Category: nitriles-buliding-blocks

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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., 326-62-5

General procedure: To a solution of 11a-c (10 mmol) in anhydrous DMF (15 mL) was added appropriate aryl acetonitriles (12 mmol). After stirring at -10C for about 15 min, 60% NaH (0.48 g, 12 mmol) was added portion wise under a nitrogen atmosphere and maintained at this condition for 1 h. Then, the resulting mixture was warmed slowly to room temperature and continued to react for 12-24 h. After that, additional NaH (0.48 g, 12 mmol) was added and the air was introduced, the mixture was stirred at room temperature for another 12-24 h to yield 13a-q. Without further purification, 13a-q were hydrolyzed with 30% aqueous sodium hydroxide at room temperature for 4 h, and afterwards, the mixture was poured into 300 ml H2O and neutralized with 3N HCl. The precipitate was collected and purified by column chromatography on silica gel (hexane: EtOAc=8:1-1:1) to afford the target compounds 7a-q.

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; Wu, Hai-Qiu; Yan, Zi-Hong; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6477 – 6483;,
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78473-00-4, A common compound: 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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.

3,5-Dichloro-4-isothiocyanatobenzonitrile To a cooled (0 C.) solution of 4-amino-3,5-dichlorobenzonitrile (1 equiv.) in anhydrous DCM (0.5 M) was added DIEA (3 equiv.) in one portion. SCCl2 (3 equiv.) was added dropwise over 20 min. After the addition, the reaction mixture was stirred for about 5 h at 0 C. The solvent was evaporated to give a brown solid, which was purified by column chromatography on silica gel (petroleum/ethyl acetate=25/1) to give 3,5-dichloro-4-isothiocyanatobenzonitrile as a light yellow solid (75%).

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, 4-Amino-3,5-dichlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); A1;,
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876-31-3, A common compound: 876-31-3, name is 4-(Cyanomethyl)benzonitrile, 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.

General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

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, 4-(Cyanomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Yajun; Jin, Weiwei; Liu, Chenjiang; Molecules; vol. 24; 21; (2019);,
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52133-67-2, The chemical industry reduces the impact on the environment during synthesis 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, I believe this compound will play a more active role in future production and life.

The synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-cyano-4,4-diethoxybutyrate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (91 pag.)WO2016/22890; (2016); A1;,
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876-31-3, The chemical industry reduces the impact on the environment during synthesis 876-31-3, name is 4-(Cyanomethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: The general procedure for the synthesis and characterization of 1,1?-ferrocenyl-diacrylonitriles is displayed in Scheme 1 and has been previously reported [20]. In brief, 1,1?-ferrocenedicarboxaldehyde and substituted phenylacetonitriles (2.2 Eq.) were mixed in a Pyrex tube fitted with a ground glass joint. The compounds were thoroughly ground in the open air with a glass rod in the presence of 1-2 drops of piperidine to form a melt. The melt was first dried in open air, followed by drying under a vacuum line. The dry products were purified by means of silica gel chromatography. Formation of the products was determined by use of IR or NMR spectroscopy (1H- and 13C-NMR). In the solid-state IR spectra, the formation of the products was characterized by the disappearance of the sharp carbonyl absorption band at approximately 1650cm-1 and the appearance of a strong nitrile absorption band at approximately 2200cm-1. The 1H- and 13C-NMR spectra showed the disappearance of the carbonyl resonance (?10ppm) and the appearance of alkene resonance peaks (?7.4ppm). Pure compounds were further analyzed by melting point determination (DSC), mass spectrometry, microanalysis, and X-ray diffraction. 4.2.1 1,1?-Ferrocenyldi[-2(4-cyanophenyl)acrylonitrile] (para-CN catalyst) The general procedure for the synthesis of this catalyst is described in Section 4.2 and involves the use of 1,1?-ferrocenyldicarboxaldehyde (145.0 mg, 0.60 mmol) and 4-cyanophenylacetonitrile (188.0 mg, 1.32 mmol). Upon grinding, a deep maroon paste was formed which was dried to obtain a maroon solid. Reaction completion was monitored by use of preparative TLC plates with a solvent system of hexane/diethyl ether (1:1). The final product was then purified by means of column chromatography with a solvent system of hexane/diethyl ether (1:1) to obtain dark maroon crystals (219.0 mg, 74%) as the desired product and 37.0 mg of the recovered starting (1,1?-ferrocenedicarboxaldehyde). Product d.p. ca. 325 C; IR (cm-1) 3182, 2926, 2852, 2213, 1608, 1587, 1510, 1452, 1417, 1371, 1319, 1251, 1180, 1035, 996, 918, 830, 819, 542, 501, 486, 456, 425; 1H-NMR spectra (CDCl3) 7.55 (4H, d, J 8.4 Hz, ArH), 7.47 (4H, d, J 8.5 Hz, ArH), 7.34 (2H, s, CH), 5.08 (4H, s, C5H4), 4.65 (4H, s, C5H4); 13C-NMR spectra (CDCl3) 132.7, 125.3, 77.2, 73.7, 72.2; HR-MS (C30H18FeN4) ES: [M + H+] m/z calc. 491.0959, found 491.0969.

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

Reference:
Article; Ombaka; Ndungu; Omondi; McGettrick; Davies; Nyamori; Journal of Solid State Chemistry; vol. 235; (2016); p. 202 – 211;,
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1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Part C. tert-butyl (7bR,11aS)-6-[4-cyano-2-(trifluoromethyl)phenyl]-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate. To a solution of tert-butyl (7bR,11aS)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate (0.135 g, 0.28 mmol) in 15 mL of DMF and 2 mL of water was added 4-bromo-3-(trifluoromethyl)benzonitrile (0.143 g, 0.57 mmol) and sodium carbonate (0.15 g, 0.1.43 mmol). The mixture was degassed with a stream of nitrogen for 20 min and then there was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (20 mg, 0.028 mmol) and the mixture was stirred at 80 C. for 16 h. The reaction was allowed to cool to ambient temperature and was diluted with ethyl acetate, washed with sat’d aqueous sodium bicarbonate and brine, dried (MgSO4), filtered through Celite and concentrated in vacuo to afford 130 mg (88%) of the title compound, which was used without purification. LRMS (ES+): 516.1 (M+H)+.

The synthetic route of 4-Bromo-3-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
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Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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. 3939-09-1

Potassium tert-butoxide (216 ml, 1M in tetrahydrofuran, 216 mmol) was added to ice-cooled methanol (8.7 ml, 216 mmol), and the solution stirred for 40 minutes. The resulting suspension was added dropwise to a solution of 2,4-difluorobenzonitrile (30 g, 216 mmol) in tetrahydrofuran at -78 C. Once addition was complete the reaction was allowed to warm to room temperature and stirred for 18 hours. The reaction was diluted with hexane (200 ml) and the mixture washed with water (200 ml), brine (2*200 ml), then dried (MgSO4) and evaporated under reduced pressure. The residual solid was recrystallized from ethyl acetate:hexane to give the title compound, 9.8 g. 1H-NMR (CDCl3, 300 MHz) delta: 3.90 (s, 3H), 6.70 (m, 2H), 7.55 (dd, 1H). LRMS: m/z ES+ 152 [MH+]

The chemical industry reduces the impact on the environment during synthesis 2,4-Difluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Barber, Christopher Gordon; Bunnage, Mark Edward; Harvey, John Wilson; Mathias, John Paul; US2005/20611; (2005); A1;,
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Adding some certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4. 127946-77-4

Into a 25-mL round-bottom flask, were placed (1R,2R)-2-(2-(5-chloropyridin-3-yl)-5-(4- (1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-4,4-difluorocyclohexanecarboxylic acid (10.0 mg, 0.018 mmol, 1.00 equiv), 1-aminocyclopropanecarbonitrile hydrochloride (12.0 mg, 0.101 mmol, 5.74 equiv), HATU (16.0 mg, 0.042 mmol, 2.39 equiv), DIPEA (26.0 mg, 0.20 1 mmol, 11.4 equiv) and DMF (1.5 mL). The resulting mixture was stirred for 16 h at ambienttemperature and diluted with ethyl acetate (5.0 mL). The resulting mixture was washed with brine (5.0 mL). The aqueous layer was extracted with ethyl acetate (3 x 10.0 mL). The combined organic layers were washed with brine (3 x 10.0 mL), dried (Na2504), filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1:1). This resulted in 3.00mg (27%) of(1R,2R)-2-(2-(5-chloropyridin-3 -yl)-5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-N-( 1- cyanocyclopropyl)-4,4-difluorocyclohexanecarboxamide (Compound 2) as a light yellow solid:?H NMR (300 MHz, CDC13) Sppm 9.12 (s, 1H), 8.63 (s, 1H), 8.27 (s, 1H), 7.44 (d, J 9.0 Hz, 2H), 7.02 (d, J= 9.0 Hz, 2H), 5.92 (brs, 1H), 4.08-3.90 (m, 4H), 3.62-3.45 (m, 1H), 3.22-3.11 (m, 4H), 2.91-2.78 (m, 1H), 2.35-2.18 (m, 3H), 2.13-1.91 (m, 3H), 1.48-1.21 (m, 2H), 0.92-0.83(m, 2H); MS (ES, m/z): 632.1 (M + 1), 634.1 (M + 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 1-Amino-1-cyclopropanecarbonitrile hydrochloride.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
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6393-40-4, 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. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
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Adding some certain compound to certain chemical reactions, such as: 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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 1483-54-1. 1483-54-1

General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

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 2-Amino-4-(trifluoromethyl)benzonitrile.

Reference:
Article; Sun, Yajun; Jin, Weiwei; Liu, Chenjiang; Molecules; vol. 24; 21; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts