 N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 4-chloro-2-trifluoromethylbenzaldehyde (555 mg, 87percent): 1HNMR (400 MHz, MeOH-d4) delta 10.29 (m, IH), 8.10 (d, IH, J = 8.4 Hz), 7.91 (d, IH, J = 1.6 Hz)5 7.85 (dd, IH, J = 8.4, 1.6 Hz).

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; ELI LILLY AND COMPANY; WO2006/44454; (2006); 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. 51632-12-3, name is 2-(4-Bromophenyl)-3-methylbutanenitrile, A new synthetic method of this compound is introduced below., Formula: C11H12BrN

SYNTHESIS EXAMPLE 2 4-Bromo-alpha-isopropyl-phenylacetic acid 20 g of 4-bromo-alpha-isopropylphenylacetonitrile was heated with 140 ml of sulfuric acid (50V/V%) at 145 C for 6 hours. The cooled reaction mixture was poured onto 150 g of ice, and extracted with ether (100 ml * 3). The ether layers were combined and extracted with three 70 ml portions of cold 5% sodium hydroxide solution, and the aqueous extracts were acidified with concentrated hydrochloric acid, and then extracted with ether. The ether extract was washed successively with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate. Removal of the solvent gave 16.9 g (78.2%) of white crystals, which were sufficiently pure for use in next step. A portion of the crystals was recrystallized from benzene, melting point: 97 – 98 C.

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; Sumitomo Chemical Company, Limited; US3996244; (1976); A;,
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Application of 1114546-30-3, These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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.

Reference Example 3 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile To a solution of 4-bromo-2-fluoro-3-methylbenzonitrile (1.10 g), (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (1.18 g), cesium carbonate (2.51 g), tris(dibenzylideneacetone)dipalladium(0) (235 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (297 mg) in dioxane (30 mL) was stirred under an argon atmosphere at 80 C. for 8 hr. 5 The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (yield: 347 mg, 19%). 1H-NMR(CDCl3)delta:0.11(6H,d,J=7.2 Hz), 0.91(9H,s), 1.04(3H,d,J=6.4 Hz), 2.19(3H,d,J=2.3 Hz), 2.50(1H,dd,J=16.8,2.4 Hz), 2.78(1H,dd,J=16.8,5.4 Hz), 4.09-4.22(1H,m), 4.44-4.50(1H,m), 6.96(1H,d,J=8.7 Hz), 7.45-7.53(1H,m).

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); A1;,
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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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H2ClF4N

(c) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-pentafluoroethylpyrimidin-6-one (compound No 4 in Table I) was prepared by the reaction of 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 4-pentafluoroethylpyrimidin-6-one. 1 H NMR delta(CDCl3 /d6 -DMS0): 8.15 (1H,s); 8.09 (2H,m); 7.09 (1H,s).

The synthetic route of 129931-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts