Month: January 2021

Reference of 4110-35-4,Some common heterocyclic compound, 4110-35-4, name is 3,5-Dinitrobenzonitrile, molecular formula is C7H3N3O4, 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: A mixture of nitrile (1 mmol), sodium azide (1.5 mmol), Cu complex catalyst (0.4 mol%) and DMF (3 mL) was taken in a round-bottomed flask and stirred at 110 C temperature. After completion of the reaction the catalyst was separated from the reaction mixture with an external magnet and reaction mixture was treated with ethyl acetate (2 ¡Á 20 mL) and 1 N HCl (20 mL). The resultant organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2 ¡Á 15 mL). The combined organic layers were washed with water, concentrated, and the crude material was chromatographed on silica gel (Hexane-EtoAc, 1:1) to afford the pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dinitrobenzonitrile, its application will become more common.

Reference:
Article; Esmaeilpour, Mohsen; Javidi, Jaber; Nowroozi Dodeji, Fatemeh; Mokhtari Abarghoui, Mehdi; Journal of Molecular Catalysis A: Chemical; vol. 393; (2014); p. 18 – 29;,
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Some common heterocyclic compound, 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, molecular formula is C8H5F3N2, 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. Formula: C8H5F3N2

a) 2-Trifluoromethyl-biphenyl-4-carbaldehyde oximeStep a) To a solution of 4-cyano-2-trifluoroaniline (1 eq) in benzene there is added under inert atmosphere n-pentylnitrite (1 eq) at 5O0C. After one hour refluxing a second equivalent of n-pentylnitrite is added. After additional two hours of refluxing the reaction mixture is cooled to room temperature and concentrated under reduced pressure. The dark residue is purified on silica gel using c-hexane-> c-hexane/ethyl acetate 9/1 as mobile phase (pale orange oil).; Step a) To a solution of 4-cyano-2-trifluoroaniline (1 eq) in benzene there is added under inert atmosphere n-pentylnitrite (1 eq) at 5O0C. After one hour refluxing a second equivalent of n-pentylnitrite is added. After additional two hours of refluxing the reaction mixture is cooled to room temperature and concentrated under reduced pressure. The dark residue is purified on silica gel using c-hexane-> c-hexane/ethyl acetate 9/1 as mobile phase (pale orange oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-74-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/85451; (2007); A2;,
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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 57381-49-4 as follows. Quality Control of 2-Bromo-4-chlorobenzonitrile

2-bromo-4-chlorobenzonitrile 1 g (1.18 g, 5.48 mmol) and 1f (1.3 g, 5.48 mmol) were added to 20 mL of 1,4-dioxane, followed by[1,1′- (Diphenylphosphino)ferrocene]dichloropalladium (240 mg, 0.33 mmol) and potassium carbonate(2.3 g, 16.4 mmol) were added. The reaction mixture was heated to 100-110C and the reaction was stirred for 16 hours.The reaction solution was allowed to cool to roomtemperature and 50 mL of water was added to the reaction mixture. The mixture was extracted with ethyl acetate (50 mL ¡Á 3). The organic phases were combined and the organic phase was washed with water(50 mL) and saturated sodium chloride solution (50 mL). After drying over anhydrous sodium sulfate, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedwith aCombiFlash flash reader using eluent system B to give the title product 1h (570 mg, colorless oil), yield: 31.6%.

According to the analysis of related databases, 57381-49-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
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Application of 26830-95-5, 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 26830-95-5 as follows.

a 2-Amino-4-methylbenzonitrile A mixture of 4-methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) and 10% palladium on carbon (500 mg) in 1,4-dioxane (60 mL) was stirred under hydrogen (balloon) overnight. The catalyst was removed by filtration through the Celite, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane) to give the title compound as a pale yellow solid (3.3 g, 83%). 1 H-NMR (300 MHz, CDCl3) delta 7.26 (d, J=8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H).

According to the analysis of related databases, 26830-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US5891909; (1999); A;,
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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. 52864-54-7, name is 2-(2-Bromo-4-chlorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Formula: C8H5BrClN

To a stirred suspension of NH4Cl (9.241 g, 169.565 mmol) in dry toluene (120 mL) was added tri-methyl aluminum (2 M) (45.23 mL, 90.435 mmol) at 5 C. the reaction mixture was warmed to room temperature and the reaction mixture was stirred for 2 h. A solution of (2-bromo-4-chlorophenyl)-acetonitrile (374) (13 g, 56.522 mmol) in toluene (30 mL) was added to the above reaction mixture and the reaction mixture was stirred for 14 h at 80 C. while silica thin layer chromatography was performed (10% methanol in dichloromethane; Rf=0.2). After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel (20 g) in chloroform (200 mL) and the reaction mixture was stirred for half an hour at room temperature and filtered. The silica gel was washed with methanol (100 mL) and the combined filtrate was concentrated under reduced pressure to get 2-(2-bromo-4-chlorophenyl)-acetamidine hydrochloride (375) (14.0 g, 87.68%) as a white solid. [1341] LC-MS: 248.8 (M+H)

The synthetic route of 52864-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); A1;,
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Some common heterocyclic compound, 56043-01-7, name is 2-Amino-6-methylbenzonitrile, molecular formula is C8H8N2, 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 2-Amino-6-methylbenzonitrile

General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56043-01-7, its application will become more common.

