Ethers-buliding-blocks

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. 111-95-5, name is Bis(2-methoxyethyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 111-95-5

In a 100 ml eggplant type flask, 3.6 ml (25 mmol) of bis (2-methoxyethyl) amine,3.2 g (25 mmol) of phloroglucinol and 30 ml of THF were added and stirred. After 48 hours,The reaction was confirmed by TLC (SiO 2, developing solvent hexane: acetone = 1: 1), followed by extraction with chloroform, and the solvent was distilled off under reduced pressure to obtain a black viscous substance (yield 5.1 g, yield 86 %).

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Satoru: Yamagata University; Kido Junji; Sasabe Hisa Hiroshi; Sasaki Isamu; (15 pag.)JP6281975; (2018); B2;,
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1515-81-7, 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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), thiol (1.0 mmol), p-methoxybenzylmethyl ether (167 mL,167 mg, 1.10 mmol), TMSOTf (271 muL, 333 mg, 1.50 mmol), anddiisopropylethylamine (244 muL, 181 mg, 1.40 mmol). The homogenous mixture was stirredovernight and then passed through a column of silica (2 cm x 1 cm) with Et2O.The solvent was removed in vacuo and the residue was purified by columnchromatography (0-2% EtOAc/hexanes).

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Reference:
Article; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, 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. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, s).

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, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); 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

Into a 500-mL 3-necked round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 1,3-dimethoxy-5-methylbenzene (5 g, 32.85 mmol, 1.00 equiv) in dichloromethane (150 mL). This was followed by the addition of sulfuroyl dichloride (8.869 g, 65.71 mmol, 2.00 equiv) dropwise with stirring at 00 C. Theresulting solution was stirred overnight at room temperature. The pH value of the solution was adjusted to 8 with sodium carbonate (sat. aq.). The resulting solution was extracted with dichloromethane, and the combined organic layers were concentrated under vacuum. The resulting mixture was washed with hexane to give 5.36 g (74%) of 2,4-dichloro-1,5-dimethoxy- 3-methylbenzene as a 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; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth A.; VERNER, Erik; WO2014/182829; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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 321-28-8, 321-28-8

General procedure: To a 5 mL screw-capped vial equipped with a 15¡Á10 mm spinvane triangular-shaped Teflon stirbar, simple arene 1(0.5 mmol), saccharin (1.0 mmol), Selectfluor (1.0 mmol), K2CO3 (1.0 mmol) and CuCl (0.1 mmol) were added in nitromethane (3.0 mL). The mixture was sealed with aTeflon-lined cap and stirred at 90 C for 6.0 h (monitoredby TLC), extracted with dichloromethane (5¡Á3 mL), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel column chromatography to give aromatic amine 2. The characterizations of aromatic amines 2 and 4 were listed in the Supporting Information online.

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, 1-Fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sun, Kai; Li, Yan; Zhang, Qian; Science China Chemistry; vol. 58; 8; (2015); p. 1354 – 1358;,
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3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below.

5.0 g (20.0 mmol) of the intermediate (A-11), 4.8 g (30.0 mmol) of (dimethylamino)acetaldehyde diethylacetal, and 78 ml of acetic acid were loaded and the mixture was stirred for 96 hr while being heated at 140¡ãC. The reaction solution was cooled to room temperature and then the solvent was removed by evaporation under reduced pressure. The resultant residue was purified by silica gel column chromatography to give 2.3 g (8.4 mmol, yield: 42 molpercent) of an intermediate (A-12). FD-MS, m/z 274 [M]

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; Nippon Steel & Sumikin Chemical Co., Ltd.; ISHIYAMA, Takaya; HAYASHIDA, Hiroyuki; SAKAI, Mitsuru; NIINA, Masashi; SHIRAISHI, Kazuto; YOSHIMURA, Kazuaki; EP2687530; (2014); A1;,
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20469-65-2, 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 20469-65-2 as follows.

1-iodo-3,5-dimethoxybenzene:A dried round bottom flaks was charged with 1-bromo-3,5-dimethoxy- benzene (15.0 g, 69.1 mmol) and dry tetrahydrofuran (275 cm3). The resulting solution was cooled down to -78 0C, then n-butyllithium (2.5 M in hexanes, 29.0 cm3, 72.6 mmol) was added dropwise over 10 minutes. The mixture was stirred at -78 0C for 1 hour, then 1,2-iodoethane (20.5 g, 72.6 mmol) in dry tetrahydrofuran (75 cm3) was added rapidly to the solution. After an additional 1 hour at -78 0C, the resulting mixture was warmed to room temperature and stirred overnight. The mixture was poured into saturated sodium thiosulfate solution (200 cm3), extracted with diethyl ether four times and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from methanol to obtain the title product as a white crystalline solid(13.0 g, yield 71 %). NMR (1H, 300 MHz1 CDCI3) : delta 6.85 (d, J = 2.3 Hz, 2H); 6.40 (t, J = 2.3 Hz, 1 H); 3.76 (s, 6H).

According to the analysis of related databases, 1-Bromo-3,5-dimethoxybenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; BLOUIN, Nicolas; MITCHELL, William; WANG, Changsheng; TIERNEY, Steven; WO2011/18144; (2011); A2;,
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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. 2752-17-2, name is 2,2′-Oxydiethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2752-17-2

General procedure: The parent compound 9 (0.36g, 1mmol) was dissolved in CH2Cl2 (6mL), then oxalyl chloride (4mmol) was added dropwise. The mixture was stirred for 4h at the room temperature. The solvent and excess oxalyl chloride was evaporated to obtain the crude farnesylthiosalicyl chloride. Then to a mixture of different diamines (1.5mmol) and TEA (0.45mmol) in 10mL CH2Cl2 was added dropwise the CH2Cl2 solution (5mL) of farnesylthiosalicyl chloride (1.12g, 0.3mmol) at 0C over 1h. After stirring for another 0.5h the reaction was quenched by adding 20mL water. The mixture was extracted with CH2Cl2 (20mL¡Á3) and the organic layer was combined, washed with brine, dried with anhydrous Na2SO4 and concentrated in vacuo. The crude product was separated by silica gel chromatography (petroleum ether/ethyl acetate=1:1 v/v; then CH2Cl2-MeOH=4:1 as the eluent) to afford compound 10a-g and 11a-g as yellowish oil.

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ling, Yong; Wang, Zhiqiang; Zhu, Hongyan; Wang, Xuemin; Zhang, Wei; Wang, Xinyang; Chen, Li; Huang, Zhangjian; Zhang, Yihua; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 374 – 380;,
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Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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. 54149-17-6

Example 20 Synthesis and Utility of 2,7-dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene Benzyltriethylammonium chloride (3.19 g, 14 mmole, 0.077 eq) and 2,7-dibromofluorene (59 g, 182 mmole, 1 equiv.) were suspended in 178 mL DMSO. 50% aqeous NaOH 80 mL was added. 1-Bromo-2-(2-methoxyethoxy)ethane (80 g, 437 mmole, 2.4 equiv.) was then added in small portions. The reaction was stirred at room temperature for 2 hours before it was stopped and the aqueous layer was extracted with ether. The combined ether layers were washed with water five times and dried over Na2SO4. The organic layer was filtered, evaporated to dryness and the residual was flash chromatographed on a silica-gel column to give the pure compound (73 g), in a yield of 86%. This compound can be used for example to modify the solubility parameter of the compound of Example 16. To do this 2,7-dibromo-9,9-bis(3,6-dioxaheptyl)-fluorene is used in place of 2,7-dibromo-9,9-dioctyl fluorene in Example 16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54149-17-6, its application will become more common.

Reference:
Patent; 3M Innovative Properties Company; US7271406; (2007); B2;,
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A common compound: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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. 702-24-9

A mixture of ethyl 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate (1.5 g, 5.55 mmol), N-(4- methoxybenzyl)-N-methylamine (1.67 g, 11.04 mmol) and N,N-diisopropylethylamine (2.75 ml, 16.63 mmol) in ethanol (25ml) was stirred at 85 ¡ãC for 96h. The mixture was concentracted to dryness and the residue was purified by column chromatography (eluent 50percent ethyl acetate: petroleum ether) to afford ethyl 6-[(4-methoxyphenyl)methyl-methyl-amino]pyrazolo[1,5- a]pyrimidine-3-carboxylate (1120 mg, 57.5percent yield) as a yellow solid. (ESI): m/z = 341.2 [M+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, 702-24-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian, C.; GOBBI, Alberto; KIEFER, James, Richard, Jr.; KOLESNIKOV, Aleksandr; OLIVERO, Alan, G.; DROBNICK, Joy; LIANG, Jun; RAJAPAKSA, Naomi; (846 pag.)WO2017/108723; (2017); A2;,
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