Ethers-buliding-blocks

Electric Literature of 20059-73-8, 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. 20059-73-8, name is 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1 1.5 kg of 4-(2-dimethylaminoethoxy)-benzylamine dissolved in sec-butanol and DMF obtained as described in the previous example are charged into a reactor and 12.7 kg of 37% hydrochloric acid are added dropwise. The pH is checked to ensure it is <1.0 and the precipitated mixture is stirred at 45-50C for at least 30 minutes. The mixture is cooled to 0-5C, centrifuged and the precipitate washed with 1 1.5 kg of sec-butanol. It is dried under vacuum at 70-80C. 13.5 kg of 4-(2- dimethylaminoethoxy)benzylamine dihydrochloride are obtained with HPLC purity higher than 98%. Reaction yield calculated on the 4-(2-dimethylaminoethoxy)- benzylamine 85.8%. 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, 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ERREGIERRE S.p.A.; WO2006/51079; (2006); A1;,
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Synthetic Route of 1116-77-4, 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 1116-77-4 as follows.

Example 3Reaction of 4-(1,2,4-triazol-1-yl-methyl)phenyl-hydrazine (IV) with 4-N,N-dimethylamino-butyraldehyde diethyl acetal (X) (Fischer indole synthesis)To the aqueous hydrazine (IV) solution obtained in example 2, conc. sulfuric acid (4.371) was added and the temperature of the reaction mixture was maintained for 2 hours at 65-70 C. After cooling to 20-25 C., 4-N,N-dimethylamino-butyraldehyde diethyl acetal (X) (3.15 kg) was added. The reaction was heated to 70 C. and maintained for 3-4 hours. After completion of the reaction, the reaction mixture was allowed to cool to 15-20 C. To this mixture, 25% aq. ammonia (7.251) was added to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4×12.251). A solution of succinic acid (2.45 kg) in water (301) was added to the ethyl acetate extract. The mixture was stirred for 15 minutes. The aqueous layer was separated and washed with ethyl acetate (2×51). The aqueous layer was basified with 20% aq. NaOH to adjust the pH to 8.5-9. The solution was extracted with ethyl acetate (4 x 51). The combined ethyl acetate extracts were concentrated to give rizatriptan free base (VII) as oil (2.8 kg, 75.5% from 4-(1,2,4-triazol-1-yl-methyl)phenylamine (II)). Purity =99.7-99.9% (as measured by HPLC).

According to the analysis of related databases, 1116-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gore, Vinayak G.; Kulkarni, Vikas S.; Wavhal, Sneha R.; US2010/256208; (2010); A1;,
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Some common heterocyclic compound, 105404-89-5, name is 2,7-Dibromo-3,6-dimethoxynaphthalene, molecular formula is C12H10Br2O2, 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. Application In Synthesis of 2,7-Dibromo-3,6-dimethoxynaphthalene

0.125 mol [intermediate 1-1] at room temperature,43.4 g and (4-chloro-2-fluorophenyl) boronic acid 0.301 mol, 52.5 g and Ce2CO3 0.815 mol, 266 g and TTP (tetrakis(triphenylphosphine)palladium(0)) 8 mol% 11.6 g was added with 500 mL of 1,4-dioxane and refluxed. After 4 hours, the reaction was cooled to room temperature, 500 ml of H2O was added, and extracted with EA.After filtration, the obtained solid was recrystallized from EA (ethyl acetate) and Hx (normal hexane) to obtain 0.09 mol of [Intermediate 1-2] and 41.0 g (yield 73%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105404-89-5, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Kim Myeong-gon; Keum Su-jeong; Yoon Jeong-min; (52 pag.)KR2019/111688; (2019); A;,
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Related Products of 38336-04-8, 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 38336-04-8 as follows.

To a stirred mixture of 7-bromo-4-chloro-3-nitroquinoline (20 g, 69.57 mmol, 1 equiv) and 2-(benzyloxy)ethan-l-amine(12.0 g, 79.30 mmol, 1.14 equiv) in DCM(400 mL) was added TEA(10.6 g, 104.35 mmol, 1.50 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 16 h at room temperature under nitrogen atmosphere. The resulting mixture was concentrated under vacuum. This resulted in N-[2-(benzyloxy)ethyl]-7-bromo-3-nitroquinolin-4- amine(30 g) as a yellow crude solid. LC-MS: (ES, m/z): [M+H]+ = 402.2/404.2.

According to the analysis of related databases, 38336-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; OLHAVA, Edward James; O’MALLEY, Daniel; (222 pag.)WO2018/152396; (2018); 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. Application In Synthesis of 3-Fluoro-4-methoxyaniline

To a mixture of cyanuric chloride (0.368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) inCH3CN followed by the additionof N, N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, 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 sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluting with 96: 3: 1 methylene chloride: methanol: cone. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp68-69 OC ; HPLC: Inertsil ODS-3V C18, 40: 30: 30[KH2P04(0. 01 M, pH3. 2) :CH30H : CH3CN], 264nm, Rt 8.2 min, 97.1percent purity ; MS (ESI):lnlz 458 (M+H, 100), 362 (2.8), 230(85. 4).

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; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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Reference of 1836-62-0, These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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: Compound 2a (100 mg, 0.52 mmol), and 2-(2-methoxyphenoxy)ethanamine (150 mg, 0.62 mmol) were added to ethanol and theresulting heterogeneous solution was reuxed for 24 h. Themixture was cooled to room temperature and ltered through a padof celite and the ltrate was concentrated under reduced pressure.The residue was puried by ash chromatography on silica-gelwith 10% methanol in ethyl acetate. Yielding 68% compound 6a(128 mg) as a white solid. Compound 6b was synthesized followingthe procedure of preparation 6a.

Statistics shows that 2-(2-Methoxyphenoxy)ethylamine is playing an increasingly important role. we look forward to future research findings about 1836-62-0.

Reference:
Article; Xu, Yao; Chen, Shujun; Cao, Ying; Zhou, Pingzheng; Chen, Zhipeng; Cheng, Kui; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 253 – 266;,
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Electric Literature of 39021-83-5, 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. 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1,4-dimethoxy-2,3-dimethylbenzene 1 (1.50 g, 9.0 mmol), N-bromosuccinimide (6.43 g, 36.1 mmol) and benzoyl peroxide (0.22 g, 0.9 mmol) in benzotrifluoride (220 cm3) was heated under reflux for 2.5 h and then allowed to cool and filtered. The filtrate was evaporated to give an orange residue, shown by 1H NMR and TLC to contain a mixture of the desired product 2 and the ring brominated product 8. Recrystallisation (petroleum ether/ethyl acetate, 3:1) gave the desired product 2 (1.03 g, 35%) as a pale yellow solid, mp and 1H NMR data as above.

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, 1,4-Dimethoxy-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aitken, R. Alan; Jethwa, Siddharth J.; Richardson, Neville V.; Slawin, Alexandra M.Z.; Tetrahedron Letters; vol. 57; 14; (2016); p. 1563 – 1566;,
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Application of 450-88-4,Some common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Description 18; : 3-Bromo-6-fluoro-2-(methyloxy)benzaldehyde (D18)To a solution of diisopropylamine (6.89 g, 9.6 ml_, 68.3 mmol) in THF (100 ml.) at -78 C was added n-butyl lithium (33.5 ml. of 1.6 M solution in hexane, 53.6 mmol) over 3 mins. After stirring at -78 C for 10 mins, 2-bromo-5-fluroanisole (10 g, 48.8 mmol) in THF (20 ml.) was added dropwise over 15 mins. After completion of the addition, the mixture was stirred at -78 C for 1 hr and then DMF (3.91 g, 4.12 ml_, 53.6 mmol) was added dropwise over 3 mins and stirring was continued at -78 C for 45 mins. Saturated NH4CI solution was added and the mixture allowed to each room temperature. Diethyl ether and 2M HCI were added, the product was extracted into diethyl ether and the combined extracts were washed with brine, dried and evaporated. Chromatography on silica gel followed by trituration of the product with diethyl ether gave the title compound (D18) as a yellow solid (6.84 g) NMR (deltaH), (CDCI3): 3.97 (3H, s), 6.90 (1 H, m), 7.76 (1 H, dd, J = 5.9, 11.0 Hz), 10.34 (1 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
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Application of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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.

To a solution of 4-bromo-3-methoxyaniline (1k) (2.00 g, 9.9 mmol) in water (50 mL) was added hydrochloric acid (4 mL) and sodium nitrite , NaNO2) (0.75 g, 10.9 mmol) is slowly added at 0°C. The mixture was stirred at 0 °C for 30 minutes and then potassium carbonate (1.67 g, 11.9 mmol), copper cyanide (CuCN) (1.06 g, 11.9 mmol) and potassium cyanide (KCN) Mmol) dissolved in water (50 mL). The mixture is stirred at 70°C , cooled, and extracted with toluene. Magnesium sulfate is added to the extracted organic layer to remove water and concentrated under reduced pressure. The concentrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ether = 6: 1) , 4-bromo-3-methoxybenzonitrile can be obtained in the form of yellow powder.

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; Konkuk University Industrial Cooperation Corp; Chong, Yu-Hun; Park, Kwang-Su; Kim, Mi-Kyung; Kim, Kyung-Do; (20 pag.)KR2017/17173; (2017); A;,
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Reference of 6781-17-5, A common heterocyclic compound, 6781-17-5, name is 2-(2-Ethoxyphenoxy)ethanamine, molecular formula is C10H15NO2, 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.

4.87 g of 2-methoxy-5-(2-oxopropyl)benzenesulfonamide, 3.62 g of 2-(2-ethoxyphenoxy)ethylamine and 10 mg of sodium acetate were added to 30 ml of acetonitrile. The mixture was heated while stirred under reflux for about 1 hour. Then, the solvent was evaporated off in vacuo, to give 7.84 g of an imine compound as a powder. The obtained imine compound was again dissolved in 70 ml of acetonitrile, and to this was added 1.0 g of anhydrous magnesium sulfate. The mixture was cooled to -3 to 3C under argon atmosphere. To this mixture was added the whole amount of the above catalyst-containing mixture, and stirring continued at the same temperature for about 30 minutes. To this was added dropwise 12.0 ml of a mixed solution of formic acid/triethylamine (molar ratio: 5/2), and then stirring further continued at the same temperature for about 5 hours. After that, the reaction mixture was gradually returned to room temperature, and stirring continued overnight for completion of the reaction. After that, the solvent was evaporated off in vacuo and the residue was dissolved in methyl isobutyl ketone. Following this, extraction with aqueous methanesulfonic acid solution was performed. After the aqueous layer was rendered weakly alkaline with aqueous sodium hydroxide solution, separated oily material was extracted with methyl ethyl ketone. The extract solution was washed with saturated brine, dried and concentrated, to give 7.96 g of 5-[2-[(2-(2-ethoxyphenoxy)ethyl)amino]propyl]-2-methoxybenzenesulfonamide (crude crystal containing excess R-isomer) as a light brown powder. The obtained compound was analyzed using a chiral chromatography column (CHIRALPAK AD-H; manufactured by Daicel Chemical Industries, Ltd.) with a solvent made of n-hexane/2-propanol/diethylamine (800/200/1). The result showed that the optical purity of the R-isomer was 70.7%ee. Then, 6.0 g of the crude crystal was dissolved in 42.0 ml of aqueous acetone containing 10% water and to this was added 3.36 g of (R)-mandelic acid. The mixture was heat-dissolved, and then allowed to stand at 15 to 25C overnight. The precipitate was collected by filtration, washed with acetone and dried, to give 4.56 g of (R)-tamuslosin (R)-mandelate, i.e., (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide (R)-mandelate as a colorless crystal. The optical purity of the R-isomer of the obtained compound was 97.0%ee. Moreover, recrystallization from aqueous acetone containing 10% water was performed to give 3.29 g of a purified product. The optical purity of the R-isomer of the purified product was 100%ee.Optical rotation: [alpha]D20 -31.90 (C = 0.5, MeOH) NMR: 1H-NMR (200MHz, DMSO-d6): delta 0.99-1.03 (3H, d), 1.23-1.30 (3H, t), 2.47-2.59 (1H, q), 2.97-3.05 (1H, q), 3.10-3.30 (1H, m), 3.14-3.20 (2H, t), 3.88 (3H, s), 3.94-4.04 (2H, q), 4.09-4.15 (2H, t), 4.43 (2H, m), 4.75 (1H, s), 6.82-7.43 (9H, m), 7.04 (2H, m), 7.58-7.60 (1H, d)

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; Hamari Chemicals, Ltd.; EP2172443; (2010); A1;,
Ether – Wikipedia,
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