Reference:
Article; Sutherell, Charlotte L.; Ley, Steven V.; Synthesis; vol. 49; 1; (2017); p. 135 – 144;,
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Electric Literature of 42872-73-1, A common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, molecular formula is C8H6BrN, 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 solution of 2-bromo-4-methylbenzonitrile (4.0 g; 20.40 mmol) in sulfuric acid (6mL) at 0C was added potassium nitrate (2.063 g; 20.40 mmol) in sulfuric acid (18mL). After stirring at 0C for 1.5 hour, the reaction mixture was poured into 500 mL ofice water. The precipitate was collected by filtration and washed with copious amountsof water. The precipate was dried to give 4.5 g (9 1%) of intermediate 455.

The synthetic route of 42872-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Synthetic Route of 198633-76-0, 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. 198633-76-0 name is 2-Fluoro-6-methylbenzonitrile, 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.

To a cooled (0 C) solution of 2-fluoro-6- methylbenzonitrile (5.0 g, 37 mmol) in 100 mL of concentrated H2SO4 was added NBS (6.93 g, 38.9 mmol). Then the mixture was stirred at 0 C for 3 hrs and poured into ice-water (1 L). The solution was extracted three times with EtOAc (200 mL) and the combined orgianc layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel flash chromatography to give the title compound

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-6-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; CATO, Brian; FRIE, Jessica, L.; KIM, Dooseop; PASTERNAK, Alexander; SHI, Zhi-Cai; WO2014/85210; (2014); A1;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 96784-54-2, name is 3-Methyl-4-nitrobenzonitrile, molecular formula is C8H6N2O2, 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. name: 3-Methyl-4-nitrobenzonitrile

4-cyano-3- methylnitrobenzene, 264 (1.5 g, 9.25 mmols) was suspended in 20 ml of water, sodium azide (0.661 g, 10.18 mmols) and zinc bromide (2.08 g, 9.25 mmols) were added. The reaction mixture was refluxed for 24 h with vigorous stirring. 15 ml of 3N HC1 and ethyl acetate (50 ml) were added, vigorous stirring was continued until no solid was present and the aqueous layer had a pH of 1. Phases were separated and the aqueous layer extracted with EtOAc (2 x 50 ml). The combined organic layers were evaporated under vacuum. The residue was dissolved in 100 ml of 0.25 N NaOH, and the mixture stirred for 30 min, until the original precipitate dissolved and a suspension of zinc hydroxide formed. The suspension was filtered, and the solid washed with 10 ml of 1 N NaOH. The filtrate was treated with 20 ml of 3 N HC1; the precipitated tetrazole was filtered, washed with 3 N HC1 (2 x 20 ml) and dried under vacuum. Yield 1.6 g (84 %). 1 H NMR (400 MHz, CDCl3) d 8.02 (d, 7 = 8.3 Hz, 1H), 7.68 (s, 1H), 2.63 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 96784-54-2, its application will become more common.

Reference:
Patent; ELEX BIOTECH, INC.; THAINASHMUTHU, Josephrajan; SIBRIAN-VAZQUEZ, Martha; BOATMAN, Douglas; (129 pag.)WO2019/191502; (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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-4-methylbenzonitrile

General procedure: To a stirred mixture of Ar-X (1, 1.0 mmol) and lithium bromide (208 mg, 2.4 mmol) in THF (3.5mL) was added dropwise a solution of i-PrMgBr in THF (2.0 M, 0.53 mL, 1.06 mmol) at -40C under Ar and the resulting mixture was stirred at -40C for 10 min and at room temperature for 3 h. To a stirred solution of dibromodifluoromethane (CF2Br2) in THF (4.90 M, 0.49 mL and 2.4 mmol) was added dropwise the prepared solution of ArMgBr 2 in THF via cannula at between room temperature and 35C over 1 min. and the resulting solution was stirred for 1 h. The reaction was quenched with saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (10 mL¡Á3). The combined extracts were dried over Na2SO4. Concentration of the solvent in vacuo afforded a residue, which was purified by silica gel column chromatography (hexane/EtOAc=10/1) and recycle GPC to give alpha,alpha-dibromo-alpha-fluorotoluene derivative 8.

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; Shiosaki, Masahiro; Inoue, Munenori; Journal of Fluorine Chemistry; vol. 175; (2015); p. 160 – 168;,
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