Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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 54149-17-6, category: ethers-buliding-blocks

Aniline (1.61g, 17.3mmol), potassium carbonate (9.56g, 69.2mmol), potassium iodide (1.43g,8.65mmol) and 1bromo2(2methoxyethoxy)ethane (9 .50g, was suspended 51.9 mmol) in dry DMF (5.0mL), it washeated at 80 C 24 hours. After allowed to cool to room temperature, ethyl acetate (200 mL) was added and the aqueouswas washed successively with saturated brine. The organic phase was dried over anhydrous magnesium sulfate, and thefiltrate was concentrated under reduced pressure. Crude was purified by silica gel column chromatography to give 4.27g ofcompound 14 as a colorless oily substance. 83% yield.

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

Reference:
Patent; Kyushu University; Shinkai, Seiji; Noguchi, Takao; (37 pag.)JP2016/196447; (2016); A;,
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Electric Literature of 946-80-5,Some common heterocyclic compound, 946-80-5, name is Benzyl Phenyl Ether, molecular formula is C13H12O, 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.

General procedure: To a 10 mL sealed tubewas added anisole (108 mg, 1.0 mmol), aceticanhydride (204 mg, 2.0 mmol) and catalyst (2.5 mol%). Then the mixture wasstirred at room temperature until complete consumption of starting material asmonitored by TLC or GC-MS analysis. Then the reaction mixture was evaporated invacuum, and CH2Cl2 (3¡Á10 ml) was added to the reactionmixture. The catalyst was then filtered out for the next cycle of reaction. Thecombined CH2Cl2 solution was removed by evaporation invacuum and was then subject to silica gel column chromatograph.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzyl Phenyl Ether, its application will become more common.

Reference:
Article; Zhang, Xiaohong; Xu, Xinhua; Li, Ningbo; Liang, Zhiwu; Tang, Zilong; Tetrahedron; vol. 74; 15; (2018); p. 1926 – 1932;,
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Related Products of 171290-52-1, These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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.

In a 25 ml round bottom flask, 9 mg of copper acetate,18mg 1,10-phenanthroline, 276mg potassium carbonate, 325mgN-allyl-N- (6-chlorohexynyl) p-toluenesulfonamide, 486mg of 3,5-dimethoxyphenylacetylene, 5mL of toluene,Then heated to 100 C for 12h, and then filtered to obtain 6-allyl-7-((3,5-dimethoxyphenyl) ethynyl) -1-p-toluenesulfonyl-2,3,4 Crude product of 5,5-tetrahydro-1H-azepineThe crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 20: 1).Get6-allyl-7-((3,5-dimethoxyphenyl) ethynyl) -1-p-toluenesulfonyl-2,3,4,5-tetrahydro-1H-azepine Pure302 mg, yield 67%.

Statistics shows that 3,5-Dimethoxyphenylacetylene is playing an increasingly important role. we look forward to future research findings about 171290-52-1.

Reference:
Patent; The Chinese People’s Liberation Army National Defense University Of Science And Technology; Yang Xuheng; Huang Jian; Wang Fang; Li Yujiao; Wang Jianfang; Tao Chengan; Zou Xiaorong; Song Chenchao; (30 pag.)CN110627722; (2019); 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 52189-63-6 as follows. Application In Synthesis of 1-Fluoro-3,5-dimethoxybenzene

EXAMPLE 12 Method of Forming a 1-(2,6-dimethoxy-4-fluorophenyl)-2-methylpropan-1-one Intermediate to a Photoinitiator of the Present Invention The following reaction was carried out as detailed below: Into a 1-liter, three-necked round-bottom flask was placed 20.0 g (0.13 mole) of 1,3-dimethoxy-5-fluorobenzene, 13.6 g (0.0.13 mole) of 2-methylpropanoyl chloride, and 100 ml of nitrobenzene. The mixture was flushed with argon and an equal molar amount of AlCl3 (17.2 g) was added to the reaction mixture while stirring at 5C. The mixture was stirred at a temperature of 5C for about 1 hour after the addition of the AlCl3. The reaction mixture was then mixed with about 100 ml of distilled water and extracted with dichloromethane. The organic layer was washed with NaHCO3 solution, salt water, and then dried. The solvent was removed by vacuum to yield the final productproduct, 1-(2,6-dimethoxy-4-fluorophenyl)-2-methylpropan-1-one. The yield of the reaction was 22.8 g of product (77%).

According to the analysis of related databases, 52189-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIMBERLY-CLARK WORLDWIDE, INC.; EP1117698; (2006); B1;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H10O2

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in a compound 7b (76.7 mg, 300 mumol), -3,5- dimethoxybenzene (121 mg 1-ethynyl, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. The reaction mixture was stirred at room temperature for 48 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) Compound 2b was obtained by using as a brown solid (90.6mg, 73%).

