Category: nitriles-buliding-blocks

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. 2042-37-7 name is 2-Bromobenzonitrile, 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. 2042-37-7

General procedure: The tetrazole compounds were prepared by a modified literature reported protocol.3 Thus, the aromatic nitrile (1.0 equiv), TBAF.3H2O (0.5 equiv) and TMS-N3 (1.5 equiv) were taken in a screw capped vial equipped with a magnetic stirrer and the resulting mixture was stirred vigorously at 85 oC. The reaction mixture was then transferred to a seperatory funnel and TBAF was removed by washing the organic phase with 1M aqueous HCl solution (20 ml). The organic phase was separated, washed with brine (20 ml) and dried over Na2SO4 and then concentrated in a rotary evaporator. The products were then purified by silica-gel (60-120 mesh) column chromatography or for some cases by recystallisation. Compound 2L was used as a crude mixture for further reaction. The compounds were then characterized by IR, NMR spectroscopy and mass spectrometry. Compounds 2A-B and 2H are reported compounds3 whereas 2C- 2G and 2I- 2L are new.

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

Reference:
Article; Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2044 – 2050;,
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A common compound: 31643-49-9, name is 4-Nitrophthalonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 31643-49-9

General procedure: 4-nitrophthalonitrile (0.38 g, 1.92 mmol), 2,4,6-trimethylphenylamine (0.55 g, 1.92 mmol) and anhydrous DMF(15 mL) were added to a round bottom flask under a nitrogen atmosphere.A fine powder of anhydrous potassium carbonate (0.8 g,5.76 mmol) was added to this mixture. The resulting mixture was stirredat room temperature for 24 h. The crude product was collected by filtration,washedwith distilled water, and then recrystallized. The crude productwas recrystallized from THF-petroleum ether to afford a whitepowder.

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, 31643-49-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Medyouni, Rawdha; Elgabsi, Wissal; Naouali, Olfa; Romerosa, Antonio; Sulaiman Alayed, Abdullah; Baklouti, Lasaad; Hamdi, Naceur; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 167; (2016); p. 165 – 174;,
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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. 327056-73-5, name is 3-Chloro-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., 327056-73-5

To a solution of 3-chloro-5-fluorobenzonitrile (E-1, 10 g, 64.28 mmol) and 6-chloro-2-fluoro-3-methyl-phenol (E-2, 9.38 g, 58.44 mmol) in DMA (100 mL) was added Cs2CO3 (1.9 g, 5.84 mmol) followed by K2CO3 (8.9 g, 64.28 mmol). The mixture was heated to 120 C. (oil bath) under argon for 5.5 h. The reaction was cooled to RT and water (150 mL) was added. The mixture was extracted with EtOAc (150 mL) and the aqueous phase back extracted with EtOAc (2¡Á100 mL). The combined EtOAc extracts were dried (MgSO4), filtered and concentrated in vacuo afford 11.1 g (75% purity) of E-3a as a white crystalline solid.

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; Roche Palo Alto LLC; US2009/12034; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

40497-11-8, 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. 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, This compound has unique chemical properties. The synthetic route is as follows.

0.01 mol of 2-fluoroaniline and a small amount of ethanol were placed in a 250 mL round bottom three-necked flask, and 3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise with stirring under ice bath. 0.018 mol of sodium nitrite was dissolved in 10 mL of water, and slowly dropped into the flask. After the completion of the dropwise addition, the reaction was carried out for 0.5 h to obtain a yellow diazonium salt solution.Add 0.01 mol of ethyl 2,3-dicyanopropionate to a three-necked flask.The prepared diazonium salt solution was dropped into the flask, and the reaction was added dropwise for 2 hours. Ammonia water was added, the pH was adjusted to 9-10, and the reaction was carried out for 2 h at room temperature. After completion of the reaction, the mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2¡Á30 mL), and washed with saturated sodium chloride solution (1¡Á40 mL), dried over anhydrous magnesium sulfate, and then evaporated. Yield 62.3%, product melting point: 196-198 C.

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; Nanjing Tech University; Wan Rong; Chen Fuli; Han Zhenyu; Fu Xiaohuan; Jiang Peng; (17 pag.)CN108203450; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

103146-25-4, Name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 103146-25-4, 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.

50 gm of 5-Cyano phthalide was stirred in 150 ml of THF at -5C. 227 gm of l-(4-fluorophenyl) magnesium bromide was added to the above solution and stirred for about 15 minutes at -5 0C. 324 gm of l-[3- (dimethylamino) propyl] magnesium chloride was added slowly to the reaction mass at -5 0C and then stirred for about 30 minutes at room temperature. The reaction mixture was quenched into cold water (650 ml). Reaction mixture pH was adjusted to about 2 with 36% aqueous HCl (94 ml) and washed the reaction mixture with toluene (2 X 150 ml). The aqueous layer was separated, toluene (300 ml) was added and pH was adjusted to about 7.5 with aqueous ammonia (45 ml). The organic layer was separated and aqueous layer was extracted with toluene (1 X 200 ml; IX 100 ml). Total organic layer was washed with water (1 X 250 ml) followed by salt solution (1 X 250 ml). The final organic layer was distilled completely under vacuum to get 76 gm of residue.The residue obtained above was charged in 150 ml of toluene, stirred at room temperature for about 1 hour. The solution was cooled to 10-150C and stirred for about 1 hour. The solid was filtered and washed with toluene. The wet solid was dried to get 55 gm of the title compound as crystalline Form S.The obtained product was analyzed by DSC and XRD, the results are as provided in Fig. 1 & 2 respectively.

Statistics shows that 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 103146-25-4.

Reference:
Patent; SHODHANA LABORATORIES LIMITED; GIRIDHAR, Thota; SRINIVASULU, Gudipati; SRINIVASA RAO, Kotaru; WO2010/4575; (2010); A2;,
Nitrile – Wikipedia,
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939-80-0, name is 4-Chloro-3-nitrobenzonitrile, 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. 939-80-0

Example 224 Preparation of 6-L-CYCLOHEXYL-5- (1H-TETRAZOL-5-YL)-1H-BENZIMIDAZOL-2-VLL-2- PHENYLQUINOXALINE (Compound 258) Step 1: 4-CYCLOHEXYLAMINO-3-NITROBENZONITRILE (Compound 127); [0776] A solution of 1 g (5.48 mmol) 4-CHLORO-3-NITROBENZONITRILE, Compound 126, and 1.14 g (11. 51 mmol) of cyclohexylamine were heated overnight in 5 mL anhydrous DMF. After cooling to room temperature, the solution was added dropwise into 100 mL H20 stirring vigorously. The solids were collected by filtration and dried under vacuum yielding 1.34 g (100%) bright yellow solids which were used as such without analysis in the next step.

Statistics shows that 939-80-0 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitrobenzonitrile.

Reference:
Patent; GENELABS TECHNOLOGIES, INC; WO2005/12288; (2005); A1;,
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17216-62-5, 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, A new synthetic method of this compound is introduced below.

EXAMPLE 9 1,4,8,11-Tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane, 8 Diethyl 2-(2-cyanoethyl)malonate 7 (5.0 g, 23.5 mmole–Aldrich Chemical Company) was added dropwise over a one hour period to a stirred portion of freshly distilled ethylene diamine (15 g, 0.25 mole) which was maintained under nitrogen at O C. The stirred solution was allowed to warm to room temperature (25 C.) and stirring was continued over a four day period. At this point, the excess ethylene diamine was removed in vacuo with care to avoid heating over 40 C. The crude clear oil which resulted was subjected to flash chromatography using Solvent System 3 as the eluent to give 2.3 g (8.81 mmole) of 1,4,8,11-tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane as a clear viscous oil in 37 percent yield (Rf =0.39/Solvent System 3): 1 H NMR (CDCl3) delta 7.59 (t, 2H, amide H), 3.29 (m, 5H, methine H and alpha-amido CH2), 2.82 (dt, 4H), beta-amido CH2) 2.48 (t, 2H, alpha-nitrile CH2) 2.21 (q, 2H, beta-nitrile CH2),1.39 (s, 4H, amino NH); 13 C NMR (CDCl3) delta 169.6 (amide carbonyl), 118.9 (nitrile), 52.9, 42.3, 41.2, 27.1, 15.4.

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; The Dow Chemical Company; US5489425; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 591769-05-0 as follows. 591769-05-0

To a solution of 4-iodo-lH-pyrazole 34e (0.72 g, 3.75 mmol) in acetonitrile (10 mL) was added 3-cyclopentylacrylonitrile 34c (0.5 g, 4.12 mmol) and DBU (0.57 g, 3.75 mmol). The reaction mixture was stirred at room temperature and concentrated in vacuum. The residue obtained was dissolved in ethyl acetate washed with 1 N aqueous HC1, brine, dried and concentrated in vacuum to furnish crude as oil. The crude was purified by flash column chromatography (silica gel 24 g, eluting with 0-50percent ethyl acetate in hexane) to furnish 3- cyclopentyl-3-(4-iodo-lH-pyrazol-l-yl)propanenitrile 34f (0.845 g, 72percent) as a colorless oil;1HNMR (300 MHz, DMSO) delta 8.06 (d, J= 0.6, 1H), 7.61 (s, 1H), 4.40 (td, J= 5.2, 9.0, 1H), 3.20 – 3.04 (m, 2H), 2.39 – 2.21 (m, 1H), 1.74 (m, 1H), 1.63 – 1.36 (m, 4H), 1.33 – 1.18 (m, 2H), 1.13 – 1.02 (m, 1H).

According to the analysis of related databases, 591769-05-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KOTIAN, Pravin L.; KUMAR, V. Satish; WU, Minwan; LIN, Tsu-Hsing; WO2011/31554; (2011); A2;,
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A common compound: 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 610-66-2

General procedure: A mixture of aromaticaldehyde 1 (10 mmol), active methylene compound2 (10 mmol), and nano-ZnO catalyst (5 mol %) inaqueous ethanol (10 mL) was stirred under refl ux. Theformation of the products was monitored by TLC. Aftercompletion of the reaction (by TLC), the mixture wascooled to room temperature and fi ltered. The fi ltratewas concentrated to obtain a crude product, which waspurifi ed by recrystallization from aqueous ethanol.

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, 610-66-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alam, M. M.; Asiri, Ya. I.; Sulthana, S. Sh.; Tasqeeruddin, S.; Russian Journal of Organic Chemistry; vol. 56; 2; (2020); p. 315 – 321;,
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Adding a certain compound to certain chemical reactions, such as: 21524-39-0, name is 2,3-Difluorobenzonitrile, 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 21524-39-0, 21524-39-0

Example 11; Step llA : Compound 11b; To a flame-dried flask, 2,3-difluorobenzonitirle (10 g, 72 mmol) was added along with dry ether (18 mL) and the mixture was allowed to stir at room temperature under nitrogen atmosphere. To the reaction flask, isopropyl Grignard reagent (72 mL, 2M in ether) was added slowly. The reaction mixture was then allowed to reflux (-40 C) for 2 hours. The reaction was then cooled to 0 C and was quenched with a mixture of water (30 mL) and 2N HC1 (60 mL). The biphasic reaction mixture stirred at 50 C for 3 hours then cooled to room temperature. The organic layer was separated and the aqueous phase was extracted with ether (2 x 75 mL). The organic phases were combined and were washed with saturated NaHC03 solution (2 x 100 mL) followed by washing with saturated NaCl solution (100 mL). The organic layer was isolated, dried over anhydrous MgS04, filtered, and evaporated to dryness in vacuo. Difluorophenyl ketone Ila, was recovered in 86% yield (11.6 g, 63 mmol) after purification by column chromatography on silica using 30% hexanes/dichloromethane as the eluent (Rf= 0. 8). Compound lla (11. 6 g, 63 mmol) was dissolved in 1,4-dioxane (63 mL) along with potassium carbonate (17. 5g, 127 mmol) and 1-boc-piperazine (11. 8 g, 63 mmol). The reaction mixture was allowed to reflux for 2 days then cooled to room temperature and filtered to remove potassium carbonate. Solvent from the mother liquor was removed under vacuum and the residue was purified by column chromatography on silica using 10% ethyl acetate/hexanes as the eluent (Rf= 0.3) to give 11b (15.8, 45 mmol, 71% yield). MS: calc. for Cl9H27FN203 : 350.2 ; Found: 351.0 (M+H); retention time: 2.24 minutes; Method info: APCI positive ion scan 100-1000 Frag V = 80; 95% 0.05% TFA/H20 to 95% ACN/0.05% TFA over 2 min, 3.4 min run, ODS-AQ column.

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-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts