Month: November 2020

929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

A 1 moles of a double-terminal amine polyether (structure of formula (2), R 2 = R 3 = H, n = 3), 18 moles of dichloroethane and 1 mole of sodium hydroxide (an aqueous solution having a concentration of 20% by weight) were charged into a reaction flask equipped with a cooling apparatus, 4 C, then slowly add 1 mole of acryloyl chloride, the temperature of the addition process does not exceed 15 C, after the addition of acryloyl chloride, the reaction is carried out at 15 C for 3 hours; the resulting reaction is allowed to stand and the organic phase is separated, Washed with saturated aqueous NaCl solution 3 times, dried with anhydrous sodium sulfate, the organic solvent was distilled off to obtain a crude product of orange-red viscous liquid, and the crude product was washed with acetone to obtain the product of polymerization grade. The product of the polymerization stage was confirmed to be a monomer represented by the formula (1) (wherein Ri = R2 = R3 = H, n= 3) using an infrared spectrum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; CHINA PETROLEUM & CHEMICAL CORPORATION;.; DRILLINGRESEARCH INSTITUTE OF SINOPEC ZHONGYUAN PETROLEUM ENGINEERING CO., LTD; WANG, ZHONGHUA; (12 pag.)CN104926678; (2017); B;,
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2674-34-2, These common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, 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.

To a solution of A (146 g, 50 mmol) in 250 ml of THF was slowly added n-butyllithium (50 mL, 2.5 M/L in hexane) at -78 C under argon. The mixture was kept at -78 for 1 hour. Then, pinacol borate (25.3 g, 100 mmol) was added, followed by slowly warming to room temperature, and the mixture was stirred overnight. The mixture was extracted twice with diethyl ether and washed with distilled water and brine. Further purification by silica gel column chromatography using hexane as eluent.A white solid (15 g, yield 80%), i.e., 2,5-dimethoxy-1,4-diborate benzene (B), was obtained.

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 2674-34-2.

Reference:
Patent; Chinese Academy Of Sciences Chemical Institute; Li Xiaojun; Li Yongfang; Pan Fei; Zhang Zhiguo; (21 pag.)CN109748925; (2019); A;,
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321-28-8, A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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 a solution of the selected anisole or biphenyl (13.0mmol) in 30mL of dry CH2Cl2 at 0 C, p-toluoylchloride (2g, 13.0mmol), and AlCl3 (3g, 22.05mmol) were added and the mixture was stirred at rt overnight. After addition of ice, the mixture was diluted with CH2Cl2, washed with NaHCO3 saturated solution, dried and evaporated to dryness.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gobbi, Silvia; Hu, Qingzhong; Foschi, Giacomo; Catanzaro, Elena; Belluti, Federica; Rampa, Angela; Fimognari, Carmela; Hartmann, Rolf W.; Bisi, Alessandra; Bioorganic Chemistry; vol. 86; (2019); p. 401 – 409;,
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929-75-9, 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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 3-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-4-methyl-2H-chromen-2-one (19, 200 mg, 0.268 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 52 mg, 0.27 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (119 mg, 0.268 mmol), and the mixture was stirred at the same temperature for 2 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (20:1) to give the desired product 21c (84 mg, 34%). Mp 307.4+/-0.2 C; 1H NMR (500 MHz, DMF-d7): delta=8.93 (s, 1H), 8.06 (br t, J=5.8 Hz, 1H), 7.97 (s, 2H), 7.87 (s, 1H), 4.75 (t, J=7.0 Hz, 2H), 3.80 (t, J=5.8 Hz, 2H), 3.69 (s, 2H), 3.65-3.70 (m, 2H), 3.62-3.65 (m, 4H), 3.57-3.60 (m, 4H), 3.36 (q, J=5.8 Hz, 2H), 3.31 (t, J=5.8 Hz, 2H), 2.51 (s, 3H), 2.44-2.57 (m, 2H), 2.32-2.39 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=169.3, 161.2, 152.9, 149.2, 145.7, 134.2, 126.3, 122.9, 121.3, 120.8, 120.0, 112.4, 70.24, 70.16, 70.09, 70.07, 69.5, 67.1, 49.0, 39.9, 39.3, 27.7, 21.4, 14.9 ppm; IR (ATR, neat): nu=2927, 1703 (CO), 1654 (CO), 1614, 1561, 1200, 1146, 1113, 835 cm-1; MS (ESI): m/z: 920 [M+H+]; HRMS (EI): m/z calcd for C33H34F17N5O6: 919.2238 [M+]; [M+] not found.

The synthetic route of 1,11-Diamino-3,6,9-trioxaundecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
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Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. 2674-34-2

K2CO3 (1.13g, 8.19mmol), boronate ester 17 (800mg, 1.78mmol), and dibromoarene 11 (176mg, 0.593mmol) in toluene (20mL), EtOH (4mL) and H2O (2mL) was sparged with Ar for 1h. Pd(PPh3)4 (73mg, 0.063mmol) was added, the mixture was sparged with Ar for an additional 20min, and then heated 90C for 16h. The reaction mixture was cooled to rt and diluted with 50mL of H2O. The reaction mixture was extracted with Et2O (3¡Á50mL). The combined organics were washed with 150mL of brine, dried with Na2SO4, and the solvents were removed under vacuum. The product was isolated via column chromatography as a white solid (433mg, 99%), mp 248-250C. 1H NMR (CDCl3): delta 8.09 (d, J=1.8Hz, 2H), 7.80 (dd, J=8.0, 1.8Hz, 2H), 7.53 (d, J=8.0Hz, 2H), 7.49 (s, 6H), 6.91 (s, 2H), 3.76 (s, 12H), 1.41 (s, 36H). 13C NMR (CDCl3): delta 169.0, 151.3, 150.3, 141.6, 136.8, 132.2, 131.6, 130.3, 129.9, 128.4, 121.8, 121.7, 112.8, 56.0, 51.8, 35.0, 31.5. FTIR (cm-1): 1720.79. UV-vis (CH2Cl2) lowest E abs lambdamax [nm] ( [M-1cm-1]): 337 (22,801). Em. (CH2Cl2) lambdamax [nm]: 424. Anal. Calcd for C52H62O6: C, 79.76; H, 7.98. Found: C, 77.41; H, 8.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2674-34-2, its application will become more common.

Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
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Adding a certain compound to certain chemical reactions, such as: 437-83-2, name is 3-Fluoro-2-methoxyaniline, belongs to ethers-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 437-83-2, 437-83-2

NaNO2 (12.0 g, 1?73 mmol, in 40 m of water) solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 m of hydrobromic acid (4?7 %) and 100 m of water at -5 o Oc and stirred for 1 hour.This solution was then added slowly to the suspension of cuBr (45.2 g, 315 mmol) in 50 m of hydrobromic acid (4?7 %) at O Oc. The resulting mixture was stirred at o Oc for 1 hour then warmed to so Oc and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organie layer was washed with brine, dried oyer anhydrous Na2504 and concentrated to giye 1-bromo-3-fluoro-2-methoxybenzene.

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, 3-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
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461-82-5, The chemical industry reduces the impact on the environment during synthesis 461-82-5, name is 4-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

N-Bromosuccinamide (3.62 g, 20.34 mmol) was added to a solution of commercially available 4-(trifluoromethoxy)aniline (3.00 g, 1 6.95 mmol) in acetonitrile (30 mL) at 0C. The resulting mixture was allowed to warm to roomtemperature and stirred for 4 hours. The solvent was removed under reduced pressure to give the crude product which was purified by column chromatography eluting in 10% ethyl acetat/hexane to afford the title compound as brown oil (3.6 gm, 83%): 1 H NMR (400 MHz, CDCI3) oe: 4.11 (bs, 2 H), 6.73 (d, 1 H), 6.99 (dd, 1 H), 7.31 (d, 1 H). LC-Ms (m/z): [M-H] = 253.1.

The chemical industry reduces the impact on the environment during synthesis 461-82-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
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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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., 589-10-6

To a stirred solution of methyl isonipecotate (4. 00G, 28.00 mmol) and phenoxyethyl bromide (4. 00g, 20.00 mmol) in acetonitrile (30 ml) was added sodium hydrogen carbonate (7. 00G, 84.00 mmol) and the reaction stirred at 80C for 20 hours. The reaction was cooled, filtered and concentrated under reduced pressure to give a crude brown oil. Purification by column chromatography (7% methanol: dichloromethane) gave the required compound as a light brown oil (4.8g, 65%). oH (270 MHz; CDCL3 ; ME4SI), 1.71-2. 37 (7H, m), 2.79 (2H, t, J 6. 0), 2.93-3. 0 (2H, m) 3.68 (3H, s), 4.10 (2H, t, J 6.0), 6.89-6. 97 (3H, m), 7.24-7. 32 (2H, m). HPLC 99%, m/z (APCI), 264.20 (100% [M+H] +), 232 (40, C14HL802N), 170 (47, C9H1602N).

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; BIOFOCUS PLC; WO2004/58259; (2004); 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., 20469-65-2

2.171 g of 1-bromo-3,5-dimethoxybenzene and 3.810 g of boronic acid pinacol ester were dissolved in 85 ml of dioxane,2.945 g of potassium acetate and 0.732 g of [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride were added, and the temperature was raised under argonTo 85 C, stirring for 12 hours after the stop heating, the reaction solution, a small amount of ethyl acetate washing cake, the filtrate concentrated evaporated, residualThe residue was chromatographed (petroleum ether: ethyl acetate = 99: 1-98: 2, V / V) to give 2.462 g of a white solid in 93.2% yield.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Duan Wenhu; Geng Meiyu; Zhao Bin; Ding Jian; Ai Jing; Fan Jun; Peng Xia; Yan Wei; Chen Yi; (77 pag.)CN106146493; (2016); A;,
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19056-40-7, 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 19056-40-7 as follows.

To a solution of ethyl (2Z)-3-(methylamino)-3-phenylacrylate (4.47 g, 21.77 mmol) in DCM (100 mL) was added 4-bromo-3-methoxyaniline (4 g, 19.80 mmol) and PPTS (5.47 g, 21.77 mmol). The mixture was then heated to reflux for 24h. At this time crude IH NMR revealed nearly complete consumption of the aniline. The reaction was then cooled to r.t.,fltered, and the solvent was removed in vacuo. The crude product was purified on silica (75percent DCM/hexanes) to yield ethyl (2Z)-3- [(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate (6.5 g, 87percent) which was used as is in subsequent reactions. 1H NMR (500 MHz, CDCl3) ppm: 10.32 (br s, IH), 7.32 (m, 5H), 7.20 (d, J = 8.5 Hz, IH), 6.19 (dd, J = 8.5 Hz, 2.5 Hz, IH), 6.11 (d, J = 2.5 z, IH), 5.03 (s, IH), 4.21 (q, J = 7.0 Hz, 2H), 3.50 (s, 3H), 1.32 (t, J = 7.0 Hz, 3H).

According to the analysis of related databases, 4-Bromo-3-methoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/119061; (2006); A2;,
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