Category: ethers-buliding-blocks

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 14869-41-1 as follows. 14869-41-1

2-Chlorethoxyacetic acid (1.11 g, 8 mmol) is dissolved in dichloromethane (22 mL), and thereto are added thionyl chloride (1.17 mL, 16 mmol) and dimethylformamide (30 muL, 0.4 mmol) successively at room temperature. After stirring at room temperature for 2.5 hours, the mixture is concentrated, and the residue is dissolved in dichloromethane (22 mL). To the mixture are added methyl 4-aminobenzoate (661 mg, 4 mmol) and pyridine (674 muL, 8 mmol) under ice-cooling, followed by stirring overnight. The reaction solution is washed with dilute hydrochloric acid, dried, and concentrated. The residue is subjected to silica gel column chromatography to give ethyl 4-(2-chloroethoxyacetylamino)benzoate (540 mg, 23.6percent).

According to the analysis of related databases, 14869-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1640373; (2006); A1;,
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1579-40-4, Name is Di-p-tolyl Ether, 1579-40-4, 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.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

Statistics shows that Di-p-tolyl Ether is playing an increasingly important role. we look forward to future research findings about 1579-40-4.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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768-70-7, 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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 ¡Á 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3.

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; Dhara, Kalyan; Kapat, Ajoy; Ghosh, Tridev; Dash, Jyotirmayee; Synthesis; vol. 48; 23; (2016); p. 4226 – 4268;,
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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 2930-05-4 as follows. 2930-05-4

To a solution of LiAlH4 (7.56 g, 199 mmol) in anhydrous tetrahydrofuran (100 mL) was added a solution of 2-(benzyloxymethyl)oxirane (21.8 g, 132 mmol, 20.1 mL) in anhydrous tetrahydrofuran (300 mL) dropwise at 0 C. under nitrogen atmosphere. The mixture was then stirred for 1 hour. On completion, the reaction mixture was quenched with water (15 mL), then 15% sodium hydroxide solution (15 mL) was added, and the mixture was stirred for a further 15 minutes until no precipitate formed. Next, the inorganic salt precipitate was filtered off and the filter cake was washed with ethyl acetate (2¡Á100 mL). The combine organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a residue. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=2:1) to give the title compound (21.3 g, 96% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.40-7.29 (m, 5H), 4.57 (s, 2H), 4.08-3.94 (m, 1H), 3.49 (dd, J=3.2, 9.2 Hz, 1H), 3.30 (dd, J=8.4, 9.2 Hz, 1H), 2.40 (d, J=2.4 Hz, 1H), 1.16 (d, J=6.4 Hz, 3H).

According to the analysis of related databases, 2930-05-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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658-89-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 658-89-9 name is 4-(Trifluoromethoxy)benzene-1,2-diamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 3-isothiocyanato-N-methyl-3-[3-(trifluoromethyl)phenyl]propanamide (0.3 g, 1 mmol) (from step 3) and 4-(trifluoromethoxy)benzene-l,2-diamine (0.2 g, 1 mmol) in dichloromethane (100 mL) was stirred at ambient temperature. After 4 h, the reaction mixture was concentrated to afford the crude product (0.50 g) as yellow gum. It was purified by flash column using 230-400 silica gel, the product fraction was eluted using 40 % ethyl acetate in hexane to afford 3-({[2-amino-5- (trifluoromethoxy)phenyl]carbamothioyl} amino)-N-methyl-3 – [3 – (trifluoromethyl)phenyl]propanamide (0.4 g) as an off-white solid. MS: m/z 481 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethoxy)benzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; ACESION PHARMA APS; S?RENSEN, Ulrik Svane; METE, Anthonio; (90 pag.)WO2019/34603; (2019); A1;,
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5397-31-9, 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. 5397-31-9, name is 3-((2-Ethylhexyl)oxy)propan-1-amine, This compound has unique chemical properties. The synthetic route is as follows.

52 grams of 3 amino BENZOTRIFLUORIDE is mixed with 50 grams of 2 methyl 2 butanol and 200 mis of water are added, followed by 38 grams of sulfuric acid 96%. The mixture is iced to 5C and diazotized by the addition of 55 grams of a 40% solution of sodium nitrite. When the solution has become clear excess nitrous acid is reduced with SULFAMIC acid. This diazo is then added to a solution of 38 grams of 2 amino para cresol which has been dissolved in a mixture of 100 grams of 2 methyl 2 butanol and 100 grams of an aqueous solution containing 0.3 equivalents of naphthalene SULFONIC acids to which 1 gram each of acrylic acid and butyl methacrylate have been added as free radical suppressors. Coupling proceeds quickly at 5-10C and is brought to completion by the addition of sufficient sodium acetate solution to raise the pH to 2.5. When the azo coupling is complete 150 grams of toluene and 55 grams of hydrochloric acid 32% is added to the reaction. 60 grams of a 40% solution of sodium nitrite is now added to diazotize the amino azo compound. When this reaction is complete 0.3 molar equivalents of a composition made by condensing 0.3 equivalents of 3 amino phenol and 0.6 equivalents of 2 ethyl hexyl glycidyl ether dissolved as an 80% solution in toluene is added to the system. Coupling proceeds readily with the formation of a magenta red bisazo dye. The coupling is now adjusted to pH 9 by the addition of aqueous ammonia and heated to 60C. 0.3 molar equivalents of nickel chloride are now added to the system together with sufficient ammonia to stop the pH falling below 8.0. Formation of the metal complex is essentially instant as determined by TLC. 60 grams of 2 ethyl hexoxy propylamine is now added to the system and after a few minutes stirring agitation is stopped and the dye layer allowed to separate as an upper phase. The dye is then dried under vacuum to 110C and brought to a total weight of 700 grams with n-propanol. The product is a violet black with very good light fastness and solvent compatibility.

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; UNITED COLOR MANUFACTURING, INC.; WO2005/30875; (2005); A2;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 450-88-4 name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 450-88-4

Intermediate Example Int20.014-(4-bromo-3-methoxyphenoxy)-1 -methylpiperidine To a stirred suspension of sodium hydride (1.76 g; 60% w/w sodium hydride in oil) in DMF (55 mL) was added 1 -methylpiperidin-4-ol (3.37 g) at 0 C. The mixture was stirred at room temperature for 30 minutes. 1 -bromo-4-fluoro-2- methoxybenzene (3.0 g) was added and the mixture was stirred at 100 C for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica- gel chromatography gave 3.65 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje Margret; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; KOPPITZ, Marcus; STOeCKIGT, Detlef; PRIEN, Olaf; WO2011/157688; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4179-19-5, name is 3,5-Dimethoxytoluene, 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 4179-19-5, 4179-19-5

1,3-Dimethoxy-5-methylbenzene (30 g, 0.20 mol)And dichloromethane (900 mL) was added to a dry round bottom flask (1 L).Cooling to the above solution in an ice bath sulfuryl chloride (52.5 g, 0.40 mol) was added dropwise.After the dropwise addition was completed, the mixture was stirred at room temperature overnight. After the reaction,Add sodium bicarbonate aqueous sodium hydrogencarbonate solution to adjust pH=8, extract with dichloromethane,Washed with dilute hydrochloric acid, distilled water, and dried,Concentration under reduced pressure gave the compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene (31 g, white solid).

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, 3,5-Dimethoxytoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wang Hui; (76 pag.)CN109721600; (2019); A;,
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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. 41406-00-2, name is 3-Isopropoxyaniline, A new synthetic method of this compound is introduced below., 41406-00-2

General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol.

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; Gonec, Tomas; Zadrazilova, Iveta; Nevin, Eoghan; Kauerova, Tereza; Pesko, Matus; Kos, Jiri; Oravec, Michal; Kollar, Peter; Coffey, Aidan; O’Mahony, Jim; Cizek, Alois; Kralova, Katarina; Jampilek, Josef; Molecules; vol. 20; 6; (2015); p. 9767 – 9787;,
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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. 583-19-7, name is 1-Bromo-2-ethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., 583-19-7

3-(2-bromoacetyl)-8-chloro-2H-chromen-2-one (150 mg, 0.54 mmol) and l-bromo-2-ethoxybenzene (108 mg, 0.54 mmol) were reacted in a microwave in the presence of CS2CO3 (528 mg, 1.62 mmol), Pd2(dba)3 (40mg, 0.054mmol.), xantphose (60mg, 0.108mmol), and dioxane (2 mL) at 160C for 15 minutes. The resulting product was then purified by pre-HPLC to yield 8-chloro-3-(2-(2-ethoxyphenylamino)thiazol-4-yl)-2H-chromen-2-one (20 mg, 10%) as a yellow solid. ESI-MS (EI+, m/z): 399.1 [M+l]+; 1HNMR (500 MHz, DMSO-<): delta 1.40 (t, J = 7 Hz, 3H), 4.14 (q, J= 7 Hz, 2H), 6.99-7.05 (m, 3H), 7.39 (t, J = 8 Hz, 1H), 7.76-7.79 (m, 2H), 7.93 (t, J= 7 Hz, 1H), 8.48-8.49 (m, 1H), 8.65 (s, 1H), 9.54 (s, 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; DISCOVERYBIOMED, INC.; SCHWIEBERT, Erik; STREIFF, John; DIXON, John; GAO, Hongwu; WO2014/152213; (2014); A2;,
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