Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, 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 20925-27-3, Application In Synthesis of 4-Amino-2-chlorobenzonitrile

Step 1: Synthesis of 2-chloro-4-isothiocyanatobenzonitrile (B) To a stirred solution of 4-amino-2-chlorobenzonitrile (A, 1 g, 6.55 mmol) in dichloromethane (9 mL) was added sodium bicarbonate (2.21 g, 26.31 mmol) and water (9 mL). The resulting mixture was cooled to 0 C., to which thiophosgene (817 mg, 7.11 mmol) was added in drop wise in 30 min at 0 C. The resulting mixture was then warmed up to room temperature and stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane (200 mL), washed with brine (50 mL*2), dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give a crude residue. The residue was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v=1:30)) to give desired product (yield: 71%)1HNMR (400 MHz, CDCl3): delta 7.69 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.28 (m, 1H);

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; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 16532-79-9, name is 4-Bromophenylacetonitrile, 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 16532-79-9, COA of Formula: C8H6BrN

4-bromophenylacetonitrile (23.0 g, 117 mmol) and iodine (29.8 g, 117 mmol) were dissolved in 400 ml of ether,Lower the temperature to -78 C. Sodium methoxide (13.3 g, 246 mmol) dissolved in anhydrous methanol at a concentration of 10 wt% is slowly dropped, the temperature is raised to 0 C, and the mixture is stirred for 4 hours. After the reaction was completed by adding 5% HCl (Hydrochloric acid) aqueous solution, the mixture was filtered, washed with water and cold methanol, and then recrystallized from chloroform and methanol to obtain a white solid .

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromophenylacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; LG Chemical Co., Ltd; Kim, Jin Suk; Choi, Chung-min; Bae, Jae-Sung; Lee, jae cheol; Lee, Ji Young; Jo, Geun; (30 pag.)KR101595147; (2016); B1;,
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 34916-10-4 as follows. Formula: C7H9NO

Example 77 Ethyl 2-(4-cyanocyclohexylidene)acetate; [0411] To a dispersion of sodium hydride (132 mg, 5.51 mmol) in THF (15 mL), triethyl phosphonoacetate (1.10 mL, 5.51 mmol) was added dropwise. The mixture was stirred until it was colorless before 4-oxocyclohexanecarbonitrile (Astrazeneca AB, see WO2007/13848 Al , 2007)(617 mg, 5.01 mmol) was added. The solution was stirred at ambient temperature until the reaction was complete (TLC). The reaction was quenched by the addition of saturated aqueous NH4CI and the aqueous layer was extracted with ethyl acetate (2 x 40 mL). The combined organic extracts were washed with brine, dried and concentrated. The crude product was used directly in the next step.

According to the analysis of related databases, 34916-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEWLINK GENETICS; MAUTINO, Mario, R.; KUMAR, Sanjeev; JAIPURI, Firoz; WALDO, Jesse; KESHARWANI, Tanay; ZHANG, Xiaoxia; WO2011/56652; (2011); A1;,
Nitrile – Wikipedia,
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Related Products of 4592-94-3, These common heterocyclic compound, 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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: To the 1 mol eq. of 3-aryl-3-oxopropanonitrile (2) was added1 mol eq. of hydrazine hydrate (1) in Toluene/EtOH (9:1) and thereaction mixture was refluxed for 30 min then another 1 mol eq. ofdifferent 3-aryl-3-oxopropanonitrile (2) and catalytic amount ofPTSA (0.01 mol eq.) was added. Again reaction mixture wasrefluxed up to 4 h. On completion of the reaction, excess solvent was distilled off. The solid so obtained was filtered and washedwith cold ethanol. Solid was neutralised with aq. sodium bicarbonatesolution and again filtered. Compound thus obtained wasair dried and recrystallized from ethanol.

The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aggarwal, Ranjana; Singh, Gulshan; Kaushik, Pawan; Kaushik, Dhirender; Paliwal, Deepika; Kumar, Ajay; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 326 – 333;,
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Synthetic Route of 796600-15-2, 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 796600-15-2 as follows.

Example 1; 2-chloro-4-((1R,2S)-2-hydroxy-1-(5-phenyl-1,3,4-oxadiazol-2-yl)propylamino)-3-methylbenzonitrile; Intermediate 1a; (2R,3S)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid; 2-chloro-4-fluoro-3-methylbenzonitrile (CAS 796600-15-2, 45g, 265.4 mmol) was mixed together with H-D-Thr-OH (37.92 g, 318.4 mmol) in DMSO (250 mL). K2CO3 (73.35 g, 530.7 mmol) was added to the reaction mixture and the reaction mixture 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 on silica gel with a gradient of hexanes/EtOAc and then with EtOAc, 100% to get the purified final product (39.0 g, 54%) 1H NMR (500 MHz, Acetone-d6, delta in ppm) 7.49 (d, J=9 Hz, 1H), 6.70 (d, J=9 Hz, 1H), 5.38 (d, J=10 Hz, 1H), 4.47 (d, J=6 Hz, 1H), 4.25 (m, 1H), 2.34 (s, 3H), 1.33 (d, J=6 Hz, 3H).

