Tag: M.W=100-200

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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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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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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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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A common compound: 1484-26-0, name is 3-Benzyloxyaniline, 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. 1484-26-0

General procedure: BSB-Cl 2 (314 mg, 1.2 mmol) and aniline 1 (1mmol) were premixed in THF (10 ml) at0 C to which was added LiHMDS (2 ml, 2 mmol). The resulting mixture was stirred for2 h at this temperature. Upon reaction completion, the solution was concentrated. Theresidue was purified with basic alumina flash chromatography to afford pure product

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, 1484-26-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lu, Erhu; Yadav, Arun; Weaver, Donald F.; Reed, Mark A.; Synlett; vol. 24; 17; (2013); p. 2259 – 2262;,
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60792-79-2, 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 60792-79-2 as follows.

In a typical run, sodium hydroxide (400 mg, 10 mmol) is dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) is added. The resulting reaction mixture is stirred at room temperature for 30 min. A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) is then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture is stirred at room temperature for 18 h. It is then concentrated under reduced pressure. The resulting residue is taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate.

According to the analysis of related databases, 2,2′-Oxybis(ethylamine) dihydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2012/252810; (2012); A1;,
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22236-08-4, 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 22236-08-4 as follows.

Reference Example 353-{[3-(Difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione To a solution of 3-(difluoromethoxy)aniline (1000 mg, 6.25 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (518 mg, 7.50 mmol) in 4 mL of water was added dropwise at 0 C., and the mixture was stirred at 0 C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (1538 mg, 18.75 mmol) and acetylacetone (812 mg, 8.12 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-{[3-(difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione (1500 mg, 89%).LCMS: m/z=271 [M++H].

According to the analysis of related databases, 3-(Difluoromethoxy)aniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taniguchi, Takahiko; Kawada, Akira; Kondo, Mitsuyo; Quinn, John F.; Kunitomo, Jun; Yoshikawa, Masato; Fushimi, Makoto; US2010/197651; (2010); A1;,
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