Category: ethers-buliding-blocks

Application of 13101-88-7,Some common heterocyclic compound, 13101-88-7, name is 6-Methoxynaphthalen-2-amine, molecular formula is C11H11NO, 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.

28.2 g (0.16 mol) of the product synthesised in the previous step are dissolved in a mixture of dichloromethane/methanol: 1500/620 ml. To the resulting solution add, at ambient temperature, 56.7 g (0.16 mol) of benzyltrimethylammonium dichloroiodate and 21.2 g (0.212 mol) of calcium carbonate. After 30 minutes, filter off the insoluble material, then take up the organic phase with 10% sodium bisulphite solution and extract with ethyl ether. Dry over magnesium sulphate, filter and then evaporate. The residue is purified by chromatography over silica gel using a mixture of cyclohexane/ethyl acetate:70/30:v/v as eluant.

The synthetic route of 13101-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lavielle, Gilbert; Muller, Olivier; Millan, Mark; Gobert, Alain; Di Cara, Benjamin; US2005/59675; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 6443-69-2, 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. 6443-69-2 name is 1,2,3-Trimethoxy-5-methylbenzene, 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.

Reference Example 3 To a solution of 18-acetoxy-n-octadecanoyl chloride (11 g) in 1,2-dichloroethane (50 ml) is added aluminum chloride (7 g) and the mixture is stirred at room temperature for 2 hours. This reaction mixture is cooled to 5 C. and a solution of 3,4,5-trimethoxytoluene (6.2 g) in 1,2-dichloroethane (20 ml) is added. The mixture is stirred at room temperature for 72 hours. Then, this reaction mixture is heated to 50 C.-60 C. and stirred for 30 minutes. After cooling, ice-water is added to the reaction mixture and the product is extracted with dichloromethane. The dichloromethane layer is washed with water and the solvent is distilled off to recover an oil (12.1 g). This oil is dissolved in methanol (150 ml) followed by addition of sodium hydroxide (5.2 g). The mixture is stirred at room temperature for 2 hours, at the end of which time it is neutralized with 5N–HCl and the solvent is distilled off. The resultant crude crystals are rinsed with water and recrystallized from dichloromethane-ether (1:1). The above procedure yields 6-(18-hydroxy-1-oxooctadecyl)-2,3-dimethoxy-5-methylphenol (6.4 g) as colorless needles, m.p. 101 C. Elemental analysis for C27 H46 O5. Calcd. C, 71.96; H, 10.29. Found C, 72.08; H, 10.51.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2,3-Trimethoxy-5-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4495104; (1985); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 54314-84-0,Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

To a stirred suspension of 4-chloro-3-hydroxy-5-nitrobenzamide (30 g, 139 mmol) and potassium carbonate (57.4 g, 416 mmol) in DMF (200 mL) under nitrogen was added at room temperature a solution of ((3-bromopropoxy)methyl)benzene (47.6 g, 208 mmol) dropwise during 1 minute. The reaction mixture was stirred at 80 °C overnight. The reaction mixture was cooled to room temperature and quenched by the addition of 200 mL of water. The aqueous phase was then extracted with DCM (3×100 mL). The combined organic layer was washed with water (4×200 mL) and brine (200 mL), dried, and concentrated under vacuum. The crude product was purified by silica gel chromatography (100 g column, 1:2 petroleum ether/EtOAc). The appropriate fractions were pooled and concentrated to afford 3-(3-(benzyloxy)propoxy)-4-chloro-5-nitrobenzamide (33 g, 90 mmol, 65.3percent yield) as a yellow solid. LCMS (m/z): 365 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route ((3-Bromopropoxy)methyl)benzene, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FOSBENNER, David T.; GRAYBILL, Todd L.; KANG, Jianxing; KING, Bryan W.; LAN, Yunfeng; LEISTER, Lara Kathryn; MAHAJAN, Mukesh K.; MEHLMANN, John F.; MORALES-RAMOS, Angel I.; PESIRIDIS, George Scott; RAMANJULU, Joshi M.; ROMANO, Joseph J.; ROMERIL, Stuart Paul; SCHULZ, Mark J.; ZHOU, Huiqiang; (372 pag.)WO2019/69270; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: To a solution of compound 1 (1.18 g, 4 mmol) in THF 30 mL was added TEA (1.1 mL, 8 mmol) and series amine (8 mmol) dropwise with stirring. The reaction mixture was refluxed for 6 h. The mixture was concentrated and extracted with ethyl acetate, dried over MgSO4, and the solvent was removed in vacuo. The formed precipitate was filtered off and dried in vacuo. Recrystallization from hexane and ethyl acetate, washed with acetone.

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Chun-Liang; Chang, Deh-Ming; Chen, Tsung-Chih; Lee, Chia-Chung; Hsieh, Hsi-Hsien; Huang, Fong-Chun; Huang, Kuo-Feng; Guh, Jih-Hwa; Lin, Jing-Jer; Huang, Hsu-Shan; European Journal of Medicinal Chemistry; vol. 60; (2013); p. 29 – 41;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 22094-18-4, 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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

Under a nitrogen atmosphere, a 5L three-neck flask was charged with a starting material, ethanesulfonamide (163.5 g, 1.5 mol).Anhydrous potassium carbonate (275.8g, 2.0mol) and anhydrous DMF (1L) were stirred for 30min.Then 1,3-dibromo-2,2-dimethoxypropane (SM) (259.9 g, 1.0 mol) was added,Stir for 30 min, then raise the temperature of the reaction system to 95-100 C.20-22 hours at this temperature,Then cool to room temperature.After that, the pH was adjusted to 2 to 3 with 0.1N HCl, and the mixture was stirred well for 2-3 hours. Then, 2L of water was added to the system to precipitate a lot of off-white solid, which was filtered and dried to obtain 134.1 g of a solid. The yield was 82.3. %.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2,2-dimethoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Xiamen Hailejing Biochemical Co., Ltd.; Zhong Baoxiang; Qiu Binglin; Chen Huadong; Li Jinlin; Huang Zhizheng; (9 pag.)CN107739328; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 18800-30-1, The chemical industry reduces the impact on the environment during synthesis 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, I believe this compound will play a more active role in future production and life.

General procedure: 6-Hydroxyphthalide (9) (0.33 mmol) was dissolved in N,N-dimethylformamide (DMF; 3 mL) and stirred over K2CO3 (1.14 mmol) for 5 min. The appropriately substituted alkyl bromide (0.37 mmol) was added and the reaction mixture was stirred for 12 h at 50-100 ºC. The K2CO3 was removed by filtration and the reaction mixture was dried in a stream of air. The resulting residue was recrystallized from ethanol to yield the C6-substituted phthalide analogues 6a-r.1 Benzylaminophthalide (6s) was synthesized according to the same procedure from 6-aminophthalide (8) and benzyl bromide

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, 1-Bromo-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Strydom, Belinda; Bergh, Jacobus J.; Petzer, Jacobus P.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1269 – 1273;,
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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, A new synthetic method of this compound is introduced below., name: 1-Bromo-2-(2-bromoethoxy)ethane

A solution of the ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate (500 mg, 2.95 mmol), Cs2CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA (10mL) as stirred at 120 oC overnight. Then H2O (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+H]+.

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; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; LIN, Kai; RHODIN, Michael, H.J.; McALLISTER, Nicole, V.; OR, Yat, Sun; (447 pag.)WO2019/67864; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 91-16-7, name is 1,2-Dimethoxybenzene, 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 91-16-7, Recommanded Product: 91-16-7

General procedure: A mixture of aldehyde 2 (1.0 mmol), aromatic compound 1(2.0 mmol) and BAILs (0.2 mmol) was stirred at 40?C for the desired time. The reaction was monitored by thin layer chromatography(TLC). After the completion of the reaction, 1 ml of water was added into the reaction mixture, and the target compound was obtained though simple filtration. The pure ionic liquids got by drying the filtrate were reused for another cycle. Synthesis route is listed in Scheme 2.

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; Wang, Ailing; Zheng, Xueliang; Zhao, Zhuangzhi; Li, Changping; Cui, Yingna; Zheng, Xuefang; Yin, Jingmei; Yang, Guang; Applied Catalysis A: General; vol. 482; (2014); p. 198 – 204;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, 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. Recommanded Product: 22483-09-6

To a 500 ml_ round-bottomed flask equipped with temperature probe and nitrogen inlet were added aminoacetaldehyde dimethyl acetal (25 g, 238 mmol) in aq. NaOH (4.85 M, 69 ml_) and toluene (125 ml_). The mixture was cooled to 0 C in an ice bath and benzylchloroformate (40.6 g, 238 mmol) was added at such a rate that the internal temperature was maintained below 20C. The reaction mixture was stirred for 4 h at room temperature. The layers were separated, and the organic layer was washed with brine (2 x 20 ml_), dried with sodium sulfate, filtered, and concentrated to a colorless oil (53.24 g, 93% yield). 1H-NMR (CDCI3, 500 MHz): 7.30 (m, 5H), 5.1 1 (s, 2H), 4.37 (t, J=6.0 Hz, 1 H), 3.39 (s, 6H), 3.33 (t, J=6.0 Hz, 2H). MS (electrospray): exact mass calculated for Ci2Hi7NO4, 239.12; m/z found, 240 [M+H]+.

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
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. 17061-62-0, name is Bis(4-methoxybenzyl)amine, A new synthetic method of this compound is introduced below., Quality Control of Bis(4-methoxybenzyl)amine

4-(3-Formyl-2-methoxy-phenoxymethyl)-N N-bis-(4-methoxy-benzyl)-benzenesulfonamide A solution of 4-(bromomethyl)benzenesulfonyl chloride (5.6 mmol) in 5 mL of CH2Cl2 at 25 C. is treated with Et3 N (8.4 mmol) followed by bis-(4-methoxy-benzyl)-amine (5.8 mmol). The reaction is stirred for 12 hours, diluted with H2O, extracted with CH2Cl2, dried (MgSO4), filtered and concentrated. The resultant crude material is purified by silica flash chromatography (20% EtOAc/hexanes) to yield 4-bromomethyl-N,N-bis-(4-methoxy-benzyl)-benzenesulfonamide: 1H NMR (400 MHz, CDCl3): delta 7.72 (apparent t, J=8.4 Hz, 2H), 7.44 (dd, J1=1.6 Hz, J2=8.4 Hz, 2H), 6.91-6.86 (m, 4H), 6.69 (d, J=8.8 Hz, 4H), 4.5 (s, 2H), 4.19 (s, 4H), 3.71 (s, 3H); LC/MS: (ES+) 490.1 (M+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; IRM LLC; US2009/325981; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem