Author: Jessica.F

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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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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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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-3-nitrobenzonitrile

Example 1732- [4-(l-Benzofuran-5-yl)phenyl]-l-{[(3S)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl] methyl}- lH-benzimidazole-7-carbonitrile(a) 2-({[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amino)-3- nitrobenzonitrileA mixture of {[(3S)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amine (553 mg, 3.29 mmol), 2-chloro-3 -nitrobenzonitrile (500 mg, 2.74 mmol), and DIEA (1.431 mL, 8.22 mmol) were dissolved in 1,4-dioxane (10 mL) in a microwave Vial. The mixture was heated at 150 C for 1 hour. The mixture was evaporated, taken up in DCM and washed with water. The aqueous layer was extracted with DCM and the combined organics evaporated and purified by silica gel column chromatography using a gradient of 0-5% MeOH/DCM to afford the titled compound (800 mg, 2.55 mmol, 93 % yield) as an orange solid. 1H NMR (400 MHz, chloroform-d) delta ppm 0.71-0.88 (m, 2 H) 0.94-1.12 (m, 2 H) 1.59-1.69 (m, 1 H) 1.69-2.00 (m, 1 H) 2.11-2.41 (m, 1 H) 2.55-2.92 (m, 0 H) 3.16-4.11 (m, 6 H) 6.80 (ddd, J=10.04, 8.40, 7.58 Hz, 1 H) 7.79 (ddd, J=9.35, 7.71, 1.39 Hz, 1 H) 8.27- 8.49 (m, 1 H) 8.53-8.80 (m, 1 H).

According to the analysis of related databases, 34662-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HALLMAN, Jason; LAUDEMAN, Christopher; LIU, Ronggang; MILLER, Aaron; MOORE, Michael, Lee; DOCK, Steven; MUSSO, David; PARRISH, Cynthia; WO2011/56635; (2011); 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, 80517-21-1, name is 4-Fluoro-2-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. Recommanded Product: 4-Fluoro-2-nitrobenzonitrile

4-fluoro-2-nitrobenzonitrile (0.2 mmol, 33.2 mg), tetrahydroxydiboron (0.6mmol, 53.8 mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), Benzaldehyde (0·24mmol, 25·4mg), methanol (1ml), water (1ml) were added to the test tube, reacted at 60 C for 3h, after the completion of reaction, the reaction solution was extracted with ethyl acetate three times, the combined organic phases are concentrated to dryness, separated through column chromatography (petroleum ether: ethyl acetate =4:1), Yield:(45.0mg,93%)

The synthetic route of 4-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Zhou Haifeng; Sui Yuebo; Jiang Xiaolan; Yang Bing; Yu Tao; (16 pag.)CN108558778; (2018); 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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Reference of 69797-49-5, The chemical industry reduces the impact on the environment during synthesis 69797-49-5, name is 2-Amino-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 2-amino-3- methylbenzonitrile (0.85 g, 6.4 mmol) in THF (17 ml) was added triethylamine (0.99 ml, 7.1 mmol) followed by phosgene (20 % in toluene, 3.41 ml, 6.4 mmol). The RM was heated at reflux for 4 h then allowed to cool to RT. The THF was evaporated in vacuo and the residue precipitated with cold pentane. The resulting mixture was filtered and the filtrate evaporated to give the title compound as a yellow oil. Y = 74 %. MS ES+: 232.0 (compound analysed in diethylamine to generate diethyl urea).

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-Amino-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (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. 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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Adding a certain compound to certain chemical reactions, such as: 97582-88-2, name is 3-(Difluoromethoxy)benzonitrile, 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 97582-88-2, Safety of 3-(Difluoromethoxy)benzonitrile

(1) A Grignard reagent prepared by using 0.75 g of magnesium, 4.46 g of 2-bromopropane and 24 ml of anhydrous diethyl ether, was dropwise added to a mixture comprising 4.09 g of 3-difluoromethoxybenzonitrile and 20 ml of anhydrous diethyl ether. After completion of the dropwise addition, the mixture was reacted at room temperature for 27 hours. The reaction mixture was put into ice water, and 6N sulfuric acid was added to bring the mixture to be weakly acidic, followed by stirring for 0.5 hour. The mixture was extracted with diethyl ether and washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=l/19), to obtain 2.04 g of 3-difluoromethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.XH-NMR 5ppm (Solvent: CDCl3/300 MHz)1.23(d,6H),3.52(m,lH),6.56(t,lH),7.32(dd,lH),7.48(t, 1H),7.70(s,lH),7.80(d,lH)

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; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (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. 61272-77-3, name is 2-Amino-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 61272-77-3

Synthesis Example 13 1-benzyl-6-fluoro-2,3-dihydro-1H-pyrrolo [2,3-b] quinoline-4-ylamine hydrochloride Phosphorus oxychloride (0.51 ml) was added to a solution of 1-benzyl-2-pyrrolidone (0.84 ml) in chloroform (3 ml). The solution was stirred at room temperature for 30 minutes, and 2-amino-5-fluorobenzonitrile (0.65 ml) was added thereto. The reaction mixture was refluxed for 3 hours while heating and then ice-water was added thereto. Further, the mixture was neutralized by adding 20% aqueous sodium hydroxide solution and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene) amino} benzonitrile (1.68 g).

According to the analysis of related databases, 61272-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tarui, Naoki; Santo, Takashi; Mori, Masaaki; Watanabe, Hiroyuki; US2003/139442; (2003); A1;,
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