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. 2944-49-2, name is 1-Methoxy-2,3-dimethylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2944-49-2

(0464) 1-Methoxy-2,3-dimethylbenzene (13.6 g, 100 mmol), NBS (39.2 g, 220 mmol) and benzoperoxide (242 mg, 1 mmol) were dissolved in carbon tetrachloride (200 mL). The mixture was heated to 90 C. and reacted for 12 h. After the reaction, the mixture was cooled to room temperature, and filtrated. The filtrate was concentrated to get the title compound as a crude product (30 g).

The synthetic route of 2944-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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6346-09-4, Adding some certain compound to certain chemical reactions, such as: 6346-09-4, name is 4,4-Diethoxybutan-1-amine, 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 6346-09-4.

Procedure 10: Protection of Amine by Fmoc GroupTo a stirring solution of the amine (0.049 mol) in DCM (100 mL), was added DIPEA (16 mL, 0.099 mol) and the reaction mixture was cooled to 0C. Fmoc- Cl (12.8 g, 0.049 mol) was then added portion- wise over several minutes, and the reaction was allowed to warm to room temperature for 2 hr. The organic layer was washed with water (2 x 50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to dryness to yield the Fmoc protected amine (90-95% yield).; N-Fmoc-4-amino-butyraldehyde diethyl acetal 4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.

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 6346-09-4.

Reference:
Patent; ACHAOGEN, INC.; AGGEN, James Bradley; GOLDBLUM, Adam Aaron; DOZZO, Paola; HILDEBRANDT, Darin James; KANE, Timothy Robert; GLIEDT, Micah James; LINSELL, Martin Sheringham; WO2011/44503; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 103-50-4, name is Benzyl ether, molecular formula is C14H14O, 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. 103-50-4

General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103-50-4, its application will become more common.

Reference:
Article; Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun; Heterocycles; vol. 94; 1; (2017); p. 86 – 94;,
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Adding some certain compound to certain chemical reactions, such as: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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 60792-79-2. 60792-79-2

EXAMPLE 31 2,2′-[Oxybis(ethanediyldiimino)]bis(1,2-diphenylethanol). A mixture of trans-stilbene oxide (2.21 g, 0.0113 mol), 2-(2-aminoethoxy)ethylamine dihydrochloride (1 g, 0.00565 mol) and sodium bicarbonate (0.95 g, 0.0113 mol) were stirred together in n-butanol (10 mL) and heated on a steam bath for 16 hours. Upon cooling a solid formed. The mixture was triturated with methanol (25 mL) and the mixture then diluted with water (200 mL). The solid was collected and dried under ambient conditions on absorbent paper for 2 hours. The solid still had a strong odor of 1-butanol. The solid was heated in boiling toluene (50 mL) and isooctane (25 mL) added to the boiling solution. The organic layer was decanted from a small amount of a denser second layer, presumably water. Upon cooling, the product crystallized from the toluene-isooctane mixture. The solid was collected and dried under ambient conditions for 18 hours to obtain 2.05 g (92% yield); mp 161-164 C. Analysis: Calculated for C32 H36 N2 O3: C, 77.39; H, 7.31; N, 5.64 Found: C, 77.40; H, 7.32; N, 5.77

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 2,2′-Oxybis(ethylamine) dihydrochloride.

Reference:
Patent; A. H. Robins Company, Incorporated; US5171753; (1992); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

458-50-4, A common compound: 458-50-4, name is 4-Bromo-3-fluoroanisole, 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.

General procedure: To a solution of 2-bromo-4-fluorobenzonitrile (0.30 g, 1.5 mmol) and cyclopropanol (0.14 g, 2.4 mmol) in DMF (4 mL) wasadded Cs2CO3 (0.88 g, 2.7 mmol) in a 25 mL single-necked round-bottom flask. After that, themixture was stirred at 25 ¡ãC under nitrogen. After stirring for 4 h, the resulting mixture was dilutedwith H2O (30 mL) and extracted with MTBE (10 mL¡Á3). Then the combined organic phase waswashed with saturated aqueous NaCl (10 mL¡Á3) and dried over Na2SO4 for 0.5 h. After that, theorganic phase was filtered under reduced pressure and the filtrate was concentrated underreduced pressure to give product as a yellow sticky substance. Then a mixture of 30 mL MTBE and100 mL n-hexane was added to dissolve the yellow sticky substance. Subsequently, the solutionwas cooled for 30 minutes with the mixture of water and ethanol. Lastly, the solution was filteredunder reduced pressure and the filtrate was dried naturally to obtain desired product in 80.3percentyield (0.29g).

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, 4-Bromo-3-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Hao; Gao, Zhuo; Zhou, Shaodong; Qian, Chao; Synlett; vol. 30; 8; (2019); p. 982 – 986;,
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702-24-9, Adding a certain compound to certain chemical reactions, such as: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 702-24-9.

A solution of Example A18 (22 g, 65.7 mmol), (4-methoxy-benzyl)-methyl-amine (14.9 g, 98.5 mmol) and DBU (15 g, 98.5 mmol) in NMP (120 mL) was heated at 160¡ã C. for 5 h. The mixture was poured into 200 mL of water while stirring and the resulting solids were collected by filtration, washed with water, dried and then washed with Et2O to give 3-(5-amino-2,4-difluoro-phenyl)-1-ethyl-7-[4-methoxy-benzyl)-methyl-amino]-1H-[1,6]naphthyridin-2-one (25 g, yield 85percent yield). 1H NMR (300 MHz, DMSO-d6): delta 8.51 (s, 1H), 7.80 (s, 1H), 7.19-7.17 (d, J=8.7 Hz, 2H), 7.06 (t, J=10.2 Hz, 1H), 6.90-6.81 (m, 3H), 6.32 (s, 1H), 5.02 (s, 2H), 4.86 (s, 2H), 4.19 (q, J=6.9 Hz, 2H), 3.72 (s, 3H), 3.14 (s, 3H), 1.14 (t, J=6.9 Hz, 3H); MS (ESI): m/z 451.1 [M+H]+.

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 20781-20-8 name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

(h) (2R,5R)-tert-butyl 2-(1-bromo-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-3-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)morpholine-4-carboxylate (2R,5R)-tert-butyl 2-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-5-(((tert-butyl diphenylsilyl)oxy)methyl)morpholine-4-carboxylate (0.5 g, 0.729 mmol), (2,4-dimethoxyphenyl)methanamine (0.25 g, 1.46 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.283 g, 2.186 mmol) were dissolved in 20 mL 1,4-dioxane stirred at r.t for overnight. Another 1 equiv. of (2,4-dimethoxyphenyl)methanamine was added and heated to 50 C. and stirred for one more overnight. The reaction mixture was then concentrated under vacuum to give the crude (2R,5R)-tert-butyl 2-(1-bromo-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-3-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)morpholine-4-carboxylate (0.516 g, 87%). LCMS: [M+H]+: 818.31, Ret. time 1.28 min, LC-MS method E).

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

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Ether – Wikipedia,
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32338-02-6, 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. 32338-02-6 name is 2-Bromo-4-methoxyaniline, 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.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

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

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-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 103291-07-2, 103291-07-2

4-Bromo-1-fluoro-2-methoxybenzene a15 (0.0204 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated under a 6W blue light lamp at 50 C for 72 h.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 30/1.Yellow liquid (32) (0.0109 g, 94%) was obtained.

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, 4-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20265-97-8, The chemical industry reduces the impact on the environment during synthesis 20265-97-8, name is 4-Methoxyaniline hydrochloride, I believe this compound will play a more active role in future production and life.

p-Anisidine hydrochloride (23.14 g, 132.5 mmol) was dissolved in ethanol (400 mL) and TRIFLUOROACETALDEHYDE ethyl hemiacetal (20 mL, 172.3 mmol) was added and refluxed overnight. The reaction was concentrated, and the crude compound was redissolved in N, N-dimethylformamide (150 mL) and cooled to 0C. N-BROMOSUCCINIMIDE (23.59 g, 132.5 mmol) was added to the solution over five minutes. The reaction was warmed to rt and stirred overnight. The reaction was quenched with water (1000 mL) and ethyl acetate (5000 mL), extracted with ethyl ACETATE (3X500 ML), WASHED WITH brine (1×500 ML) 7 DRIED OVER NA2804, concentrated, and purified by flash chromatography using 0-10% ethyl acetate/hexanes as eluent afforded 18. 8 g (48%) of the hydrazone intermediate

The chemical industry reduces the impact on the environment during synthesis 4-Methoxyaniline hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRYSTOL-MYERS SQUIBB COMPANY; WO2004/83177; (2004); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem