Category: ethers-buliding-blocks

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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., 1535-75-7

General procedure: The benzoic acid 1 (1.50 g, 7.46 mmol) was refluxed in neat thionyl chloride (2 mL) for 2 h then allowed to cool to rt. The excess thionyl chloride was removed under reduced pressure to yield the crude acid chloride. A solution of anilines in DCM (10 mL) was added to a solution of the crude acid chloride in DCM (10 mL), followed by triethylamine (2.25 mL). The mixture was stirred at room temperature under argon for 3 h, after which the solvent was removed. The residue was purified by recrystallization (petroleum ether- ethyl acetate) to afford the product.

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; Liu, Fang; Venter, Henrietta; Bi, Fangchao; Semple, Susan J.; Liu, Jingru; Jin, Chaobin; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3399 – 3402;,
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A common compound: 2752-17-2, name is 2,2′-Oxydiethanamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2752-17-2

For the synthesis of H2L, salicylic aldehyde (10 mM, 1.22 g) in EtOH (5 mL) was added dropwise to 5mL of an EtOH solution of 3-oxapentane-1,5-diamine (5 mM, 0.52 g). After completion of addition, the solution was stirred for an additional 4 h at 78 C. After cooling to room temperature, the precipitate was filtered. The product was dried in vacuo, giving a yellow crystalline solid. Yield: 1.19 g (68.5%).

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, 2752-17-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Huilu; Pan, Guolong; Bai, Yuchen; Wang, Hua; Kong, Jin; Shi, Furong; Zhang, Yanhui; Wang, Xiaoli; Journal of Coordination Chemistry; vol. 66; 15; (2013); p. 2634 – 2646;,
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1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-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. 1462-37-9

To a stirred solution of 3,5-dimethyl lH-pyrazole-3,5-dicarboxylate (10 g, 54.30 mmol, 1 equiv.) and [(2-bromoethoxy)methyl] benzene (12.8 g, 59.51 mmol, 1.096 equiv.) in MeCN (200 mL) was added K2CO3 (11.3 g, 81.46 mmol, 1.5 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 90 ¡ãC. The mixture was allowed to cool down to room temperature and then quenched with water. The resulting mixture was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with PE/EtOAc (10: 1) to afford the title compound as a yellow oil in 96.22percent yield.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
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20781-20-8, 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 20781-20-8 as follows.

To a solution of(2R,6R,I 1R)-tert-butyl 6,1 i-dimethyh8(trifiuoromethyl)sulfonyl)oxy)-i ,2,5,6-tetrahydro-2,6-methanobenzo[diazocine3(4H)carboxyiate (5.32 g, 11.8 mmoi) in degassed dimethyl sulfone (50 mL), wasadded Nhydroxysuccinimide (233 g, 23.7 rnmoi), palladium acetate (265 nig, 118 mmol), triethylamine (3.3 mL, 23,7 mmoi) and 4,5-bis(diphenylphosphino)95- dimethyixanthene (683 mg, 1.1 8 mrnoi). The reaction mixture was heated with carbon monoxide (latm) at 70C overnight. The reaction mixture was cooled toambient temperature and 2,4-dimethoxybenzylamine (2.17 mg. 13.0 rnmol) added. The mixture was stirred for 2 hours diluted with ethyl acetate (800 rnL), and filtered tiu?ough cehte. The organic solution was washed twice with water (800 inL), hrine (300 mL), and dried (MgSO4). Filtration and removal of the solvent under reduced pressure gave crude material that was purified by silica chromatography(EtOAc(i):heptanes(l)) to give (2R,6R.l 1R)-tert-butyi 8-((2,4- dimethoxyhenzyl)carhamoyi)6, Ii dimethyl- I ,2,5,6..tetrahydro-2,6- methanohenzo[dazocine-3(4i-I)-carhoxyla1e (4.0 g, 68% yield); L.C/MS(M+H) = 495,3,

According to the analysis of related databases, (2,4-Dimethoxyphenyl)methanamine, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALKERMES PHARMA IRELAND LIMTED; DEAVER, Dan; BLUMBERG, Laura, Cook; EYERMAN, David; WYNN, Thomas; WO2014/190271; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 20059-73-8, name is 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, 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 20059-73-8, 20059-73-8

EXAMPLE 6 N-[4-[2-(Dimethylamino)ethoxy]benzyl]-2-methoxy-5-sulfamoylbenzamide To a cooled suspension of 14.3 g of 2-methoxy-5-sulfamoylbenzoic acid in 60 ml of tetrahydrofuran were successively added dropwise 6.25 g of triethylamine and 7.45 g of pivaloyl chloride with stirring. The mixture was stirred at the same temperature for 1 hour and then a solution of 10.0 g of 4-[2-(dimethylamino)ethoxy]-benzylamine in 40 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 14 hours and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate to give a precipitate, which was washed with water and ethyl acetate, of 16.6 g of colorless crystals. Recrystallization of the crystals from ethanol gave the title compound as colorless needles, m.p. 154-155 C. Analysis for C19 H25 N3 O5 S: Calculated %: C, 56.00; H, 6.18; N, 10.31. Found %: C, 55.71; H, 6.21; N, 10.02.

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-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hokuriku Pharmaceutical Co., Ltd.; US4983633; (1991); A;,
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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 767-91-9 as follows. 767-91-9

General procedure: CuSO4¡¤5H2O (5 x 10-3 mmol), L4 (5 x 10-3 mmol), azide (0.5 mmol) and terminal alkyne (0.6 mmol) were placed in the reaction vial where 1 mL of water was added. The reaction mixture was stirred in air at room temperature, and the progress of the reaction was monitored by TLC. After completion of the reaction, the reaction solution was extracted with DCM and the collected organic phase was dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure and the crude products were purified by column chromatography (eluted with petroleum ether/EtOAc = 10:1) to yield pure 1,4-disubstituted 1,2,3-triazole.

According to the analysis of related databases, 767-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Siyu; Jia, Kai; Cheng, Jiajia; Chen, Yu; Yuan, Yaofeng; Tetrahedron Letters; vol. 58; 38; (2017); p. 3717 – 3721;,
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41406-00-2, A common compound: 41406-00-2, name is 3-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: 2-Hydroxynaphthalene-1-carboxylic acid or 1-hydroxynaphthalene-2-carboxylic acid (5.30 mmol) and appropriate alkoxyaniline (5.30 mmol) were suspended in 30 mL of dry chlorobenzene. Phosphorous trichloride (2.65 mmol) was added dropwise, and reacting mixture was heated in the microwave reactor for 15 min at 130 C using infrared flask-surface control of temperature. Solvent was evaporated in vacuum; residue solid was washed with 2M HCl and crystallized from aqueous ethanol. If necessary, column chromatography was used for further purification (mobile phase DCM:MeOH 19:1).

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

Reference:
Article; Gonec, Tomas; Pospisilova, Sarka; Kauerova, Tereza; Kos, Jiri; Dohanosova, Jana; Oravec, Michal; Kollar, Peter; Coffey, Aidan; Liptaj, Tibor; Cizek, Alois; Jampilek, Josef; Molecules; vol. 21; 8; (2016);,
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24332-20-5, The chemical industry reduces the impact on the environment during synthesis 24332-20-5, name is 1,1,2-Trimethoxyethane, I believe this compound will play a more active role in future production and life.

a) 5-Methoxypyrimidin-2-amine (1-22). NaOH, MeOH Phosphorus pentachloride (8.07 g; 38.78 mmol; 1 eq) was added portion-wise to methoxyacetaldehyde dimethyl acetal (5 mL; 38.78 mmol; 1 eq) kept at 20C. The reaction mixture was heated at 60C for 1 hour and 15 minutes, then cooled down to 0C, before adding anhydrous dimethylformamide (9 mL; 116.3 mmol; 3 eq) dropwise. The reaction mixture was heated at 70C for 45 minutes, then cooled at 0C before adding methanol (40 mL) followed by sodium hydroxide (20.1 g; 504 mmol; 13 eq) and guanidine nitrate (9.46 g; 77.56 mmol; 2 eq). The reaction mixture was stirred at 0C for 15 minutes. The reaction mixture was allowed to reach at room temperature and methanol was evaporated. The resulting solution was heated at 100C for 1 hour and 30 minutes. Water (200 mL) and ice was added and the aqueous layer was extracted with dichloromethane (3 x 250 mL). The combined organic layers were washed with saturated sodium chloride (150 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title compound 5- methoxypyrimidin-2-amine was obtained in 53% yield (2.6 g) as a brown solid. 1H- NMR (DMSO-d6): delta (ppm) 3.73 (s, 3H), 6.16 (s, 2H) , 8.04 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 1,1,2-Trimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
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456-49-5,Some common heterocyclic compound, 456-49-5, name is 1-Fluoro-3-methoxybenzene, molecular formula is C7H7FO, 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 -butyllithium (5.0 mL, 7.93 mmol, 1.6 M in -hexane) in freshly distilled THF (20 mL) at -70 C were added a solution of compound 1-1 (1.0 g, 7.93 mmol) in THF (10 mL) and a solution of I2 (2.32 g, 9.12 mmol) in THF (15 mL) dropwise respectively. At the end of the addition, the mixture was stirred for 20 mins and allowed to warm up to -60 C and then an aqueous solution of sodium thiosulfate (3.0 mL, 10%) was added to the mixture. After the reaction was completed, the mixture was quenched by adding an aqueous ammonium chloride solution (10 mL) slowly. The THF was removed in vacuo and the aqueous phase was extracted with -hexane (50 mL x 3). The combined organic layers were washed with an aqueous sodium thiosulfate solution (10%) and water, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as oil (1.6 g, 80%). The compound was characterized by the following spectroscopic data: lli NMR (400 MHz, CDCI3): delta 6.79, 6.77, 6.75 (d, dd, d, 1H), 6.63, 6.62, 6.60, 6.58 (s, d, d, s, 1H), 6.53-6.52, 6.51-6.50 (m, m, 1H) ppm.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; HU, Bailin; LI, Shifeng; WU, Xiwei; TANG, Changhua; WANG, Chenglin; FANG, Qinghong; YU, Quanxing; ZHANG, Zhikeng; WO2014/131315; (2014); A1;,
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20469-65-2, Adding a certain compound to certain chemical reactions, such as: 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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 20469-65-2.

the mixture 1-bromo-3,5-dimethoxybenzene 1c (6.51g, 30mmol), trimethylsilylacetylene (8.8g, 90mmol), bis (triphenylphosphine) palladium chloride (1.05g, 1.5mmol), cuprous iodide (0.56g, 3.0mmol), triethylamine (80 mL) and N, N-dimethylformamide (150 mL) were heated to 80 C. and stirred under nitrogen protection for 12 hours.The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether) to obtain the target product ((3,5-dimethoxyphenyl) ethynyl) trimethylsilane 1d (6.2 g, brown solid), yield: 88%.

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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