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; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., SDS of cas: 6298-96-0

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (5.65 ml, 38.1 mmol 1.0 equiv.), 1-(pyridin-2-yl)ethanone (4.49 ml, 40 mmol, 1.05 equiv.), DCE (Volume: 38.1 ml, 1.0M) and STAB-H (16.15 g, 76 mmol, 2.0 equiv.) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4, filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% EtOAc in hexanes over 40 min). The fractions were concentrated to a clear oil which solidified upon standing. (S)-1-(4-methoxyphenyl)-N-((S)-1-(pyridin-2- yl)ethyl)ethanamine (3.86 g, 15.06 mmol, 40 % yield). 1H NMR (400 MHz, CDCl3): delta = 8.60 (d, J= 5.2 Hz, 1H), 7.61 (dt, J= 7.6, 1.8 Hz, 1H), 7.21-7.12 (m, 1H), 7.13 (d, J= 9.2 Hz, 2H), 7.06 (d, J= 7.2 Hz 1H), 3.80 (s, 3H), 3.57 (q, J= 7.4 Hz, 1H), 3.39 (q, J= 6.9 Hz, 1H), 1.29 (d, J= 6.8 Hz, 3H), 1.26 (d, J= 7.3 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 257.2

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); 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, Safety of 3,5-Dimethoxytoluene

Step 1: Put 1,3-dimethoxy-5-methylbenzene (30g, 0.20mol)And dichloromethane (900 mL) were added to a dry round bottom flask (1 L), and the above solution was added dropwise with dichlorosulfone (52.5 g, 0.40 mol) under ice-cooling,After the addition was complete, the mixture was stirred at room temperature overnight.After completion of the reaction, aqueous NaHCO3 solution was added dropwise to adjust the pH = 8, and dichloromethane was extracted.Wash with dilute hydrochloric acid and distilled water,Dry and concentrate under reduced pressure to obtain compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene(31g, white solid),Used directly in the next step.

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; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wan Huixin; Pan Jianfeng; Ma Jingui; (63 pag.)CN110857300; (2020); A;,
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Synthetic Route of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

(Formula 1-2: methyl 4-(((3-(trifluoromethoxy)phenyl)amino)methyl)benzoate)[1723][1724]Compound ofFormula 1-1(3-(trifluoromethoxy)aniline; 0.385 mL, 4.625 mmol), methyl 4-(bromomethyl)benzoate (1.271 g, 5.550 mmol) and DIPEA (1.228 mL, 6.937 mmol) were dissolved in acetonitrile (5 mL) at room temperature and stirred at the same temperature for 16 hours. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=20percent) to give the desired compound ofFormula 1-2(0.607 g, 40.3percent) in the form of a white solid.

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

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Changsik; YANG, Hyun-Mo; CHOI, Hojin; KIM, Dohoon; KIM, Soyoung; HA, Nina; LIM, Hyojin; KO, Eunhee; YOON, Seongae; BAE, Daekwon; WO2014/178606; (2014); A1;,
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Application of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-(5-amino-4-fluoro-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (1.36 g, 4.28 mmol, 1.00 eq), 4-methoxy-N-methylbenzylamine (0.971 g, 6.42 mmol, 1.50 eq) and DBU (0.960 mL, 6.42 mmol, 1.50 eq) were combined in NMP (20 mL) and heated at 180¡ã C. under Ar overnight. The mixture was cooled to RT and poured onto H2O (200 mL). The resulting solids were collected by filtration, rinsed very well with H2O, dried on the filter to dampness and then dissolved in EtOAc. The solution was dried (MgSO4), filtered and evaporated to afford 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (1.86 g, 100percent yield) as a brittle brown foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): delta 8.45 (s, 1H), 7.63 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 6.86-6.82 (m, 1H), 6.57 (d, J=9.6 Hz, 1H), 6.29 (s, 1H), 4.88 (br s, 2H), 4.85 (s, 2H), 3.69 (s, 3H), 3.52 (s, 3H), 3.07 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 433.3 [M+H]+.

The synthetic route of 4-Methoxy-N-methylbenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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538-86-3, name is (Methoxymethyl)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. HPLC of Formula: C8H10O

General procedure: A mixture of nitriles (5 mmol), methyl ethers (6 mmol) and Fe(ClO4)3¡¤H2O (5percentmol) was placed in a round bottom flask. Then the reaction mixture was heated at 100 ¡ãC for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 10 ml water was added into reaction system and extracted with ethyl acetate (3 ¡Á 20 ml). The organic layers were collected, combined, washed with water (3 ¡Á 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure products (1a?1k and 2a?2p) were obtained by directly passing through a silica gel (200?300 mesh) column using petroleum ether/ethyl acetate (10:1?5:1).

The synthetic route of 538-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of the Iranian Chemical Society; vol. 16; 6; (2019); p. 1355 – 1363;,
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