Month: March 2021

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 64465-53-8,Some common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-methoxyaniline, molecular formula is C7H8FNO, 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.

Intermediate 28 (0.050g) was suspended in acetonitrile (2ML), 4-fluoro-3-(methyloxy)aniline (0.025g) (available from Aldrich) was added and the mixture heated at 80C for 16h. The mixture was cooled to room temperature and the solvent blown off under a stream of nitrogen. Purification by mass directed HPLC gave a yellow oil. This was loaded onto an SPE cartridge (1G Varian Bond Elut, aminopropyl solid phase) and eluted with methanol to give the title compound as a yellow solid (0. 018G). LC/MS Rt 2.58min M/Z 475 [MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-3-methoxyaniline, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/30212; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 588-63-6, name is (3-Bromopropoxy)benzene, 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 588-63-6, COA of Formula: C9H11BrO

EXAMPLE 15 3-(Octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester A mixture of 12 g (0.024 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 6 ml (0.038 mol) of 3-phenoxypropyl bromide, 3.6 g (0.024 mol) of sodium iodide and 10 g (0.072 mol) of potassium carbonate in 400 ml of acetone and 80 ml of DMF was stirred at reflux for 46 hours. The reaction mixture was filtered and the filtrate was concentrated to dryness at reduced pressure. Water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to an oil which was purified by HPLC using 5percent ethyl acetate-hexane. The pure fractions were combined, triturated with hexane and filtered to give 14.6 g (96percent yield, mp 46¡ã-47¡ã) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra. Anal. Calcd for C41 H58 O5: C, 78.05; H, 9.27. Found: C, 77.89; H, 9.03.

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; Hoffmann-La Roche Inc.; US5298652; (1994); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1663-61-2, 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. 1663-61-2, name is (Triethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

The synthetic route of (Triethoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

The compound obtained in Reference Example 1-2 (19mg) and 4-isopropoxyaniline (10mg) was dissolved in acetonitrile (1.5 mL). And reacted for 10 minutes at the microwave irradiation under 180 C. After the solvent was concentrated to give the title compound purified by silica gel column chromatography (17mg, 60%).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, A new synthetic method of this compound is introduced below., Product Details of 204452-91-5

[0578] Into a 3 I 4-necked round-bottom flask was placed7 -( dimethoxymethyl)-1 ,2,3,4-tetrahydro-1 ,8-naphthyridine(intermediate 4, 114.6 g, 550.3 mmol) in acetonitrile (2 1).This was followed by the addition of NBS (1 03 g, 578 mol) inportions with stirring at 25 C. The resulting solution wasstirred for 30 min at 25 C. The resulting mixture was concentratedunder vacuum and the residue was diluted with1000 ml of diethylether. The mixture was washed with 3xl 00ml of ice/water. The aqueous phase was extracted with 2xl 00ml of diethylether and the organic layers were combined. Theresulting mixture was washed with lxlOO ml of brine, driedover sodium sulfate and concentrated under vacuum to givethe title compound as a light yellow solid. LC-MS: (ES, m/z):[0579] 286.03 [M+Ht. 1H-NMR: (300 MHz, CDCI3 ) o1.86-1.94 (2H, m), 2.70-2.74 (2H, m), 3.9-3.43 (2H, m), 3.47(6H, s), 5.23 (lH, s), 5.58 (lH, s), 7.29 (lH, s).

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; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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 asolution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (e, 1.0 g 3.52 mmol) in ethanol (20 mL) was addedsubstituted aromatic amine (3.52 mmol) and acetic acid (1 drop). Themixture was refluxed for 3 h. Thereafter, the mixture was cooled toroom temperature, the precipitate was formed and filtered, washedwith ethanol and dried under reduced pressure to afford product l1-l14

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.

Reference:
Article; Chen, Shaowei; Han, Yufei; Hou, Yunlei; Wang, Ruxin; Yan, Pingzhen; Ye, Tianyu; Zhao, Yanfang; Bioorganic Chemistry; vol. 99; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Safety of Perfluoro(2-methyl-3-oxahexanoyl) fluoride

Into a flask under a nitrogen gas atmosphere, 26 g of the compound (62) and 100 g of R225 were introduced. With cooling with ice, 91 g of the compound represented by Rf2-C(O)F was dropwise added thereto while stirring inside of the flask. Inside of the flask was further stirred, and then, the content was concentrated and filtrated to obtain 88 g of compound (52).

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; Asahi Glass Company, Limited; EP2039672; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 332-48-9, A common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

EXAMPLE 103 4-Benzyl-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR139 From a mixture of 4-benzylpiperidine (500 mg, 2.85 mmol), 2-(4-fluorophenoxy)ethyl bromide (655 mg, 2.99 mmol) and K2 CO3 (413 mg, 2.99 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (395 g, 79%): mp 165-167 C., 1 H NMR (CDCl3) 1.70-1.90 (m, 3H), 1.94-2.14 (m, 2H), 2.59 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.50 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.49 (t, J=4.5 Hz, 2H), 6.76-7.30 (m, 9H), 12.47 (bs, 1H); Anal. Calcd for C20 H25 ClFNO: C, 68.66; H, 7.20; N, 4.00. Found: C, 68.66; H, 7.11; N, 3.98.

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; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem