Category: ethers-buliding-blocks

Reference of 216067-66-2, The chemical industry reduces the impact on the environment during synthesis 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, I believe this compound will play a more active role in future production and life.

Example 5 5-(N-Benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-hydroxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione To a solution of the compound obtained in Reference Example 6 (2.0 g, 3.36 mmol) in dichloromethane (40 ml) was added triethylamine (0.94 ml, 6.73 mmol) with ice-cooling, followed by stirring. Then, N,N’-carbonyldiimidazole (1.09 g, 6.73 mmol) was added to the reaction mixture with ice-cooling. The reaction mixture was allowed to warm to room temperature and was stirred for 24 hours. The reaction mixture was ice-cooled again and O-(2,4-dimethoxybenzyl)hydroxylamine (3.11 g, 16.98 mmol) was added. The reaction mixture was then allowed to return to room temperature and stirred for 19 hours. This reaction mixture was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate solution and the aqueous layer was extracted with chloroform. The extracts were combined, washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. To a solution of the residue in dichloromethane (50 ml) was added trifluoroacetic acid (5 ml), followed by stirring at room temperature for 20 minutes. This reaction mixture was partitioned between chloroform and saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted with chloroform. The extracts were combined, washed with aqueous sodium chloride solution and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel to give white amorphous powder, which was recrystallized from chloroform-ether to give the title compound as white crystals (2.2 g, 100%). mp: 164-165 C.; 1H-NMR (300 MHz, CDCl3) delta: 2.05 (3H, s), 3.46 (2H, s), 3.92 (2H, s), 5.35 (2H, s), 6.65(1H, br), 6.90 (2H, t, J=8.0 Hz), 7.28-7.65 (15H, m), 8.04 (1H, s), 9.73 (1H, br). IR (KBr): 3326, 2856, 1715, 1665, 1628, 1591, 1531, 1468 cm-1. FAB-Mass m/z 654(MH)+.

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, O-(2,4-Dimethoxybenzyl)hydroxylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6297379; (2001); B1;,
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Some common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, molecular formula is C13H11BrO, 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. HPLC of Formula: C13H11BrO

.2 eq BuLi in hexane,1.2 eq TMEDA, 8 eq SO2 in Et2O, 3 eq N-chlorosuccinimide, EtjO, -75 C to 25 C, then dioxane, aq NH3. 250C1 16 hA solution of l-benzyloxy-3-bromobenzene (28.3 g) in Et2O (375 mL) is cooled to – 70 C and treated with TMEDA (19.2 mL) and tt-BuLi in hexane (1.6 M, 79 mL). The solution is stirred at -70 C for 1 h and transferred into a cooled solution (-70 0C) of SO2 (54.4 g) in Et2O (375 mL). The mixture is kept at -700C for 15 minutes, then allowed to warm to RT over 1 h. The solvent is evaporated and the residue is suspended in aqueous sodium phosphate (IM, 750 mL, pH 6). EtOAc (500 mL) is added and the solution is cooled to 00C. JV-Chlorosuccinimide (43.5 g) is slowly added and the pH is readjusted to pH 6 by addition OfNa3PO4. The reaction mixture is stirred vigorously for 1 h. The phases are separated and the aqueous phase is extracted twice with EtOAc. The combined organic phases are washed with H2O and brine, dried and concentrated to give a yellowish oil. The residue is taken up in dioxane (400 mL) and NH3 in H2O (28%, 200 mL) is added. The reaction mixture is stirred for 12 h and then concentrated to dryness. The residue is chromatographed on SiO2 gel (eluent hexanes/EtOAc 4:1 to 3:7) to give 3-benzyloxy- benzenesulfonamide as a white powder. API-MS: M-I ?= 262.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53087-13-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2007/120595; (2007); A2;,
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Synthetic Route of 6358-77-6, The chemical industry reduces the impact on the environment during synthesis 6358-77-6, name is 5-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

Step 1: water (5 mL), boric acid (55 mg, 0.89 mmol) and glycerol (2-3 drops) were added to a stirred solution of 5-bromo-2-methoxyaniline (600 mg, 2.97 mmol) and divinylsulfone (351 mg, 2.97 mmol). The resulting mixture was stirred at reflux for 18h. The reaction mixture was cooled to rt and extracted withEtOAc. The organic layer was washed three times with water, dried over Mg504, filtered and the solution was evaporated under reduced pressure. Thecrude product was purified by silica gel column chromatography using Hexanes/EtOAc (50:50) as eluent yielding 4-(5-bromo-2-methoxyphenyl)-1- thiomorpholine-1,1-dione Ex.49a (900 mg, 95%). 1H NMR (400 MHz, DMSOd6, d in ppm): 3.22 (t, 4H, J=5.2Hz), 3.41-3.46 (m, 4H), 3.80 (s, 3H), 6.92-6.96(m, 1H), 7.12 (d, 1H, J=2.4Hz), 7.18 (dd, 1H, J=8.6Hz, J=2.4Hz).

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, 5-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (144 pag.)WO2018/138359; (2018); A1;,
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Reference of 22236-10-8, 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 22236-10-8 as follows.

A solution of 4-difiuoromethoxyaniline (258 mg, 1.62 mmol) and 4-difluoromethoxyphenyl isocyanate (300 mg, 1.62 mmol) in toluene (8.1 niL) is heated at 7O0C for 1.5 h. The resulting white solid is collected by suction filtration and dried with suction for 30 min to obtain N,N’-bis[4- (difluoromethoxy)phenyl]urea as a white solid. 1H NMR: (CD3OD) 7.45 (dd, 4H), 7.09 (dd, 4H), 6.91(dt, 2H, Ji = 56 Hz).

According to the analysis of related databases, 22236-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/49941; (2006); A2;,
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Electric Literature of 7252-83-7, A common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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.

DMF (1mL) imidazole-2-carboxaldehyde in (0.41 g, 4.27mmol) to a solution containing 1.1 equivalents of 2-bromo-1,1-dimethoxyethyl(0.79 g, 4.69 mmol) It was added potassium iodide potassiumcarbonate and a catalytic amount. The reaction was heated 18 hours at 110 C.,then to dryness and evaporated, and purified using Biotage SP4 in gradientmethod 5-50% in DCM, produces the desired compound (248 mg, 1. 35mmol, 32%yield).

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; MOLECULAR INSIGHT PHARMACEUTICALS INCORPORATED; BABICH, JOHN W; (133 pag.)JP5856247; (2016); B2;,
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Electric Literature of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of methyl 2-cyanoacetate (0.885 ml, 10.09 mmol) in DMF (20.18 ml) at rt was added sodium hydride (0.969 g, 24.22 mmol), and the reaction mixture was stirred at rt for 15 min. tetrabutylammonium iodide (0.373 g, 1.009 mmol) and ((2-bromoethoxy)methyl)benzene (3.35 ml, 21.19 mmol) were added, and the reaction mixture was stirred at 90 ¡ãC for 3 h. Water was added and the aqueous layer was extracted with ether (x3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered, and the filltrate was evaporated in vacuo to give the crude product. The crude product was purified by silica gel chromatography eluting with 0-30percent ethyl acetate/hexanes to give methyl 4-(benzyloxy)-2-(2- (0187) (benzyloxy)ethyl)-2-cyanobutanoate (2.4 g, 6.53 mmol, 64.7 percent yield) as a colorless oil. NMR (500MHz, CHLOROFORM-d) delta 7.41 – 7.27 (m, 10H), 4.49 (s, 4H), 3.78 – 3.69 (m, 5H), 3.45 (s, 3H), 2.49 – 2.40 (m, 2H), 2.06 (dt, J=14.2, 4.7 Hz, 2H).

The synthetic route of ((2-Bromoethoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WU, Yong-Jin; GUERNON, Jason M.; (102 pag.)WO2018/81384; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 36865-41-5, name: 1-Bromo-3-methoxypropane

To a 1 L single-neck flask were added methyl 4-bromo-2-hydroxybenzoate (44.5 g, 193 mmol) and CH3CN (450 mL). After the solid was dissolved completely by stirring, K2C03 (39.9 g, 289 mmol) and 1-bromo-3-methoxypropane (45.1 g, 289 mmol) were added in turn. The resulting mixture was heated to 80 C and stirred for 12 hours at 80 C. After the reaction was completed, the reaction mixture was cooled to 25 C and filtered. The filter cake was washed with acetonitrile (100 mL). The combined filtrates was concentrated in vacuo, and the residue was diluted with EtOAc (500 mL). The mixture was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound as orange oil (58 g, 99.3%).MS (ESI, pos.ion) m/z: 303.2 [M¡ÂH] .

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; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; HUANG, Jianzhou; XIONG, Zhimin; XIONG, Jinfeng; LI, You; LIU, Yang; ZOU, Zhifu; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (2 pag.)WO2018/219356; (2018); A1;,
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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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, A new synthetic method of this compound is introduced below., Product Details of 38336-04-8

Benzethylethanolamine trimethylene carbonate: 2.7 g of benzyl alcoholamine modified 1,3-propanediol, 2.4 g of ethyl chloroformate and 30 ml of anhydrous tetrahydrofuran were placed in a 50 ml round bottom flask and stirred in an ice bath , 1.2 g of triethylamine dropwise, about 10 minutes drop finished. Remove the ice bath and react at room temperature for 2 hours. After filtration, the filtrate was concentrated and excess unreacted ether was added to precipitate white crystals and recrystallized three times with a mixed solvent of tetrahydrofuran and anhydrous ether in a volume ratio of 1: 3 to give white crystals in a yield of 64%. The infrared (FT-IR), nuclear magnetic resonance spectrum (1H NMR and 13C NMR) and elemental analysis (EA) data were the same as in Example 1

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; China University Of Geoscienceswuhan; ZHANG, Xiaojin; DAI, Yu; (6 pag.)CN106518836; (2017); A;,
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Application of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.

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

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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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. 1484-26-0, name is 3-Benzyloxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Benzyloxyaniline

Compound 19A (commercially available) (10.0 g, 50.25 mmol) was dissolved in water at room temperature and to resulting suspension K2CO3 ( 3.8 g, 27,64 mmol) was added. 3- Chloro propionylchloride (7.0 g. 55.28 mmol) was added dropwise for 30 minutes and stirred for 2 hours at room temperature The precipitate was filtered and washed with water. 1 N HCl, dried at 50 0C under vacuum overnight to provide 7.2 g of the product 19B.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/152200; (2009); A1;,
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