Tag: M.W=200-300

Related Products of 79463-77-7, The chemical industry reduces the impact on the environment during synthesis 79463-77-7, name is Diphenyl N-cyanocarbonimidate, I believe this compound will play a more active role in future production and life.

Diphenyl N-cyanocarbonimidate [79463-77-7] (200 mg, 0.81 mmol) and 3,4-dimethoxyaniline [6315- 89-5] (137 mg, 0.89 mmol) were dissolved in DCM (2 mL) and 2-propanol (2 mL) and DIPEA (159 mg, 1.22 mmol) were added and the reaction mixture was stirred at r.t. for ~1 h. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica (gradient elution with 15 – 100% EtOAc/hexane) to afford the title compound (198 mg, 82%) as a white solid. dH (300 MHz, DMSO -d6) 10.65 (s, 1H), 7.51 – 7.37 (m, 2H), 7.36 – 7.22 (m, 3H), 7.09 (d, J 1.8 Hz, 1H), 7.03 – 6.91 (m, 2H), 3.75 (s, 6H).

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, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, Quality Control of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A mixture of 1,2-bis(bromomethyl)benzene (1.0 mmol), alpha-cyanoacetophenone (1.0 mmol) and Cs2CO3 (3.0 mmol) in DMSO (5 mL) was stirred at 80 C for 4 h till almost full conversion of the substrates by TLC analysis. The resulting mixture was dropped into 100 mL 1 M HCl (aq) and extracted with EtOAc three times (3×50 mL). The organic extract was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc=50/1) to afford the product 3aa as a white solid.

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; Wang, Jungang; Xiang, Jiachen; Wang, Miao; Guan, Jie; Wu, Anxin; Tetrahedron; vol. 70; 7; (2014); p. 1412 – 1417;,
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Related Products of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

To a solution of Mel (3.2 mL, 49.3 mmol) in anhydrous DMF (82 mL) at 0 C. was added NaH (60%, 2.0 g), followed by (4-bromo-2-fluorophenyl)acetonitrile (3.5 g, 16.4 mmol). The mixture was slowly warmed up to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated NH4Cl and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (0-20% EtOAc in hexanes) to give the product (3.0 g, 77% yield). 1H NMR (300 MHz, CDCl3) delta: 1.78 (s, 6H), 7.26-7.42 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromo-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US2005/176701; (2005); A1;,
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Related Products of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 11A 6-Chloro-2-ethylamino-3-nitro-benzonitrile A solution of ethylamine in THF (2 M, 13.8 mL, 27.6 mmol) was added slowly to a solution of 2,6-dichloro-3-nitrobenzonitrile (3.0 g, 13.8 mmol) in THF (30 mL) at -5 C. After 1.5 h, the solution was diluted with EtOAc (150 mL) and washed with 0.5 N HCl and brine. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (8:1:1 hexanes/CHCl3/EtOAc) gave 2.57 g (82%) of the title compound as an orange solid. 1H NMR (400 MHz, CDCl3): delta 8.51 (br s, 1H), 8.30 (d, 1H, J=8.8 Hz), 6.78 (d, 1H, J=8.4 Hz), 3.89-3.97 (m, 2H), 1.41 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc’d for C9H8N3O2Cl, 226, 228; found 226, 228.

The synthetic route of 2,6-Dichloro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Feng, Jun; Gwaltney, Stephen L.; Wallace, Michael B.; Zhang, Zhiyuan; US2005/272765; (2005); 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. 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C13H18N2O4

(12.2 g, 50 mmol) (E)-N,N’-bis(3-ethynylphenyl)methyl ether (Compound B) and (13.3 g, 50 mmol) 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile (Compound C3), 0.5 g of p-toluenesulfonic acid was added to 50 mL of toluene,After heating to 110 C in an oil bath for 5 h, after TLC monitoring reaction, after cooling to room temperature, concentrated, add ice water and stir for 1 h.The brown solid product erlotinib 17.34 g was obtained in a yield of 88.2%, HPLC: 99.24%.

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 950596-58-4.

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Chen Zhiyuan; Gu Huiwen; Zhang Lijie; Yang Kang; Zong Chaoyang; (11 pag.)CN108503596; (2018); A;,
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Reference of 154607-01-9,Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

1-(Benzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (0.084 g, 0.20 mmol), 4-bromo-2-chlorobenzonitrile (0.043 g, 0.20 mmol), aqueous potassium carbonate (520 muL, 1M), FibreCat 1007 (7 mg), and DMF (1 mL) were combined. The mixture was heated at 80 C. for 18 hours. After cooling, the mixture was filtered and purified by preparative HPLC to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3′-chloro-4′-cyano-6-methylbiphenyl-3-yl)cyclopropanecarboxamide.

The synthetic route of 154607-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); 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. 17354-04-0, name is 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4,5-Dimethoxy-2-nitrophenyl)acetonitrile

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

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:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Some common heterocyclic compound, 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile, molecular formula is C8H5BrFN, 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. Recommanded Product: 4-Bromo-2-fluoro-5-methylbenzonitrile

To a solution of 4-bromo-2-fluoro-5-methylbenzonitrile (10.0 g, 46.7 mmol) in N,N-dimethylacetamide (30 mL) was added Pd(dppf)Cl2 (5.1 g, 7.0 mmol) and MeOH (10 mL), followed by TEA (14.3g, 140.1 mmol). The mixture was heated at 90 C overnight under carbon monoxide (5 MPa). The mixture was cooled to RT and the mixture was diluted with water, extracted with EA. The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 5% to 10% to give methyl 4-cyano-5-fluoro-2-methylbenzoate (7.33 g, 81%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 916792-13-7, its application will become more common.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); 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 17354-04-0 as follows. Formula: C10H10N2O4

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

According to the analysis of related databases, 17354-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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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. 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromo-2-methoxybenzonitrile

Compound 64 (E)-Methyl 3-(3-(N-((3′-cyano-4′-methoxy-[l,l’-biphenyl]-4- yl)methyl)cyclohexanecarboxamido)phenyl)acrylate [00430] A mixture of Intermediate 16 (500 mg, 0.99 mmol), 5-bromo-2-methoxy-benzonitrile (316 mg, 1.49 mmol), Cs2C03 (647 mg, 1.99 mmol), Pd(PPh3)4 (230 mg, 199 mmol) in DMF (6 mL) was degassed with vacuum/nitrogen cycles (3 chi), stirred at 90 C for 12 h, and then filtered. Saturated EDTA-2Na (20 mL) was added, and the reaction mixture was stirred for 1 h and then extracted with ethyl acetate (3 x20 mL). The combined organic layers were washed with water (3 x 15 mL) and brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by reverse-phase HPLC to give (E)-m ethyl 3-(3-(N-((3′-cyano-4′-methoxy- [l, l’-biphenyl]-4-yl)methyl)cyclohexanecarboxamido)phenyl)acrylate (110 mg, 22%) as a white solid. 1H MR (DMSO-i): delta 8.01 (d, IH), 7.96 (dd, IH), 7.58-7.70 (m, 5H), 7.42 (t, IH), 7.31 (d, IH), 7.24 (d, 2H), 7.17 (d, IH), 6.64 (d, IH), 4.89 (s., 2H), 3.95 (s, 3H), 3.71 (s, 3H), 2.19 (m, IH), 1.58-1.72 (m, 4H), 1.36-1.54 (m, 3H), 1.05-1.18 (m, IH), 0.89 (d, 2H); MS: 509.3 [M+H]+.

The synthetic route of 144649-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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