Author: Jessica.F

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. 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrN2O2

To a stirring solution of 845 mg (3.72 mmol) of 3-bromo-5-nitrobenzonitrile in 5 rnL of THF and 5 rnL of EtOH was added 4.2 g (18.6 mmol) of SnCl22H2O in several portions.The reaction became slightly exothermic and was stirred at r.t. for about 12.5 h. The mixture was concentrated and 30 mL of 2 N NaOH was added. After the mixture was stirred for 2 h,H2O and EtOAc were added, and the organic layer was washed with 50 mL of H2O and 40 mL of brine. The aqueous layer was extracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (35% EtOAc/hexanes) provided 461 mg of 3-amino-5- bromobenzonitrile as a yellow solid in 63% yield.

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; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
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Electric Literature of 39581-21-0,Some common heterocyclic compound, 39581-21-0, name is N-Butyl-2-cyano-acetamide, molecular formula is C7H12N2O, 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: A mixture of N-alkyl-2-cyano-acetamides 1a-c (2 mmol), aldehydes 2a-f (2 mmol),malononitrile (3) (2 mmol), K2CO3 (2 mmol), and EtOH (2 mL) in a 10 mL septum-capped microwavevials was irradiated under microwave conditions at 90 C, 500 W, 200 rpm, for 10-15 min. Aftercompletion of the reaction, as indicated by TLC, each vial was de-capped and the contents were left tocool to room temperature. Then, the reaction mixture was worked up as described in method I to givecompounds 4a-q. Analytical samples were obtained by recrystallization from MeOH.

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

Reference:
Article; Mekheimer, Ramadan Ahmed; Al-Sheikh, Mariam Abdullah; Medrasi, Hanadi Yousef; Alsofyani, Najla Hosain Hassan; Molecules; vol. 23; 3; (2018);,
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These common heterocyclic compound, 766-84-7, name is 3-Chlorobenzonitrile, 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. Quality Control of 3-Chlorobenzonitrile

To a solution of 3-chlorobenzonitrile (10 g, 72.7 mmol) in 367 ml ethanol was added hydroxylammonium chloride (7.58 g, 109.0 mmol) and triethylamine (9.56 g, 94.5 mmol) and then the reaction mixture was stirred overnight at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (10.77 g, 81% of theory, 93 % purity). The compound was used without further purification. LC-MS (method 2B): RT = 1.64 min, m/z = 171 (M+H)+

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
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Some common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, molecular formula is C7BrF4N, 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. Product Details of 17823-40-4

1.14 cm3 of hydrazine monohydrate are added to 2.0 g of 4-bromo-2,3,5,6-tetrafluorobenzonitrile in 40 cm3 of absolute ethanol. The mixture is refluxed for 18 hours, 30 cm3 of distilled water are then added and the reaction medium is concentrated under reduced pressure (2 kPa; 50 C.). The residue is taken up in 100 cm3 of ethyl acetate and 10 cm3 of water, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50 C.); after drying (90 Pa; 40 C.), 2.1 g of 6-bromo-4,5,7-trifluoro-1H-indazole-3-amine are obtained in the form of a beige-coloured solid. [0959] 1H NMR spectrum (300 MHz, (CD3)2SO-d6, delta in ppm): 5.52 (s: 2H); from 12.10 to 12.90 (broad unresolved peak: 1H). [TABLE-US-00076] EI m/z = 265M+. m/z = 236[M – HN2]+ m/z = 186[M – Br]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17823-40-4, its application will become more common.

Reference:
Patent; Dutruc-Rosset, Gilles; Lesuisse, Dominique; Rooney, Thomas; Halley, Franck; US2004/14802; (2004); A1;,
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Synthetic Route of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Experiment 38. A range of experiments were conducted examining the resolution of diol with (+)- (S,S)-DTT. The general procedure is described below, and the details and results for each reaction are in table 1.Racemic diol (20 g, 58.4 mmol) was dissolved in approximately half of the solvent used for the experiment at 40 0C. (-H)-(S5S)-DTT-H2O (quantity specified in the table) was added as a solution in the other half of the solvent. The solution was held at 40 0C and was seeded within two minutes with crystals of (S)-diol. ./2(-H)-(S5S)-DTT (approximately 5 mg). Crystallisation typically began within 5-10 minutes after seeding. After 2 h at 40 0C, the temperature of the solution was lowered to 20 0C over 2 h, and the solution was held at this temperature for a further 1 h. The product was then separated by filtration, washed with the approriate solvent (2 x 20 mL) and dried overnight at 60 0C under reduced pressure.

The chemical industry reduces the impact on the environment during synthesis 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
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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 60702-69-4 as follows. Product Details of 60702-69-4

A mixture of 2-chloro-4-fluorobenzonitrile (4.26 g, 27.5 mmol), 1,1-dimethylethyl (36)-3-amino-l- pyrrolidinecarboxylate (5.11 g, 27.5 mmol) and NaHCO3 (4.62 g, 55 mmol) in 45 mL of DMSO and 5 mL OfH2O was heated with stirring at 96 0C for 6 h and 86 0C for 16 h. The reaction was diluted with 200 mL OfH2O and extracted with Et2O (3x). The extracts were washed with H2O (2x), dried over Na2SO4, filtered, and concentrated. The residue was crystallized from Et2O/hexane to

According to the analysis of related databases, 60702-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/65093; (2007); A2;,
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Synthetic Route of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of intermediate 79 (50 mg, 0.176 MMOL) in anh. DME (1 mL) were added Pd2 (dba) 3 (16 mg, 0.1 eq), 2- (dicyclohexylphosphino)-2′-methylbiphenyl (19 mg, 0.3 eq), K3PO4 (101 mg, 2.7 eq) and 4-amino-3-chlorobenzonitrile (47 mg, 1 eq). The reaction mixture was subjected to microwave irradiation (150W, 100 C, 60 psi) for 20 min. It was then quenched with sat. aq. NH4CI and extracted with EtOAc (2X10 mL). The combined organic extracts were washed with sat. aq. NaCI and dried over anh. NA2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 8: 2- 7: 3) to give the title compound as a white solid (16 mg, 22%).

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

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
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Related Products of 5922-60-1, 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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-amino-5-chlorobenzonitrile (1.00 g, 6.55 mmol) was suspended in ethyl chloroformate (3.1 mL, 33 mmol) and heated to 93 °C. The reaction was carried out for 18 h, cooled to room temperature and then worked up with a saturated solution of sodium bicarbonate and EtOAc. No further purification was required. The reaction yielded an orange solid 1.25 g, 5.56 mmol, 85percent. (Rf = 0.30, 20percent EtOAc/Hex). Mp 136-138 °C. 1H NMR (300 MHz, CDCl3) delta 8.29 – 8.22 (m, 1H, ArH), 7.59 – 7.52 (m, 2H, ArH), 7.13 (s, 1H, NH), 4.29 (q, J = 7.1 Hz, 2H, CH2), 1.36 (t, J = 7.1 Hz, 3H, CH3). 13C NMR (75 MHz, CDCl3) delta 152.68, 139.68, 134.47, 131.44, 128.14, 120.59, 117.64, 115.11, 62.27, 14.37. HRMS: calcd for C10H10N2O2Cl [M+H]+, 225.0431, found 225.0426.

The synthetic route of 2-Amino-5-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Brigg, Siobhan; Pribut, Nicole; Basson, Adriaan E.; Avgenikos, Moscos; Venter, Reinhardt; Blackie, Margaret A.; van Otterlo, Willem A.L.; Pelly, Stephen C.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 6; (2016); p. 1580 – 1584;,
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Synthetic Route of 2032-34-0, A common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, molecular formula is C7H13NO2, 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.

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

The synthetic route of 2032-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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Synthetic Route of 500912-18-5, A common heterocyclic compound, 500912-18-5, name is 2-(2-Fluoro-6-methoxyphenyl)acetonitrile, molecular formula is C9H8FNO, 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.

First, sodium bis(trimethylsilyl) amide (1.0 M tetrahydrofuran solution) (1.6 mL) was added dropwise to a solution of 2-(2-fluoro-6-methoxyphenyl)acetonitrile (86 mg) in tetrahydrofuran (2.4 mL) under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. N-benzyl-bis(2-chloroethyl)amine hydrochloride (140 mg) was added to the resultant solution, followed by reflux for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then was dried with anhydrous magnesium sulfate. the solvent was removed by evaporation under reduced pressure. The obtained residue was purified by silica gel column chromatography (diethylether/n-hexane = 50/50) to obtain 1-benzyl-4-(2-fluoro-6-methoxyphenyl)piperidine-4-carbonitr ile (132 mg). 1H-NMR (400MHz, CDCl3) delta: 2.28-2.37(m,2H),2.43-2.50(m,2H),2.50-2.59(m,2H),2.89-2.98(m ,2H),3.58(s,2H),3.91(s,3H),6.67(ddd,J=12.9,8.4,1.2Hz,1H),6. 74(d,J=8.3Hz,1H),7.21-7.29(m,3H),7.29-7.36(m,4H).

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; RIKEN; Japanese Foundation For Cancer Research; YOSHIDA, Minoru; SEIMIYA, Hiroyuki; OKUE, Masayuki; YASHIRODA, Yoko; SHIRAI, Fumiyuki; TSUMURA, Takeshi; KANO, Yuko; WASHIZUKA, Kenichi; YOSHIMOTO, Nobuko; KOUDA, Yasuko; FUKAMI, Takehiro; CHIKADA, Tsubasa; WATANABE, Takashi; (261 pag.)EP3480198; (2019); A1;,
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