Month: November 2020

54314-84-0, name is ((3-Bromopropoxy)methyl)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. Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; WASHIO, Yoshiaki; (112 pag.)WO2019/3141; (2019); A1;,
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5961-59-1, The chemical industry reduces the impact on the environment during synthesis 5961-59-1, name is 4-Methoxy-N-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 2,4-Dichloropyrimidine (1) (0.149g, 1.0 mmol) in 15 mL isopropanol was added 4-methoxy-N-methylaniline derivative (2) (1.0 mmol). The reaction mixture was stirred at room temperature and monitored by TLC. When the reaction was completed, the solvent was removed under vacuum and the slurry was dilute with water (10 mL). The solution was adjusted to pH 9 with a saturated NaHCO3 solution, extracted with ethyl acetate (10 mL¡Á3) for three times, the organic phase was washed with water (10 mL), dried over sodium sulfate, concentrated and purified by column chromatography to give the target compound 3a-3b. 2-Chloro-N-(4-methoxyphenyl)-N-methylpyrimidin-4-amine (3a) White solid. Yield: 79percent. 1H NMR (400 MHz, Chloroform-d) delta 7.85 (d, J = 6.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H), 7.12 (d, J = 2.3 Hz, 1H), 6.99 (d, J = 2.3 Hz, 1H), 6.97 (d, J = 2.2 Hz, 1H), 6.08 (d, J = 6.1 Hz, 1H), 3.85 (s, 3H), 3.44 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 163.86, 160.66, 158.97, 155.98, 136.25, 128.03, 115.50, 103.27, 55.55, 38.35. HRMS (ESI) (m /z) [M+H]+ calcd for C12H12N3OCl, 250.0742; found, 250.0725. Purity: 100.0percent (by HPLC).

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

Reference:
Article; Xu, Shaoyu; An, Baijiao; Li, Yuxin; Luo, Xunbang; Li, Xingshu; Jia, Xian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1769 – 1775;,
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1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

According to Scheme 8, hydroxylamine sulfate (18 g, 3 equivalents) was dissolved in water (80 mL) and then chloral hydrate (7.3 g, 1.2 equivalents) was added. After 15 min, a solution of the starting aniline (5.0 mL, 37 mmol), dissolved in 1 N HCl (44 mL, 1.2 equivalents), was added dropwise (20 min) to the reaction mixture. The resulting cloudy mixture was heated at 80 C. for 1 h, cooled to rt, and diluted with CHCl3 (160 mL). The aqueous layer was extracted with CHCl3 (2¡Á80 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated. Hexanes (40 mL) were added. Evaporation of the solvent provided crude product which was used in the next step without further purification: MS(ESI): 247 (M-H)-.

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; Icagen, Inc.; US2005/59823; (2005); A1;,
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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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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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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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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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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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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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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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