Category: nitriles-buliding-blocks

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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 1735-53-1

Description for D664-(1 -Cyclohexen-1 -yl)-3-(trifluoromethyl)benzamide (D66)4-bromo-3-(trifluoromethyl)benzonitrile (commercial) (1.2 g, 4.80 mmol), 1- cyclohexen-1-ylboronic acid (0.907 g, 7.20 mmol), sodium methoxide (0.778 g, 14.40 mmol) and bis(triphenylphosphine)palladium(ll) chloride (0.337 g, 0.480 mmol) were added to dry methanol (12 ml.) and the mixture heated in the microwave at 80 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate (40 ml.) and water (40 ml.) and then the organic phase washed with further water (40 ml_). The organic phase was dried (MgSC^), filtered and the solvent removed in vacuo. The crude product was purified by flash silica chromatography, eluting with 0-75 % ethyl acetate in hexane to give the title compound as a white solid (1.02 g). deltaH (CDCI3, 400 MHz): 8.09 (1 H, m), 7.90 (1 H, dd), 7.32 (1 H, d), 6.3-5.8 (2H, m) 5.61 (1 H, s), 2.25-2.13 (4H, m), 1.80-1.60 (4H, m). MS (ES): C14H14F3NO requires 269; found 270 (MH+).

The synthetic route of 1735-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74821; (2008); A1;,
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Application of 1558-81-2, 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. 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To concentrated sulfuric acid (102 mL) was added 1-cyano-cyclopropanecarboxylic acid ethyl ester (60 g, 0.43 mol) dropwise followed by 2-methylpentan-2,4-diol (52 g, 0.44 mmol) dropwise at 0 C. The mixture was stirred for an additional 1 h at 0 C. then poured onto ice-water. The aqueous phase was washed with AcOEt (3¡Á200 mL) and then basified to pH 12 with 10 M NaOH. The resulting mixture was extracted with EtOAc (3¡Á500 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester (65 g, yield: 63.2%). 1H NMR (CDCl3 400 MHz): delta4.21-4.06 (m, 311), 1.73-1.69 (m, 1H), 1.40-1.10 (m, 1711)

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 1-Cyano-1-cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
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Some common heterocyclic compound, 623-03-0, name is 4-Chlorobenzonitrile, molecular formula is C7H4ClN, 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: 623-03-0

General procedure: Microwave assisted reactions were carried out in a domestic microwave oven (Samsung-LCE 2733 GXTL) for realistic control of the microwaves operating at 850 W generating 2450MHz frequency through out the required time.A mixture of nitrile (0.01 mol), ethylenediamine (0.04 mol) and carbon disulphide solvent (0.001mol) was taken in a Erlenmeyer flask. The Erlenmeyer flask was placed in a microwave ovenand irradiated under at low power (100 W) for 30-150 seconds. The completion of the reactionwas monitored by TLC using ethyl acetate: methanol (4:1) as eluent. The reaction mixture wascooled at room temperature. Cold water (20 mL) was added to it and then extracted withchloroform (3 x 25 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated.Crystallization of the crude product from cyclohexane gave the pure product in 70-80% yields(Table 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 623-03-0, its application will become more common.

Reference:
Article; Pathan, Mohsin Y.; Paike, Vijaykumar V.; Pachmase, Pandurang R.; More, Sandeep P.; Ardhapure, Suresh S.; Pawar, Rajendra P.; ARKIVOC; vol. 2006; 15; (2006); p. 205 – 210;,
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Electric Literature of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

Synthesis Example 6: Synthesis of 3,4,6-trichloro-5-(2-bromo-phenoxy)-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.25 g of 2-bromophenol, 3.9 g of K2CO3, and 25 ml of N,N-dimethyl formamide were put in a 100 ml flask, and then stirred while heated at 70¡ã C. When the reaction was complete, EA (ethyl acetate) was used for an extraction. After the extraction, the resultant was concentrated to obtain a solid. Herein, the obtained solid was dissolved in an small amount of dichloromethane, several times washed with hexane, filtered, and vacuum-dried to obtain 3,4,6-trichloro-5-(2-bromo-phenoxy)-phthalonitrile.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 403-54-3, name is 3-Fluorobenzonitrile, 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 403-54-3, Recommanded Product: 3-Fluorobenzonitrile

3-(4-Benzyl-piperazin-1-yl)-benzonitrile (49b). To a mixture of 3-fluoro-benzonitrile 43b (1.0 g, 8.25 mmol) and K2CO3 (2.27 mg, 16.51 mmol) in dimethyl sulfoxide (7 mL) was added 1-benzyl piperazine (2.14 mL, 12.38 mmol) and the reaction continued as described above to afford amine 199 g of 49b in 87% yields. 1H-NMR (500 MHz, CDCl3): delta 2.65 (4Hs, t, J=5.12 Hz), 3.27 (4Hs, t, J=5.12 Hz), 3.61 (2Hs, s), 7.11-7.15 (3Hs, m), 7.31-7.41 (6Hs, m); ESI-MASS: 300.5 (M+23).

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; University of Tennessee Research Foundation; US2005/222408; (2005); A1;,
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Synthetic Route of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

(v) 2-Cyano-N-[5-(4-(1,1-dimethylethyl)phenyl)thien-2-yl]-3-hydroxybut-2-enamide A suspension of cyanoacetone, sodium salt (40.98 g); in freshly sodium dried and distilled tetrahydrofuran (200 ml) was mechanically stirred and cooled in an ice-bath. A slightly turbid solution of 2-[4-(1,1-dimethylethyl)phenyl]-5-isocyanatothiophene (100 g), in dry tetrahydrofuran (400 ml) was added dropwise during 40 minutes at 3-5 C. After stirring the mustard coloured suspension in the ice-bath for a further 20 minutes, the bath was then removed, stirring continued for 52 minutes at ambient temperature, then for 1.5 hours at 55 +-2 C. in a heating mantle. After evaporation in vacuo the residual cream coloured paste was stirred in 0.7 N sodium hydroxide (975 ml) for 30 minutes. Filtration removed an insoluble cream coloured solid. The alkaline filtrate was adjusted to pH 1 by the addition of concentrated hydrochloric acid, precipitating a cream coloured pasty solid which was removed by filtration, washed with water (approximately 3 1) and partially dried at 60 C. in vacuo. This solid was stirred at reflux in absolute ethanol (2 1) for 15 minutes, then for 45 minutes in an ice-bath. After filtration, washing with ice-cold ethanol (400 ml) and drying at 60 C. in vacuo. It was further purified by stirring for 10 minutes with charcoal (5 g) in boiling ethyl acetate (2.25 1). The charcoal was removed by filtration and washed on the filter with hot ethyl acetate (300 ml). The filtrate and washings were combined and reduced in volume by 1.5 1 by evaporating in vacuo. After standing in an ice-bath for 1 hour, pale green crystals were removed by filtration, washed with 40-60 C. petrol (100 ml) and dried at 45 C. in vacuo. The crystalline solid was finally purified by stirring in 1N sodium hydroxide (750 ml) and ether (750 ml). The lower aqueous alkaline layer was removed and filtered to clarify. Concentrated hydrochloric acid was added to adjust to pH 1. The resulting cream coloured precipitated solid was filtered off, washed on the filter with water (2 1) and dried at 60 C. in vacuo, m.p. 226-228 C.

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

Reference:
Patent; Lilly Industries Limited; US4983619; (1991); 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. 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Methyl-2-(4-nitrophenyl)propanenitrile

16 g (84.1 mmol) of 2-methyl-2-(4-nitro-phenyl)-propionitrile (Example 1d) and 4.16 g of Raney-Ni are shacked in 160 ml of THF-MeOH (1 :1) under 1.1 bar of H2 for 12 h at rt. After completion of the reaction, the catalyst is filtered-off and the filtrate is evaporated to dryness. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 3:1 to 1 :2) to provide the title compound as an oil. ES-MS: 161 (M + H)+; analytical HPLC: W= 2.13 minutes (Grad 1).

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 71825-51-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/122806; (2006); A2;,
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Electric Literature of 25309-65-3,Some common heterocyclic compound, 25309-65-3, name is 4-Ethylbenzonitrile, molecular formula is C9H9N, 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.

Step A. Methyl 4-ethylbenzenecarboximidoate Hydrodrochloride Hydrogen chloride gas was bubbled through a methanol solution of 4-ethylbenzonitrile (5.0 g, 38.11 mmol) at 0 C. for 30 minutes. The reaction was sealed and stood at ambient temperature overnight. The solvent was removed in vacuo and the oily residue triturated with diethyl ether. The resulting solid was removed to yield the title compound which was stored in a dry atmosphere.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Ethylbenzonitrile, its application will become more common.

Reference:
Patent; American Home Products Corporation; US2002/22638; (2002); A1;,
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These common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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. Computed Properties of C8H11N

(3R)- and (3S)-3-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile[0112] To a solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine(15.0 g, 0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cisand trans isomers), followed by DBU (15 mL, 0.10 mol).The resulting mixture was stirred at room temperatureovernight. The ACN was evaporated. The mixture wasdiluted with ethyl acetate, and the solution was washedwith 1.0 N HCl. The aqueous layer was back-extractedwith three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodiumsulfate, filtered and concentrated. The crude product waspurified by silica gel chromatography (gradient of ethylacetate/hexanes) to yield a viscous clear syrup, whichwas dissolved in ethanol and evaporated several timesto remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H, 15percent ethanol/hexanes) and usedseparately in the next step to generate their corresponding final product. The final products (see Step 3) stemming from each of the separated enantiomers were foundto be active JAK inhibitors; however, the final productstemming from the second peak to elute from the preparative-HPLC was more active than its enantiomer.1H NMR (300 MHz, CDCl3): delta8.85 (s, 1H), 8.32 (s, 2H),7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H), 3.54(t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H),2.03-1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H), -0.06(s, 9H); MS(ES):437 (M+1).

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

Reference:
Patent; Incyte Holdings Corporation; FRIEDMAN, Paul A.; FRIDMAN, Jordan S.; LUCHI, Monica E.; WILLIAMS, William V.; (27 pag.)EP2349260; (2016); 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. 288309-07-9, name is 5-Acetyl-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 5-Acetyl-2-fluorobenzonitrile

To a stirred solution of the ketone (4-d, 106 mg, 0.65 mmol) in CH2Cl2 (5 mL) was added at 0 C dropwise [bis(2-methoxyethyl)amino]sulfur trifluoride (717 mg, 3.25 mmol). The reaction mixture was stirred at room temperature for 1 h, portioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. The crude product was diluted in MeOH (10 mL) and stirred under H2 atmosphere in the presence of Pd/C (50 mg). After 3 h, the reaction mixture was filtered and the filtrate solution was concentrated in vacuo. The crude amine was diluted with CH2Cl2 (5 mL) and reacted with 2-phenylbutanoyl chloride (119 mg) in the presence of DIEA (0.45 mL, 2.6 mmol). After 3 h, the reaction mixture was concentrated in vacuo and chromatographed (SiO2, 20% ethyl acetate in hexanes) to give the desired product (1-29); HRMS (M+1)=336.1573; 1H NMR (500 MHz, CDCl3) 7.27 (m, 7H), 7.04 (t, 1H, J=8.5 Hz), 5.78 (s, 1H), 4.47 (d, 1H, J=6.0 Hz), 3.28 (t, 1H, J=7.5 Hz), 2.21 (m, 1H), 1.82 (t, 1H, J=18.0 Hz), 0.89 (t, 1H, J=7.5 Hz)

The synthetic route of 288309-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanney, Barbara; Kim, Yuntae; Krout, Michael R.; Meissner, Robert S.; Mitchell, Helen J.; Musselman, Jeffrey; Perkins, James J.; Wang, Jiabing; US2005/277681; (2005); A1;,
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