Author: Jessica.F

935-02-4, name is 3-Phenylpropiolonitrile, 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. SDS of cas: 935-02-4

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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Reference of 64248-62-0, These common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, 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.

Thiomorpholine (4.9 mL, 48.5 mmol) and potassium carbonate (13.4 g, 96.9 mmol) was dissolved in 50 mL DMF and the 3,4-difluorobenzenenitrile (6.7 g, 48.5 mmol) was added. Reaction heated to 100C overnight. Reaction was blown to dryness and residue was taken up in EtOAc and washed with water (2x), brine and then dried over sodium sulfate. Drying agent removed by filtration and then organics concentrated down and residue was recrystallized from hot isopropanol to give 8.74 g of 3-fluoro-4- thiomorpholinobenzonitrile as a light yellow solid. Residue can also be purified through silica gel.

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLER, Marvin J.; MORASKI, Garrett; (133 pag.)WO2017/49321; (2017); A1;,
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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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 630-18-2

Preparation of the imino ester: A mixture of 8.3 g (0.1 mole) of trimethyl acetonitrile and 5.05 g of EtOH (0.11 mole) is treated with HCI gas at 5 0C until saturation. The mixture is then stored at the same temperature for 18 h and 20 ml of DEE are added. The resulting precipitate is collected by filtration, ished with DEE and dried to yield 3.9 g (24%) of the crude imino ester hydrochloride as a white solid. (1H- NMR (400 MHz, DMSO-O6): delta = 4.42 (q, 2H), 1.35 (t, 3H), 1.25 (s, 9H)).

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; NOVARTIS AG; WO2008/71404; (2008); A1;,
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17626-40-3, name is 3,4-Diaminobenzonitrile, 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. category: nitriles-buliding-blocks

General procedure: Hydroximoyl chloride 10 (0.16g, 1mmol) was added slowly by small portions to a solution of the appropriate 1,2-diaminobenzene 3 (0.3g, 1.5mmol) in ethanol (5-10mL) at room temperature. The mixture was stirred at reflux for 0.5h followed by an additional hour at room temperature, diluted with water (10mL) and 0.1M aq HCl (5mL). The heterogeneous mixture was stirred for 1h. The precipitate was filtered, washed with water, and recrystallized from iPrOH/H2O.

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stepanov, Andrei I.; Astrat’ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V.; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 237 – 251;,
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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. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Amino-4-chlorobenzonitrile

To a stiired solution of compound IM (1.0 g. 6.57 mmoi) in DMF (20 mL) under argon aimospliere was added potassium ethyl xanthate (2.6 g, 16.44 rnmol) at RT. The reaction mixture was heated to 110 C for 12 h. The progress of the reaction was monitored by TLC. The reaction mixture was acidified with IN HC1 solution (50 mL) to pH~2 to get the solid. The solid was filtered, washed wife -hexane (2 x 20 mL) and dried under reduced pressure to obtain compoimd IN (1.0 g, 5.20 rnmol, 80%) as a brown solid. NMR (400 MHz, CDC3): delta 10.03 (brs, 1H); 7.55 (s, 2H), 7.48 (s, 1H)

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 53312-79-1.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; YATES, Christopher, M.; SHAVER, Sammy, R.; HOEKSTRA, William, J.; (455 pag.)WO2017/117393; (2017); A1;,
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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. 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,3,5,6-Tetrachloroterephthalonitrile

0.60g (0.015 mol) of sodium hydroxide was added to a solution of 1.3g(0.0075 mol) of 5-bromopyridin-2-aminein 40 mL of DMF, followed by addition of 2g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring, the mixturewas stirred for 5 hours after addition at room temperature. After the reaction was over by Thin-Layer Chromatographymonitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washedwith water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reducedpressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C)= 1:3, as an eluent) to give 2.5 g of compound C-109 as yellow solid, m.p. 154-156°C.[0126] 1H-NMR (300MHz, internal standard TMS, solvent CDCl3) delta(ppm): 9.78(s, 1H, NH), 6.62(d, 1H, Py-3-1H), 7.73(dd, 1H, Py-4-1H), 8.27 (d, 1H, Py-6-1H)

According to the analysis of related databases, 1897-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinochem Corporation; Shenyang Research Institute of Chemical Industry Co., Ltd.; LIU, Changling; HUANG, Guang; LAN, Jie; HAO, Shulin; LI, Zhinian; LI, Huichao; GUAN, Aiying; JIANG, Airu; XU, Ying; EP2757092; (2014); A1;,
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Some common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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. Safety of 2,3-Dimethoxybenzonitrile

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was exuacted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5653-62-3, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5681956; (1997); A;,
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These common heterocyclic compound, 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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. category: nitriles-buliding-blocks

General procedure: To a solution of 1 (0.10 mmol, 1.0 equiv.), [(TMEDA)Ni(o-tolyl)Cl] (1.6 mg, 0.0050 mmol, 5.0 mol %),and PMePh2 (1.9 L, 0.010 mmol, 10 mol %) in THF (1.0 mL, 0.10 M) under an argon atmosphere was added Et2Zn (1.0 M in hexanes, 0.15 mL, 0.15 mmol, 1.5 equiv) at 0 C. After being stirred the mixture at 30 C for the indicated reaction time judged by TLC analysis, the electrophile (2.0 equiv) was added tothe reaction solution at 30 C unless otherwise noted. The reaction mixture was stirred at the indicated temperature for the indicated reaction time. The reaction was quenched by the addition of sat. aq. NH4Cl.The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organiclayer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified byflash column chromatography (hexane/EtOAc or hexane/CH2Cl2/EtOAc) on silica gel to afford corresponding product.

The synthetic route of Methyl (E)-2-Cyano-3-phenylacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsujihara, Tetsuya; Tomeba, Moriho; Ohkubo-Sato, Shigeaki; Iwabuchi, Kyoko; Koie, Rino; Tada, Natsumi; Tamura, Satoru; Takehara, Tsunayoshi; Suzuki, Takeyuki; Kawano, Tomikazu; Tetrahedron Letters; vol. 60; 42; (2019);,
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Electric Literature of 21803-75-8, 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 21803-75-8 as follows.

To a solution of phosgene (2.3 mL, 20% in toluene) in dry DCM (20 mL) was added a solution of 2-chloro-4-cyanoaniline (367 mg) and DIEA (372 mg) in dry DCM slowly. The resulting mixture was stirred at room temperature for 1 hr prior to evaporation to dryness. The residue was dissolved in DCM (10 mL) to which a solution of compound 1f (Example 1,510 mg) and DIEA (310 mg) in DCM was added. The resulting mixture was stirred overnight at room temperature. Aqueous sodium bicarbonate was added and the mixture was extracted with DCM. The organic phase was dried over MgS04 and evaporated to dryness.

According to the analysis of related databases, 21803-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; WO2005/63749; (2005); A1;,
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These common heterocyclic compound, 1255870-63-3, name is 4-Bromo-2-ethoxybenzonitrile, 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. Formula: C9H8BrNO

A suspension of 4-bromo-2-ethoxybenzonitrile (1.50 g, 6.5 mmol), hydroxylamine hydrochloride (913 mg, 13 mmol) and NaHCOs (1.365 g, 16.3 mmol) in water (1.32 mL) and EtOH (26.6 mL) is stirred in a sealed tube at 90 C for 3h. Once at RT, the product precipitated from the RM upon addition of water. The solid is filtered off under high vacuum, washing with water and some Et20. A first crop of pure title compound (947mg) was thus obtained as white solid. The filtrate is extracted with AcOEt. The organic layer is then washed twice with brine, dried over MgSO4, filtered and concentrated. The residue is purified by FC (hept AcOEt 5:5) to yield another crop of the pure title compound as a white solid (448 mg), merged with the first batch from precipitation. The title compound is obtained as a white solid (1.395 g, 83%). LC-MS A: tR = 0.53min, [M+H]+ = 259.03.

The synthetic route of 4-Bromo-2-ethoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (160 pag.)WO2018/210992; (2018); A1;,
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