Category: ethers-buliding-blocks

52189-63-6, Adding some certain compound to certain chemical reactions, such as: 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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 52189-63-6.

Boron tribromide (1 M in dichloromethane, 9mL, 89.985mmol) was added drop wise to an ice- cooled solution of 3,5-dimethoxy fluorobenzene (3ml, 22,496mmol) in dichloromethane (2OmL) and the mixture was stirred at O0C to room temperature for 4 hours. The solution was cooled to O0C, further boron tribromide (4ml, 44.992mmol) was added and stirring continued, warming to room temperature for an additional 18 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 90 minutes. The organic layer was separated and extracted with 2N sodium hydroxide (30ml), which was then acidified to pH1 by drop wise addition of concentrated hydrochloric acid. The aqueous layer was then re- extracted with dichloromethane (3x15mL), the combined organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 54% yield, 1.72g. 1HNMR(400MHz, CD3OD) delta: 3.72(s, 3H), 6.07-6.15(m, 3H)

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 52189-63-6.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
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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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., 111-95-5

(1)N’5′-[2-Chloro-4-(trifluoromethyl)phenyl]-N’5′-ethyl-2-(4-methoxybenzyl)-N’7′,N’7-bis(2-methoxyethyl)-2H-pyrazolo[4,3-d]pyrimidine-5,7-amine A mixture of 7-chloro-N-[2-chloro-4-(trifluoromethyl)phenyl]-N-ethyl-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-d]pyrimidine-5-amine(a compound obtained in Reference Example 16) (75 mg), N,N-diisopropylethylamine(18.2 mg) and bis(2-methoxyethyl)amine(93.7 mg) in N-methylpyrrolidone(1.1 mL) was stirred at outside temperature of 110C under argon gas atmosphere overnight. After being cooled to room temperature, water and chloroform were added to the reaction mixture, the separated organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulted residue was purified by using a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:2) to give the titled compound(84.3 mg) quantitatively as a pale yellow liquid. MS(APCI)m/z:593/595[M+H]+.

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Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP1903045; (2008); A1;,
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A common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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. 6346-09-4.

Synthesis of phthalimide lb.; To a stirred solution of 4-aminobutyraldehyde diethyl acetal la (89.3 mmol) in CH3CN (100 mL) was added N-carbethoxyphthalimide (93.8 mmol). Once the reaction was complete, the acetonitrile was removed under reduced pressure and the aqueous phase extracted with EtOAc (x3). The organic phase were combined, then washed with water (x4), saturated brine (x3), then dried (Na2S04), filtered, and evaporated under reduced pressure to give the title compound lb, which crystallized on standing.

The synthetic route of 4,4-Diethoxybutan-1-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2005/70930; (2005); A2;,
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A common compound: 494-99-5, name is 1,2-Dimethoxy-4-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. 494-99-5

(EThe compound 1,2-dimethoxy-4-methyl-benzene [25 g (0.164 mol)] was added to a mixture of POCl3 [151 g (0.987 mol)] and DMF [73 g (1 mol)] with stirring at 0 C. The viscous mixture was then heated to 80 C. and stirred there for 4 h. The reaction mix was then poured onto ice and then extracted with Et2O. The extract was dried (MgSO4) and the solvent removed. Flash chrom. with 10% EtOAc/Hexane afforded the desired aldehyde [26 g (0.144 mol)] 88% yield. A mixture of the above aldehyde [5.4 g (0.03 mol)], malonic acid [6.24 g (0.06 mol)], pyridine (20 mL) and piperidine (0.5 mL) was stirred at 80 C. for 1 h followed by stirring for 3 h at 115 C. The reaction was then poured into water (200 mL) and acidified with conc. HCl. The resulting white ppt. was filtered and vacuum dried. Yield=4.8 g (63% overall) MS (m/z): 223 [M+H]

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, 494-99-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Prosetta Antiviral, Inc.; ATUEGBU, Andy; SOLAS, Dennis; HURT, Clarence R.; KITAYGORODSKYY, Anatoliy; (141 pag.)US2016/168100; (2016); A1;,
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These common heterocyclic compound, 34967-24-3, name is 3,5-Dimethoxybenzyl amine, 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. 34967-24-3

To a solution of 3, 5-dimethoxybenzylamine (2.5 g, 15.0 mmol) in 2-butanone (22 mL) was added 1,3-propane sultone (1.95 g, 15.8 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2 x 25 mL), and dried in vacuo. This allowed the isolation of compound BA, 2. 89 g (67%).

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 34967-24-3.

Reference:
Patent; NEUROCHEM (INTERNATIONAL) LIMITED; WO2004/113275; (2004); A2;,
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6346-09-4, name is 4,4-Diethoxybutan-1-amine, 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. Patent; CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; AMARI, Gabriele; BIAGETTI, Matteo; LINNEY, Ian; WO2012/168359; (2012); A1;,
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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 366-99-4 as follows. 366-99-4

To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at approximately -10 to -20 C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of N,N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for an hour. The reaction mixture was then allowed to reach room temperature for an hour. The second step was continued without further purification. Cycloheptylamine (0.25 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at rt. The third step was also preceded without any further purification. S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure affording 0.920 g crude material. The crude material was purified by column chromatography to yield a white solid 139 (0.550 g, 60%), mp 75-77 C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 7.9 min, 95.9% purity; MS (ESI): m/z 458 (M+H, 100).

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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A common heterocyclic compound, 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, molecular formula is C17H21NO, 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. 43229-65-8.

Synthesis of 4-benzyloxy-3-methoxymethyl-alpha[N-benzyl-N(alpha-methyl-4-methoxyphenethyl)amino]acetophenone Amounts of 39.5 g of the compound obtained in the step C1 and 57.7 g of N-benzyl-N(alpha-methyl-4-methoxyphenethyl)amine are stirred for 6 hours in 200 ml of acetonitrile. The crystals precipitated are filtered off, and the filtrate is concentrated, to give the object compound. The compound is used for the following step without purification.

The synthetic route of N-Benzyl-1-(4-methoxyphenyl)propan-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US4317930; (1982); A;,
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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. 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, This compound has unique chemical properties. The synthetic route is as follows., 2930-05-4

General procedure: To a mixture of epoxide (1 equiv) and NaN3 (1.5 equiv) in CH3CN-H2O (8:2, 10 mL) Montmorillonite K 10 (5% w/w) was added. The reaction mixture was stirred at 80C for a specified time as required to complete the reaction. After completion as indicated by TLC, the reaction mixture was then filtered, the filter pad was washed with CH3CN and the combined filtrates were evaporated. The reaction mixture was extracted with EtOAc, the combined organic layers were washed with H2O and brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude product was then purified by column chromatography over silica gel using EtOAc/petroleum ether as eluent to provide the pure azido alcohol. Characterization data of all the products are shown below.

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:
Article; Ch Ghosh, Keshab; Banerjee, Isita; Sinha, Surajit; Synthetic Communications; vol. 48; 22; (2018); p. 2923 – 2934;,
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1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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.

General procedure: To a solution of amine (1 mmol) in 3 mL of pyridine at 0¡ãC was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25¡ãC. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.

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 1484-26-0.

Reference:
Article; Kril, Liliia M.; Vilchez, Valery; Jiang, Jieyun; Turcios, Lilia; Chen, Changguo; Sviripa, Vitaliy M.; Zhang, Wen; Liu, Chunming; Spear, Brett; Watt, David S.; Gedaly, Roberto; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3897 – 3899;,
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