According to the analysis of related databases, 796600-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Miller, Chris P.; US2009/253758; (2009); A1;,
Nitrile – Wikipedia,
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Application of 40497-11-8, A common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

Add 0.01 mol of 3-bromoaniline and a small amount of ethanol to a 250 mL round bottom three-necked flask.Under ice bath, 3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise with stirring.Dissolve 0.018 mol of sodium nitrite in 10 mL of water and slowly drip 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, and the organic layer was washed with water (2¡Á30 mL), and washed with a saturated sodium chloride solution (1¡Á40 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. Yield 70.1%,

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Tech University; Wan Rong; Chen Fuli; Han Zhenyu; Fu Xiaohuan; Jiang Peng; (17 pag.)CN108203450; (2018); A;,
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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. 6609-56-9, name is 2-Methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Methoxybenzonitrile

Example 34 5-Bromo-2-(methyloxy)benzonitrile Br2 (13.7 g, 86.0 mmol) in CHCl3 (20 mL) was added to a solution of 2-(methyloxy)benzonitrile (10.9 g, 81.9 mmol) in CHCl3 (50 mL). The mixture was refluxed for 29 h. The reaction was allowed to cool to room temperature, and washed with saturated sodium bisulfite (50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 5-bromo-2-(methyloxy)benzonitrile (12.4 g, 71percent).

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 6609-56-9.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 621-03-4, 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. 621-03-4, name is 2-Cyano-N-phenylacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 0.87 g t-BuOK (7.8 mmol) in 10 cm3 drymethanol, 2-cyanoacetamide 2a-2g (2.9 mmol) was added.The reaction mixture was stirred for 10-15 min, followed by cooling to 0 C and adding a solution of o-(azidomethyl)benzoate 1a-1c (2.6 mmol) in 5 cm3 drymethanol. After heating the reaction mixture back to room temperature, it was stirred under TLC monitoring for36-48 h and evaporated. Water (15 cm3) was added to the residue and it was acidified with HCl to pH 4-5. The resulting precipitate was filtered off and recrystallized from acetic acid.

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-Cyano-N-phenylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yakovenko, Georgiy G.; Yagodkina, Marta S.; Bol?but, Andriy V.; Shishkina, Svitlana V.; Vovk, Mykhailo V.; Monatshefte fur Chemie; vol. 148; 6; (2017); p. 1035 – 1041;,
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Related Products of 1835-65-0,Some common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, 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.

Toamixtureof5mmol of tetrafluorophthalonitrile (1.2 g,5mmol) and5mmol of 4-Methoxy-1-naphthol (0.87 g, 5 mmol) in 50 ml of DMSO at ambient temperature was added 5 mmolof lithium hydroxide monohydrate (0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for24 h at same temperature and then it was poured to 100ml of water. Then extracted with chloroform(2 ¡Á 100 mL), washed with water (1 ¡Á 100 mL) and brine (1 ¡Á 100 mL) solution anddried over Na2SO4. The solvent was removed under reduced pressure. The resulting residuewas purified by silica-gel column chromatography using Benzene:Hexane (8:2) as an eluent toobtain compound 3 (1.41 g, 80.1percent) as a yellow solid. 1H NMR (600MHz, CDCl3 ppm) delta 7.94(d, J = 8.2 Hz, 1H), 7.43 (d, J = 8.2 Hz, 1H), 7.30-7.26 (m, 1H), 7.19-7.15 (m, 1H), 6.45 (d,J = 8.3 Hz, 1H), 6.36 (d, J = 8.3 Hz, 1H). 13C NMR (125 MHz, CDCl3, ppm) delta 155.7, 153.9,152.6, 146.1, 143.5, 128.5, 127.4, 126.7, 126.2, 125.4, 122.6, 122.0, 121.1, 120.6, 109.8, 109.1,102.2, 101.9, 55.8. IR (KBr tablet) numax/cm?1: 3010, 2940, 2236, 1633, 1597, 1386, 1289, 1152,1042, 978, 760. MALDI-TOF-MS: m/z calcd for C19H9F3N2O2, 354; found 355 [M + H+]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrafluorophthalonitrile, its application will become more common.

Reference:
Article; Jeong, Jaemyeng; Kumar, Rangaraju Satish; Kim, Ick Jin; Son, Young-A; Molecular Crystals and Liquid Crystals; vol. 644; 1; (2017); p. 249 – 256;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (S)-2-((ieri-butoxycarbonyl)amino)-3-(3-chloro-4-(trifluoromethoxy)- phenyl)propanoic acid (example la; 3.52 g, 9.17 mmol, Eq: 1) in DMF (40 ml) 1- aminocyclopropanecarbonitrile hydrochloride (1.31 g, 11 mmol, Eq: 1.2), HATU (6.98 g, 18.3 mmol, Eq: 2) and /Pr2Net (4.15 g, 5.61 ml, 32.1 mmol, Eq: 3.5) were added at 0 C under an Argon atmosphere. The mixture was stirred for 3h, during that time to the mixture was warmed up to 25 C. After that the mixture was diluted with EtOAc. The organic phase was extracted with water (2x) and brine (3x), dried over Na2S04, filtered, and evaporated to dryness. The mixture was purified by flash chromatography (Si02; CH2Cl2/EtOAc, gradient from 100:0 to 0: 100 within 40 min) to yield the title compound (3.14 g; 76.4%) as a yellow solid. MS (ESI): m/z = 446.1 [M-H] .

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GIROUD, Maude; HAAP, Wolfgang; KUHN, Bernd; MARTIN, Rainer E.; (75 pag.)WO2017/89389; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts