Month: August 2021

Electric Literature of 621-03-4, 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. 621-03-4 name is 2-Cyano-N-phenylacetamide, 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.

General procedure: Under N2 atmosphere, t-BuOK (246 mg, 2.2 mmol) and various acetamides 2 (1.0 mmol) in dry THF (5 mL) were placed in a 10 mL Schlenk flask at -78 C. The suspension was warmed to room temperature for 30 min and recooled to -78 C. (Z)-methyl-bromo-4,4,4-trifluorobut-2-enoate 1 (117 mg, 0.5 mmol) was added at this temperature. The solution was stirred at this temperature until the reaction was completed (usually 15-30 min), followed by adding saturated aqueous NH4Cl solution (10 mL). The solution mixture was extracted with EtOAc (3×10 mL), and the combined organic layer was washed with brine, then, dried over Na2SO4. After removal of solvents under vacuum, the crude product was further purified by silica gel column chromatography (PE:EA = 1:2 v/v) to afford pure product 4.

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

Reference:
Article; Zhang, Hong-Hai; Shen, Wei; Lu, Long; Tetrahedron Letters; vol. 59; 11; (2018); p. 1042 – 1045;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 796600-15-2

Example 38; DL-Threo-2-chloro-4-(2-hydroxy-2-phenyl-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethylamino)-3-methylbenzonitrile; Intermediate 38a; DL-Threo-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxy-3-phenylpropanoic acid; 2-chloro-4-fluoro-3-methylbenzonitrile (2.0 g, 11.79 mmol) was mixed together with DL-Threo-3-phenylserine hydrate (2.82 g, 14.15 mmol) in DMSO (15 mL). K2CO3 (3.26 g) was added to the reaction mixture and stirred at 75 C. for 24 h. The reaction mixture was cooled to room temperature and poured slowly into a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexanes/EtOAc and then with EtOAc, 100% to get the pure final product (800 mg). 1H NMR (500 MHz, acetone-d6, delta in ppm) 7.52 (m, 3H), 7.37 (d, J=9 Hz, 1H), 7.2-7.30 (m, 2H), 6.81 (d, J=9 Hz, 1H), 6.44 (d, J=6 Hz, 1H), 5.42 (m, 1H), 4.5 (br s, 1H), 4.17 (m, 1H) 2.24 (s, 3H)

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; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 151-18-8, 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. 151-18-8, name is 3-Aminopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a schlenk-type flask, corresponding aliphatic amine (2 mmol) and intermediates Y-5 (0. 5 mmol) were dissolved in dry dioxane (5 mL), and then Pd2(dba)3 (0.05 mmol), XantPhos (0.05 mmol) and Cs2CO3 (7.5 mmol) were added. The mixture was refluxed to 105 C while stirring under nitrogen atmosphere. The reaction was followed by TLC until its completion. After cooling, the solvent was evaporated under reduce pressure. The residue was purified by flash column chromatography using ethyl acetate/petroleum ether as eluent to give target compounds Ia-Im and IIa-IIm (except Ii and Iii). For Ii and IIi, the Boc group was further removed using CF3COOH to provide the two compounds.

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

Reference:
Article; Yang, Jiapei; Chen, Wenmin; Kang, Dongwei; Lu, Xueyi; Li, Xiao; Liu, Zhaoqiang; Huang, Boshi; Daelemans, Dirk; Pannecouque, Christophe; De Clercq, Erik; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 294 – 304;,
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Application of 213598-11-9, A common heterocyclic compound, 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate, molecular formula is C12H13NO3, 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 mixture of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (27 g, 123.28 mmol) (Description 4) in methanol (150 mL) was added sodium hydroxide (5N) (27 mL, 135 mmol) and the mixture stirred at RT for 16 h. The mixture was then reduced in vacuo and acidified with hydrochloric acid (2M) (35 mL). Ethyl acetate (200 mL) was added, the layers separated and the organic layer dried over sodium sulfate and then reduced to a solid which was washed with pentane to afford the title compound (25.27 g).

The synthetic route of 213598-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Nitrile – Wikipedia,
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Electric Literature of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-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.

To a solution of 4-bromo-2-methylbenzonitrile (4.00 g, 20.4 mmol) in THF (40 mL) was added dropwise lithium diisopropylamide (2 Mm THF, 16 mL, 32 mmol) in THF (10 mL) over a period of 20 mm at -78 C under nitrogen atmosphere. After stirring 2 hr at the sametemperature, iodomethane (3.48 g, 24.5 mmol) was added dropwise over a period of 20 mm. The mixture was warmed to room temperature, stirred for 3 h, re-cooled to 0 C and acidified with 1 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-10% ethyl acetate inpetroleum ether) to afford the title compound. LCMS [M+H] = 210.

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BISWAS, Dipshikha; DING, Fa-Xiang; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; PASTERNAK, Alexander; SUZUKI, Takao; VACCA, Joseph; XU, Shouning; WO2015/103756; (2015); A1;,
Nitrile – Wikipedia,
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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. 13531-48-1, name is Methyl 3-cyanobenzoate, A new synthetic method of this compound is introduced below., Product Details of 13531-48-1

EXAMPLE 24 3-(3,4,8,9-Tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)benzoic acid methyl ester Conc. sulfuric acid (1.8 mL) was added to a solution of methyl 3-cyanobenzoate (2.42 g, 15.0 mmol) in toluene (15 mL) and acetic acid (8 mL) with cooling in ice and then a solution of 2,3-dihydro-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propenyl)benzofuran (3.49 g, 15.0 mmol) in toluene (15 mL) was added to the mixture. The mixture was stirred at 80 C for 1 hour. The reaction mixture was cooled with ice, combined with an aqueous solution containing sodium acetate (6.69 g, 81.6 mmol), and then neutralized with conc. aqueous ammonia and extracted twice with ethyl acetate. The combined organic layer was washed with water and extracted with 1 M hydrochloric acid3 times. The combined aqueous layer was neutralized with cone. aqueous ammonia and extracted twice with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to a column chromatography on a basic silica gel (hexane/ethyl acetate 10:1) and crystallized from ethyl acetate-hexane to obtain the title compound (2.18 g, Yield: 37%). Melting point: 137-138 C. 1H NMR (CDCl3) delta 1.26 (6H, s), 1.30 (6H, s), 2.16 (2H, s), 2.70 (2H, s), 3.92 (3H, s), 3.93 (3H, s), 6.63 (1H, s), 7.48 (1H, t, J = 7.8 Hz), 7.62 (1H, dt, J = 7.8, 1.5 Hz), 8.05-8.12 (2H, m).

The synthetic route of 13531-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1270577; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 455-18-5,Some common heterocyclic compound, 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, molecular formula is C8H4F3N, 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 stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).

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

Reference:
Article; Sharonova, Tatyana; Pankrat’eva, Vitalina; Savko, Polyna; Baykov, Sergey; Shetnev, Anton; Tetrahedron Letters; vol. 59; 29; (2018); p. 2824 – 2827;,
Nitrile – Wikipedia,
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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 53312-81-5 as follows. Safety of 5-Amino-2-fluorobenzonitrile

A solution of (R)-tert-butyl [1-(2-chloro-6-propylpyrimidin-4-yl)piperidin-3-yl](methyl)carbamate (50 mg, 0.14 mmol) prepared in Preparation 28 and 5-amino-2-fluorobenzonitrile (23 mg, 0.17 mmol) in n-butanol (1 ml) was refluxed under stirring overnight. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 1/1 ? dichloromethane/methanol = 10/1) and then dissolved in methanol. Hydrogen chloride gas was added to the solution. The reaction mixture was stirred at room temperature for 5 hours and then filtered to give 23 mg of the product as a pale yellow solid.

According to the analysis of related databases, 53312-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; LEE, Hyun-Joo; KIM, Dong-Hoon; KIM, Tae-Kyun; YOON, Young-Ae; SIM, Jae-Young; CHA, Myung-Hun; JUNG, Eun-Jung; AHN, Kyoung-Kyu; LEE, Tai-Au; WO2012/115478; (2012); A2;,
Nitrile – Wikipedia,
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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., Recommanded Product: 3-Oxobutanenitrile

Step 3. 2-Benzyl-3-oxobutanenitrile To a solution of Na (1.17 g, 50.87 mmol) in EtOH (20 mL) was added 3-oxobutanenitrile (2.5 g, 30.09 mmol) and (bromomethyl)benzene (5 g, 29.23 mmol), and the reaction mixture was stirred for 2 hours at 80 C. The resulting mixture was concentrated in vacuo, diluted with water (200 mL), adjusted to pH 6 with HCl (3N), extracted with ethyl acetate (3*100 mL), dried over anhydrous magnesium and concentrated in vacuo to provide a residue, which was purified via silica gel column chromatography with 1.25% to 5% ethyl acetate in petroleum ether to afford 2-benzyl-3-oxobutanenitrile as a brown solid (2 g, 39%). LC/MS (ES, m/z):[M+H]+ 174.1

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 2469-99-0.

Reference:
Patent; BIOENERGENIX; US2012/277224; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 626-17-5, A common heterocyclic compound, 626-17-5, name is 1,3-Dicyanobenzene, molecular formula is C8H4N2, 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.

Example 40 Isophthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and methanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130 C. for seven hours. The reaction mixture was cooled, and water (9 g) was added thereto. Gas chromatographic analysis revealed that methyl m-cyanobenzoate had been produced at a yield of 38% and a selectivity of 83%.

The synthetic route of 626-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts