Month: February 2021

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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 658-99-1

91.1.1 Synthesis of 3-cyano-3-(3,4-difluoro-phenyl)pentanedioic acid diethyl ester Cool a solution of sodium bis(trimethylsilyl)amide (686 mL, 1M in tetrahydrofuran, 686 mmol) to about -10 C. Add a solution of 3,4-difluoro-phenylacetonitrile ((50 g, 326 mmol) in tetrahydrofuran (130 mL) over about 1.5 hours. When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir for 2 hour. Cool a solution of ethyl bromoacetate (120 mL, 718 mmol) in tetrahydrofuran (250 mL) in a dry-ice/isopropanol bath. Transfer the above solution via cannula into the solution of ethyl bromoacetate over about 35 minutes. Warm to ambient temperature. After 18 hours, dilute with diethyl ether (300 mL) and extract water, a 1M hydrochloric acid solution, a saturated aqueous solution of sodium bicarbonate, and then a saturated aqueous solution of sodium chloride. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give the title compound to give the title compound.

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; Hoechst Marion Roussel Inc.; US5824690; (1998); A;,
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These common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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. COA of Formula: C7H13NO2

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

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

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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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. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 939-79-7

B. 4-Cyano-2-nitrobenzoic acid. To a 0 C. solution of 4-methyl-3-nitrobenzonitrile (5.0 g, 0.031 mol) in H2SO4 (83 mL) was added dropwise over 2 h a mixture of Na2Cr2O7 (14 g, 0.047 mol) and H2SO4 (15 mL). The reaction mixture was allowed to warm to room temperature with stirring over 48 h. The resulting green mixture was poured onto crushed ice, and the precipitate was collected by filtration. The filtered solids were dissolved in 5% aq. Na2CO3 (60 mL) and the residual solids were removed by filtration. The filtrate was treated with dilute HCl and the resulting precipitate was collected by filtration and dried in air to provide the title compound as a white solid (2.7 g, 46%). 1H NMR (500 MHz, CD3OD): 8.39 (d, J=1.3 Hz, 1H), 8.12 (dd, J=8.0, 1.3 Hz, 1H), 8.00 (d, J=8.0, 1H).

The synthetic route of 939-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allison, Brett D.; Hack, Michael D.; Phuong, Victor K.; Rabinowitz, Michael H.; Rosen, Mark D.; US2005/38032; (2005); A1;,
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Application of 326-62-5,Some common heterocyclic compound, 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, molecular formula is C8H6FN, 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 B To the 2-fluorophenylacetonitrile (0.80 g, 5.92 mmol), benzyltriethyl-ammonium chloride (0.03 g, 0.12 mmol), and 1-bromo-2-chloroethane (1.70 g, 11.9 mmol) was added 50% aqueous NaOH (3.5 ml).. The reaction was stirred at 45 C. for 21 h and ethylene glycol was added (3 ml).. The reaction was then warmed to 100 C. and stirred for 7 h.. Upon cooling to RT, the reaction was diluted with water and washed with EtOAc. The aqueous layer was acidified to PH 2-3 with aqueous 6N HCl. The acidified solution was extracted with Et2O. The combined Et2O extracts were washed with water and brine and dried (MgSO4).. Filtration and evaporation of the solvent in vacuo afforded a pale yellow solid (1.06 g, 99%).. The arylcyclopropyl acid was coupled to the product of example 8, step 3, using the procedure of Example 8, step 4 to obtain 24B as the HCl salt. HRMS (M+H): found 532.2949.

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

Reference:
Patent; Schering Corporation; US6391865; (2002); B1;,
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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., Quality Control of 2-Bromo-4-methylbenzonitrile

2-(2,5-Dimethoxypyridin-4-yl)-4-methylbenzonitrile 2.50 g (9.36 mmol) of diisopropyl (2,5-dimethoxypyridin-4-yl)borate, 3.88 g (28.08 mmol, 3 eq.) of potassium carbonate and 0.764 g (0.936 mmol, 0.1 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct were initially charged in a flask, which was then evacuated and filled with argon three times. 2.27 g (11.23 mmol, 1.2 eq) of 2-bromo-4-methylbenzonitrile and 68 ml of dioxane were added, argon was passed through for 2 min and the mixture was stirred at 100 C. overnight. The reaction mixture was filtered through kieselguhr and washed with dichloromethane/methanol 9:1, and the filtrate was concentrated. The crude product was purified by means of Biotage-Isolera (eluent: cyclohexane/ethyl acetate, 0-40%). Yield: 1.72 g (71% of theory). LC/MS [Method 1]: Rt=1.00 min; MS (ESIpos): m/z=255 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.03 (s, 1H), 7.81 (d, 1H), 7.42 (d, 1H), 7.37 (s, 1H), 6.78 (s, 1H), 3.85 (s, 3H), 3.78 (s, 3H), 2.42 (s, 3H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; STAMPFUss, Jan; (82 pag.)US2017/298052; (2017); A1;,
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These common heterocyclic compound, 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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. HPLC of Formula: C11H9NO2

General procedure: To a solution of 1 (0.10 mmol, 1.0 equiv.), [(TMEDA)Ni(o-tolyl)Cl] (1.6 mg, 0.0050 mmol, 5.0 mol %),and PMePh2 (1.9 L, 0.010 mmol, 10 mol %) in THF (1.0 mL, 0.10 M) under an argon atmosphere was added Et2Zn (1.0 M in hexanes, 0.15 mL, 0.15 mmol, 1.5 equiv) at 0 C. After being stirred the mixture at 30 C for the indicated reaction time judged by TLC analysis, the electrophile (2.0 equiv) was added tothe reaction solution at 30 C unless otherwise noted. The reaction mixture was stirred at the indicated temperature for the indicated reaction time. The reaction was quenched by the addition of sat. aq. NH4Cl.The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organiclayer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified byflash column chromatography (hexane/EtOAc or hexane/CH2Cl2/EtOAc) on silica gel to afford corresponding product.

The synthetic route of Methyl (E)-2-Cyano-3-phenylacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsujihara, Tetsuya; Tomeba, Moriho; Ohkubo-Sato, Shigeaki; Iwabuchi, Kyoko; Koie, Rino; Tada, Natsumi; Tamura, Satoru; Takehara, Tsunayoshi; Suzuki, Takeyuki; Kawano, Tomikazu; Tetrahedron Letters; vol. 60; 42; (2019);,
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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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H5NO

General procedure: 3-Acetyl-2-aminothiophene Derivatives; General Procedure Carbonyl compound (0.025 mol) was added to freshly prepared cya-noacetone (0.03 mol) in either MeOH or EtOH (40 mL). Sublimed sul-fur S8 (0.03 mol) and piperidine (0.03 mol) were added and the mix-ture was stirred and heated to 55-65 C for 24 h. Ice was then addedand the formed precipitate was filtered under vacuum and washedwith water. The obtained solid was crystallised from a suitable sol-vent, with the exception of 4g and 4j, which were collected directlywithout further purification.

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 2469-99-0.

Reference:
Article; Abdelwahab, Ahmed B.; Hanna, Atef G.; Kirsch, Gilbert; Synthesis; vol. 48; 17; (2016); p. 2881 – 2888;,
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Application of 2032-34-0,Some common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, molecular formula is C7H13NO2, 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 round bottom flask was added the methane sulfonic acid salt of methyl l-amino-4-bromo-lH-pyrrole-2-carboxylate (140 g, 0.444 mol), isopropanol (700 mL) and 3,3- diethoxypropionitrile (128 g, 0.888 mol). The reaction mixture was slowly brought to 85 C over 1 hour and then stirred at 85 C for 2 hours. At this time, the ethanol that was generated and the isopropanol was removed under vacuum. The resulting residue was dissolved in CH2CI2 and washed with water and brine solution. The organic layer was separated, dried over Na2S04, filtered and concentrated. The resulting residue was transferred into a 2L round bottom flask and dichloroethane (900 mL) and DBU (210 gm, 1.36 mol) were successively added to the reaction mixture. The resulting mixture was then stirred at 85 C for 5 hours then cooled to rt and diluted with CH2CI2 followed by washing with water then brine solution. The organic layer was separated, dried over Na2S04, filtered and concentrated. The resulting residue was purified by flash silica gel column chromatography to yield 58 g of title compound as the crude product containing residual DBU. This material was used as is in the next transformation. LCMS (condition A) m/z = 236.0 -ve. XH NMR (400MHz, DMSO-d6) delta ppm: 9.76 (1H, br.s), 7.62 (1H, s), 7.39 (1H, d, 2.0Hz), 6.43 (lH,d, 2.0 Hz). The product is contaminated with DBU and was used directly as such without further purification in the next step.

The synthetic route of 2032-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; BROWN, Gregory D.; DOWEYKO, Lidia M.; DUAN, Jingwu; GUO, Junqing; HYNES, John; JIANG, Bin; KEMPSON, James; LIN, Shuqun; LU, Zhonghui; SPERGEL, Steven, H.; TOKARSKI, John S.; WU, Hong; YANG, Bingwei Vera; WO2012/125886; (2012); A1;,
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Synthetic Route of 621-03-4,Some common heterocyclic compound, 621-03-4, name is 2-Cyano-N-phenylacetamide, molecular formula is C9H8N2O, 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.

c) 5-amino-4-methyl-7-oxo-N-phenyl-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide Under argon 46 mg sodium hydride (1 .15 mmol, 60% in mineral oil) in 2 mL DMF were cooled to 0 C and 94 mg 2-cyano-N-phenylacetamide (0.58 mmol) were added in small portions within 15 minutes, the resulting solutino was stirred for another 30 minutes at r.t., then cooled to 0 C and 97 mg 1 -methyl-1 H-thieno[3,2-d][1 ,3]oxazine-2,4-dione (0.52 mmol) were added in portions within 5 minutes and the mixture was stirred for 60 minutes. To this solution 0.58 mL aqueous hydrochloric acid (1 .15 mmol) were added and the resulting yellow suspension was stirred for 10 minutes. The mixture was poured on icecold potassium bicarbonate solution (10%, w/v), stirred for 30 minutes, filtered and the solid washed with water, diethylether / pentane (3:2, v/v), pentane and dried to yield 68 mg 5-amino-4-methyl-7- oxo-N-phenyl-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (0.21 mmol, 40%) as a yellow solid. ESI-MS [M+H] + 300.2 1H-NMR (400 MHz, D6-DMSO): delta (ppm) = 7.97-7.80 (m, 1 H), 7.61 -7.49 (m, 2H), 7.43-7.27 (m, 2H), 7.17-7.07 (m, 1 H), 6.94-6.81 (m, 1 H), 3.03-2.91 (m, 3H).

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

Reference:
Patent; NOVARTIS AG; REINHARDT, Juergen; SCHMIEDEBERG, Niko; SPANKA, Carsten; WO2015/186061; (2015); A1;,
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Electric Literature of 3672-47-7, The chemical industry reduces the impact on the environment during synthesis 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, I believe this compound will play a more active role in future production and life.

To a stirred solution of 0.30 g (1.71 mmol) 3-(4-methoxy-phenyl)- 3-oxo-propionitrile in 10 ml ethanol was added 0.17 ml (1.71 mmol) cyclohexanone, 53 mg (1.71 mmol) sulfur, EPO and 0.14 ml (1.71 mmol) morpholine. The mixture was heated at 40 0C for the week end, and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 0.51 g (85%) (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-(4- methoxy-phenyl)-methanone as an orange solid. ES-MS m/e (%): 288 (M+H+, 100).

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, 3-(4-Methoxyphenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2006/63732; (2006); A1;,
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