Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 33279-01-5, name is 3-Oxopentanenitrile, 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 33279-01-5, Recommanded Product: 3-Oxopentanenitrile

A solution of 3-OXO-PENTANENITRILE (0. 5 g, 5.15 mmol) and methylhydrazine (0.24 g, 5. 15 mmol) in ethanol (5ML) is heated to reflux for 1.5 hours. The solvent is evaporated and the residue partitioned between ethyl acetate and brine. The organic phase is dried over MGS04 and evaporated to afford 5-ETHYL-2-METHYL-2H-PYRAZOL-3-YLAMINE. [M+H]

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Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/26113; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 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 4640-67-9, Computed Properties of C9H6FNO

General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.

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-Fluorophenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hill, Matthew D.; Synthesis; vol. 48; 14; (2016); p. 2201 – 2204;,
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Some common heterocyclic compound, 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, molecular formula is C11H19NO4, 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: Ethyl 2-cyano-4,4-diethoxybutyrate

Compound 44 (2.5 g, 10.7 mmol) and 2-cyano-4,4-diethoxy-butyric acid ethyl ester (3.2 g, 13.0 mol) were suspended in 15 mL of sodium ethoxide solution (2.8 g of sodium dissolved in 60 mL of ethanol), and the reaction mixture irradiated with microwave at 140 0C for 30 min. TLC (DCM: MeOH = 10:1) showed the starting material was reacted completely. The reaction mixture was cooled and evaporated under reduced pressure to get the residue, which was dissolved in a mixture of water (20 mL) and EtOAc (20 mL). The aqueous layer was extracted with EtOAc (20 mL x 3). The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the title compound (4.0 g, 90percent) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 52133-67-2, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 939-83-3, name is 2-Methyl-5-nitrobenzonitrile, 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 939-83-3, Computed Properties of C8H6N2O2

A mixture of 2-cyano-4-nitrotoluene (10 g, 6.17 mmol), benzaldehyde (6.51 g, 6.17 mmol) and potassium carbonate (20 g) in MeOH (200 mL) was heated at reflux for 10 min. The mixture was cooled to ambient temperature over 30 min, whereupon precipitation of the product was complete. The product was isolated by filtration and washed successively with 1N HCl, water and MeOH then air dried. There was obtained 13.0 g of the benzamide (mp 269.8 C.) as evident from the lack of a nitrile adsorption in the IR and the appearance of peaks at 3357.1, 3193.6 (-NH2) and 1648.7 cm-1 (H2NC(O)-); LRMS (M-NO)+ m/z=238.

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-Methyl-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DuPont Pharmaceuticals Company; US6339099; (2002); B1;,
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Electric Literature of 63069-50-1, 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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

(3) In the same manner as that described in Example 3(4), a reaction was carried out using 4-amino-3-fluorobenzonitrile (129 mg, 0.95 mmol), obtained in Example 25(2), trimethylaluminium (0.89 ml, 1.07M n-hexane solution, 0.95 mmol) and methyl 4-[(trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]benzoate (120 mg, 0.24 mmol), obtained in Example 12 (1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (134 mg, yield 92%) as a white solid which was recrystallized from ethyl acetate-hexane to give white powdery crystals. Melting point: 136 C. NMR spectrum (500 MHz, CDCl3) delta ppm: 1.22 (3H, d, J=7 Hz), 3.36 (1H, q, J=7 Hz), 3.4-3.6 (1H, m), 3.76 (1H, t, J=11 Hz), 3.79 (1H, t, J=11 Hz), 4.42 (1H, ddd, J=11, 5, 2 Hz), 4.55 (1H, ddd, J=11, 5, 2 Hz), 4.85 (1H, d, J=14 Hz), 5.05 (1H, d, J=14 Hz), 5.05 (1H, s), 5.55 (1H, s), 6.7-6.8 (2H, m), 7.3-7.4 (1H, m), 7.45 (1H, d, J=12 Hz), 7.53 (1H, d, J=8 Hz), 7.66 (2H, d, J=8 Hz), 7.79 (2H, s), 7.91 (2H, d, J=8 Hz), 8.22 (1H, bd, J=4 Hz), 8.73 (1H, t, J=8 Hz). IR spectrum: nu max (KBr) cm-1: 3435, 2232, 1686, 1520, 1139. Mass spectrum m/z (FAB): 610 (M++1).

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANKYO COMPANY, LIMITED; US2003/176480; (2003); A1;,
Nitrile – Wikipedia,
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Electric Literature of 1080-74-6, 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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a degassed solution of compound 10-5 (150 mg, 0.1 1 mmol) and pyridine (0.6 cm3) in anhydrous chloroform (40 cm3) at 0 C was added a degassed solution of 2-(3-oxo-indan-1 -ylidene)-malononitrile (86 mg, 0.440 mmol) in anhydrous chlorofornn (8 cm3). The resulting solution was then degassed for a further 30 minutes. The ice bath was removed and the reaction mixture warmed to 23 C and stirred for 18 hours. The reaction mixture was diluted with acetonitrile (150 cm3) and stirred for 1 hour. The solid collected by filtration and washed with acetonitrile (100 cm3) and methanol (100 cm3). The crude was then purified by column chromatography (dichloromethane) followed by trituration in acetonitrile (100 cm3) to give compound 1 1 (183 mg, 97%) as a dark green solid. 1H- NMR (400 MHz, CD2CI2) 0.67 – 0.80 (24H, m), 1.1 1 – 1.23 (48H, m), 1.36 – 1.55 (16H, m), 2.43 (16H, t, J 7.7), 6.78 – 6.92 (12H, m), 7.63 – 7.74 (4H, m), 7.78 – 7.87 (4H, m), 8.60 (2H, d, J 7.3), 8.80 (2H, s).

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-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
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Synthetic Route of 7153-22-2,Some common heterocyclic compound, 7153-22-2, name is Ethyl 4-cyanobenzoate, molecular formula is C10H9NO2, 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: To a solution of hydroxylammonium chloride (1 eq.) in absolute ethanol (0.75 M) triethylamine (1 eq.) and starting compound (21 or 22) were added. The resulting solution was stirred at 60 C for 15 h. The solvent was removed under reduced pressure and residue dissolved in EtOAc, which was further washed with saturated solution of NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to give product 23 or 24.

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

Reference:
Article; Trstenjak, Uro?; Ila?, Janez; Kikelj, Danijel; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 302 – 313;,
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6330-25-2, name is 2-Cyano-N-methyl-acetamide, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-Cyano-N-methyl-acetamide

General procedure: 4-Amino-7-X-8-bromo-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).To a solution of 2-[(3-X-2-bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (1.0 equiv) in anhydrous toluene (0.1 M, 1 volume) was added aluminum chloride (3.0 equiv). The reaction was heated with vigorous stirring at 70-90 C for 1-3 h, cooled, and quenched with Rochelle’s salt (saturated aqueous potassium sodium tartrate, 0.5 volume). Afterward, the mixture was stirred at room temperature overnight. The aqueous layer was separated, and the organic layer was treated with fresh Rochelle’ salt (0.5 volume) while stirring at room temperature for 1 h. After separating the resulting layers, the organic suspension was washed with water and filtered to give give a tan solid. Additionally, the organic filtrate was concentrated, and triturated with ether to give a tan precipitate. The resulting solids were filtered to give a tan solid in 30-70% yield of crude product. The combined tan solid was dried at 50 C under high-vacuum to give the title compound, which was used without further purification.The intermediate compounds were prepared as follows:2-[(3-X-2-Bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (X = H or F).Solution A: To a mechanically stirred solution of 3-X-2-bromoaniline (1.0 equiv) in acetic acid (2 M, 1 volume) was added water (0.6 volume) at ambient temperature. The mixture was cooled to 0 C, and then concentrated aqueous HCl (0.5 volume) added. A precipitate was formed immediately and the suspension was stirred at 0 C for 20 min. To this suspension was added dropwise a solution of sodium nitrite (1.10 equiv) in water (0.6 volume), maintaining the internal temperature below 5 C. The resulting clear orange solution was stirred at 0 C for another 30 min.Solution B: To a mechanically stirred solution of N-(alkyl)-2-cyanoacetamide (1.25 equiv) in ethanol (4.5 volume) was added a solution of sodium acetate (1.60 equiv) in water (120 volume), and chilled to between 0 C and -5 C.Solution A was poured into solution B, maintaining the internal temperature below 0 C. An orange precipitate was formed gradually. The mixture was stirred below 0 C overnight, and then the orange precipitate was collected by filtration, washed with water (100 mL ¡Á 3), and dried at 50 C under high vacuum to remove water. An orange solid was obtained in greater than 95% yield, which was the ‘E’, and used for the next step without further purification.

The synthetic route of 6330-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
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Adding a certain compound to certain chemical reactions, such as: 2042-37-7, name is 2-Bromobenzonitrile, 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 2042-37-7, category: nitriles-buliding-blocks

General procedure: In an undivided cellequipped with a Zn sacrificial anode (1.5 x 1.0 cm2) and a Pt cathode (1.5 x 1.0 cm2) was placed a DMF(3 mL) solution of 4-bromopropiophenone (4a, 0.053 g, 0.25 mmol), 1 (0.14 g, 7.6 x 10-2 mmol),[Bu4N+][Tf2N-] (0.16 g, 0.30 mmol), and a catalytic amount of PdCl2(PPh3)2 (0.0086 g, 1.2 x 10-2 mmol).The solution was electrolyzed under constant current conditions (10 mA) at 60 C until 2 F/mol-4a ofelectricity was passed. The reaction mixture was poured into 5% aq. HCl (12 mL). The mixture wasextracted with AcOEt (10 mL x 3). The combined organic layer was washed successively with waterand brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified bycolumn chromatography (SiO2, toluene/AcOEt = 10/1) to afford 4,4?-dipropanoylbiphenyl (5a, 0.030 g,0.11 mmol, 89%).

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:
Article; Kuroboshi, Manabu; Kojima, Atsuki; Tanaka, Hideo; Heterocycles; vol. 94; 11; (2017); p. 2132 – 2140;,
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Reference of 114897-91-5, These common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, 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-(4-bromo-2-fluorophenyl)acetonitrile (397 g, 1.82 mol) in MeOH (500 mL) stirred under N2 at 20 C was added NaOH (2.22 L, 2.5M, 5.56 mol) solution in one charge. The reaction mixture was stirred at 80 C for 5 h. Then the solution wasconcentrated and neutralized with cone. HC1 to pH = 5 with stirring. Then the solution was extracted with EA (1.5 L x 2). Another two batches were prepared following the same procedure. Then the three batches were combined. The combined organic extract was washed with brine, dried over Na2504, filtered and concentrated in vacuo to give the pure 2-(4-bromo-2-fluorophenyl)acetic acid (1200 g, 92%): TLC (PE/EA = 5:1, Rf = 0.2); ?HNIVIR (400 IVIFIz, CDC13) 7.24 (br. s., 1H), 7.12 (t, J 7.9 Hz, 1H), 3.65 (s, 2H).

The synthetic route of 114897-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEUNG, Mui; CLARK, William M.; EIDAM, Hilary Schenck; LAMEY, Kimberly Anne; THOMAS, James V.; (73 pag.)WO2016/38519; (2016); A1;,
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