Category: 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. 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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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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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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75148-49-1, These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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 mixture of 3-bromobenzaldehyde diethylacetal (1.495 g, 5.77 mmol) and bis(triphenylphoshine)palladium(II) dichloride (206 mg, 0.29 mmol) in dimethoxyethane (30 mL) at room temperature under nitrogen, 2-thiopheneboronic acid (1.189 g, 9.29 mmol) and aquesou sodium bicarbonate (1M, 29 mL) were added. The mixture was heated to reflux overnight, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give a mixture of 2-(3-(diethoxymethyl)phenyl)thiophene and 14-1. This material was taken up in 1:1 methanol:water (30 mL) and concentrated sulfuric acid (1 mL) was added. The mixture was heated to reflux for 2 hours, cooled to room temperature and concentrated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and concentrated.

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 75148-49-1.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. 54149-17-6

(2S,6R, I lR)-6,l l -dimethyl-l-oxo- l ,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-y trifluoromethanesulfonate hydrochloride (120 mg, 0.33 mmol), Cs2C03 (214.9 mg, 0.6494 mmol) and mPEG2-Br (78.45 mg, 0.4286 mmol) were dissolved in acetonitrile. The mixture was heated to 75 C for 16 h and cooled to room temperature. The mixture was concentrated under vacuum and purified by flash chromatography to yield (2S,6R,l lR)-8-hydroxy-3-(2- (2-methoxyethoxy) ethyl)-6,l l-dimethyl-3,4,5,6-tetrahydro-2,6-methanobenzo[d]azocin- l(2H)-one (14) (51.5 mg, 47% yield). NMR (500 MHz, CDC13): delta 8.02 (d, 1 H), 6.85 (m, 2H), 4.21-4.23 (m, 2H), 3.89 (t, 2H), 3.57-3.59 (m, 2H), 3.39 (s, 3H), 3.27 (d, 1H), 2.72-2.75 (m, 1 H), 2.55-2.61 (m, 1 H), 2.08-2.13 (m, 1H), 1.87-1.94 (m, 1H), 1.45-1.48 (m, 1H), 1.41 (s, 3H), 0.85 (d, 3H); MS (ESI) for C19H27N04: 334.1965 (MH+). The free base was dissolved in 4M hydrochloride in 2-propanol. The mixture was concentrated to afford product as hydrochloride salt.

Statistics shows that 54149-17-6 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-2-(2-methoxyethoxy)ethane.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT.LTD.; NEKTAR THERAPEUTICS (Incorporated under the Laws of Delaware and domiclled in the State of California); DUARTE, FRANCO; ANAND, NEEL; SHARMA, PANKAJ; SINGH, DEVENDRAPRATAP U.; WO2015/79459; (2015); A1;,
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946-80-5, 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. 946-80-5, name is Benzyl Phenyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 45 mL of the reaction tube were added 0.5 mmol of benzyl phenyl ether, 0.25 mmol of I2, 1.5 mL of acetonitrile solution of nitrosonium tetrafluoroborate (1.5 mL of solution containing 0.1 mmol of nitrosonium tetrafluoroborate), a sealed reaction tube , The temperature was controlled at 30 C, and the reaction was carried out under magnetic stirring for 5 hours, followed by cooling the reaction system to room temperature. The reaction mixture was purified by column chromatography to give 4-benzyloxyiodobenzene with an isolation yield of 60%. The structure of the product was determined using 1H-NMR, 13C-NMR, and GC-MS, see Figures 15-17

The synthetic route of 946-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
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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. 929-75-9

General procedure: A mixture of cinnamic acid (6.30 mmol), EDCI (7.50 mmol), DMAP (0.60 mmol), and anhydrous dichloromethane (20 mL) was stirred to dissolve, then diamino-ether (3 mmol) was added and stirred at room temperature for 12 h. Then, the solid was filtered off, the filtrate was added with H2O (50 mL) and extracted by dichloromethane three times. The combined organic layers were washed with H2O and brine, dried with anhydrous sodium sulfate for 8 h, filtered, and evaporated. The resulting residue was purified by preparative TLC with petroleum ether/ethyl acetate = 2:1-1:1 to give pale white solid or light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 929-75-9, its application will become more common.

Reference:
Article; Wang, Jiawen; Hong, Ge; Li, Guoliang; Wang, Wenzhi; Liu, Tianjun; Molecules; vol. 24; 24; (2019);,
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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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., 3616-56-6

Synthesis example B17: Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17); (1 7); Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux. Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h. The mixture is cooled to room temperature and diluted with methylene chloride. In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCI solution. The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1 .35 g of product (27.3percent yield).1 H N MR (CD2CI2; 400 MHz): “5 = 8.73 (s, 1 H), 8.17 (s, 1 H), 8.16 (d, 1 H), 8.08 (d, 1 H), 7.78 (d, 1 H), 7.60 (d, 1 H), 7.56 (m, 2H), 7.49 (dd, 1 H), 7.31 (dd, 1 H).

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; BASF SE; BASF (CHINA) COMPANY LIMITED; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH; LANGER, Nicolle; SCHILDKNECHT, Christian; WATANABE, Soichi; FUCHS, Evelyn; WAGENBLAST, Gerhard; LENNARTZ, Christian; MOLT, Oliver; DORMANN, Korinna; HUNZE, Arvid; KRAUSE, Ralf; SCHMID, Guenter; HEUSER, Karsten; VAN ELSBERGEN, Volker; BOERNER, Herbert Friedrich; WO2011/125020; (2011); A1;,
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29578-83-4, A common compound: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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.

). 1-Bromo-3-methoxy-5-methylbenzene (1.00 g, 5.0mmol) and pyridine/H2O (2:5, 30 mL) were added to a round-bottomflask, followed by KMnO4 (3.14 g, 20 mmol). The resulting mixturewas then heated while refluxing for 48 hr. After the removal of the precipitateby filtration, 2 M HCl was added to the reaction mixture to acidify it (pH 2).The aqueous phase was extracted with ethyl acetate. The organic phase waswashed with brine and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure and the residue was purified usingsilica gel column chromatography. The white solid (385 mg, 34% yield) wasidentified as 3-bromo-5-methoxybenzoic acid (3a) on the basis of 1H-NMR spectra. 1H-NMR(400 MHz, CDCl3): d3.86(s, -OCH3, 3H), 7.29 (t, J=2.0Hz, Ar H, 1H), 7.54 (t, J=2.0 Hz, ArH, 1H), 7.83 (t, J=2.0 Hz, Ar H, 1H).

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-Bromo-3-methoxy-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ohe, Tomoyuki; Umezawa, Ryutaro; Kitagawara, Yumina; Yasuda, Daisuke; Takahashi, Kyoko; Nakamura, Shigeo; Abe, Akiko; Sekine, Shuichi; Ito, Kousei; Okunushi, Kentaro; Morio, Hanae; Furihata, Tomomi; Anzai, Naohiko; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3708 – 3711;,
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Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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. 1484-26-0

A mixture of triethyl orthoformate (92 milliliters (mL), 0.55 mole (mol)) and 2,2-dimethyl-[1,3]-dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at 55¡ã C. for 90 minutes and then cooled to 45¡ã C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period of 45 minutes while maintaining the reaction temperature below 50¡ã C. The reaction was then heated at 45¡ã C. for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1¡ã C., and the product was isolated by filtration and washed with cold ethanol (400 mL) until the filtrate was colorless. 5-{[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (170.65 g) was isolated as a tan, powdery solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1484-26-0, its application will become more common.

Reference:
Patent; Zarraga, Isidro Angelo E.; US2007/166384; (2007); A1;,
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