Ethers-buliding-blocks

Synthetic Route of 1116-77-4, 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. 1116-77-4, name is 4,4-Diethoxy-N,N-dimethyl-1-butanamine, This compound has unique chemical properties. The synthetic route is as follows.

Example 9 (0448) Synthesis of N-(4-(2-acetoxy-4-methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan- 1 -aminium bromide (0449) In a N2 purged 20mL weighed glass vial with stir bar is added 1 .5g (0.004mol, 1 .0 eq) of AcO-Bzp-OMe-CH2-Br prepared in Example 7 and 8 mL ethyl acetate to give a clear solution on stirring for 20mins at RT. 2.06 g 4,4-Diethoxy-N,N-dimethyl-1 -butanamine (0450) (NNDMABADEA, from TCI-America) (0.01 mol, 2.5 eq) is slowly added to the reaction solution with stirring. A precipitate is soon formed and gradually thickenes with stirring over 30- 60minutes. The reaction mixture is stirred at RT overnight. The stirring is stopped and the mixture is allowed to stand for an hour. The mixture is filtered through a coarse filter frit at around 850mbar. The precipitate is washed five times with 10ml_ ethyl acetate. The precipitate is transferred into a 10OmL rb flask with about 18ml of Dl Water. The residual organics are removed under reduced pressure to give a clear solution. The solution is filtered through a Whatman1 (1 1 urn) filter paper to give a clear solution with neutral pH, that is frozen and lyophilized to give a off white solid which is confirmed to be N-(4-(2-acetoxy-4- methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan-1 -aminium bromide and is stored under dry N2 in desiccator.

The chemical industry reduces the impact on the environment during synthesis 4,4-Diethoxy-N,N-dimethyl-1-butanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; CHANG, Frank; DESOUSA, Ryan; HOLLAND, Troy Vernon; LAREDO, Walter R.; (68 pag.)WO2017/93835; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

d) (4-Methyl-7-trifluoromethyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 4-Methyl-2-methylsulfanyl-7-trifluoromethyl-3,4-dihydro-quinazoline hydroiodide (116 mg, 0.30 mmol) and 2-phenoxyethyl amine (126 mg, 0.9 mmol) were dissolved in acetonitrile (0.9 ml) and heated to 170° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the reaction was diluted with little water and the precipitated product was filtered off, washed with water, dried in vacuo to yield the title compound as a white solid (104 mg, 94percent). (MS: m/e=350.2, 351.1 [M+H+]). 1H NMR (CDCl3): delta 1.25 (3H, d), 3.58 (2H, m), 4.05 (2H, t), 4.55 (1H, q), 6.08 (1H, bt), 6.37 (1H, s), 6.91-7.01 (5H, m), 7.11 (1H, d), 7.29 (2H, t).

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

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 62257-15-2, 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. 62257-15-2 name is 2-Fluoro-5-methoxyaniline, 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.

2-Fluoro-5-methoxyaniline (2.32 g, 16.4 mmol) was dissolved in acetic acid (11.6 mL) and water (1.16 mL), then a solution of potassium cyanate (1.33 g, 16.4 mmol) in water (1 mL) was added dropwise and the mixture was stirred at rt for 3 h. The reaction mixture was filtered, the filter cake was washed with water and ether and was dried under vacuum to give the title compound as an off-white solid. [M+H] = 185.1.

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

Reference:
Patent; DART NEUROSCIENCE, LLC; SANTORA, Vincent, John; CHEN, Mi; CHUNG, DeMichael; (377 pag.)WO2019/14305; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 52411-34-4,Some common heterocyclic compound, 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, molecular formula is C14H16N2O2, 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.

Compound 3 (2.44 g, 0.01 mol) was dissolved in MeCN(10 mL), then (i-Pr)2NEt (6 mL) and methyl bromoacetate (3 mL) were added to the mixture with stirring. The reaction mixture was refluxed for 24 h. After the reaction, the mixture was cooled down, poured into EtOAc (20mL), and filtered to remove the generated white solid. The combined EtOAc filtrates were concentrated in vacuo to give an oily solid, then adding a little methanol, white solid was generated, filtered, air dried and recrystallized in MeOH to give white solid 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(o-aminophenoxy)ethane, its application will become more common.

Reference:
Article; Cheng, Zhao; Yang, Bingqin; Yang, Meipan; Zhang, Binglin; Journal of the Brazilian Chemical Society; vol. 25; 1; (2014); p. 112 – 118;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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: 261762-35-0

A 100-mL round-bottom flask charged with Pd2dba3 (69 mg, 0.075 mmol), BINAP (112 mg, 0.18 mmol), and NaOt_Bu (650 mg, 6.5 mmol) was degassed and filled with N2. THF (20 mL) was added, followed by a solution 5-bromo-l,2-difluoro-3-methoxybenzene (1.1 g, 5 mmol) and l-(2,5-dimethoxyphenyl)ethanone (1.08 g, 6 mmol) in THF (10 mL). The resulting mixture was heated at 70 C for 16 h. Water (30 mL) was added, and the mixture was extracted with ether (3 x 50 mL). The combined organics were dried over anhydrous Na2S04, filtered, and concentrated to give the crude product, which was purified by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate = 80/1 ~ 40/1) to give 2-(3,4-difluoro-5- methoxyphenyl)-l-(2,5-dimethoxyphenyl)ethanone (0.4 g) as a light yellow solid. ¾ NMR (CDCI3): delta 7.24 (d, 1H), 7.04 (dd, 1H), 6.92 (d, 1H), 6.68-6.61 (m, 2H), 4.23 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.78 (s, 3H); LCMS: 323 (M+H)+.

The synthetic route of 5-Bromo-1,2-difluoro-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 62257-15-2, 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 62257-15-2 as follows.

Example 9: Intermediate 9~ 8-fluoro-5-methoxy-2-methylquinoline[0235] 8-Fluoro-5-methoxy-2-methylquinoline was synthesized from 2-fluoro-5-methoxyaniline (30.0 g, 213 mmol) according to the procedures described above for 8-chloro-5-methoxy-2- methylquinoline hydrochloride (Intermediate 1 , Step 1) with the following change: The hydrochloride salt was dissolved in dichloromethane (400 mL) and the pH of the resulting solution was adjusted to 8-9 with saturated aqueous potassium carbonate solution. The resulting mixture was extracted with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 20% ethyl acetate-petroleum ether) to afford 8-fluoro-5- methoxy-2-methylquinoline (25.2 g, 62%) as a yellow solid. MS (ESI, pos. ion) m/z 192[M+H]+. Step 1. 8-chloro-5-methoxy-2-methylquinoline hydrochloride [0204] A 1000-mL 3-necked round-bottom flask was charged with 2-chloro-5-methoxy aniline (50 g, 317 mmol), -butanol (120 mL), concentrated hydrochloric acid (37%, 90 mL), and chloranil (tetrachloro-l ,4-benzoquinone) (78 g, 317 mmol). The resulting solution stirred for 1 h at 100 C in an oil bath. A solution of (E)-crotonaldehyde (28.9 mL, 349 mmol) in -butanol (50 mL) was added dropwise over 1 h. The resulting solution stirred for 1 h at 100 C in an oil bath and was then cooled to 70 C. Tetrahydrofuran (650 mL) was added, and the reaction mixture stirred for 1 h at 70 C and was then cooled to 0 C. The resulting precipitate was held at 0- 5 C for 1 h. The mixture was filtered, the solids were washed with cold (ca. 0 C) THF (2 x 350 mL), and then dried in an oven to afford 8-chloro-5-methoxy-2-methylquinoline hydrochloride (83.0 g, 74%) as a yellow solid. MS (ES, m/z): 208 [M+H]+

According to the analysis of related databases, 62257-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 262587-05-3, These common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene, 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.

93 mg of 1 -bromo-3(dofluoromethoxy)benzene (0.42 mmol; 1.00 eq) and the successively 142 mg of 1 -[3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]azetidine-3-carboxylic acid (preparation 9; 0.42 mmol; 1.00 eq) dissolved in 4 mE of DME, 3.4 mg of Pd(dppf)C12, CH2C12 (0.01 eq.) and finally 127 mg of CsF (0.83 nnol; 2.00 eq) were introduced into a microwave- resistant 10 mE reaction vessel. The reaction mixture was microwave-irradiated for 1 h at 120 C. The reaction medium was then taken up with ethyl acetate and water, while adjusting the pH to 6, and then extracted with ethyl acetate and washed with brine. The organic phase was dried over magnesium suflate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (l3iotage 10 g silica 15-40 jtmlliquid deposit in dichloromethane) using a cyclohexane/0% to 100% dichloromethane gradient. The fractions containing the targeted product were combined and then evaporated, under reduced, pressure to give 99 mg of title compound in the form of a colorless oil,Yld: 33%.10548] ?H NMR (300 MHz, CHC13-d) oeppm 2.24 (s, 3H)3.41-3.49 (m, 1H) 3.62 (s, 3H) 3.92-4.02 (m, 4H) 6.18 (s, 1H) 6.32 (s, 1H) 6.43 (t, J=74 Hz, 1H) 6.68 (s, 1H) 6.93-6.96 (m, 1H) 7.19-7.3 1 (m, 3H).EC-MS mlz (M+H): 348.

The synthetic route of 262587-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 1758-46-9, The chemical industry reduces the impact on the environment during synthesis 1758-46-9, name is 2-Phenoxyethylamine, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of (0.137 g, 1 mmol)-2-phenoxy ethylamine-(1.0 mmol) triethylamine-and catalyst amount of DMAP was dissolved in 20 mL dichloromethane, then (R)-2-{4-[(3-chloro-5-trifluoromethylpyridin-2-yl)oxy]phenoxy}propanoic acyl chloride was added dropwise and stirred for 1 h at room temperature. When the reaction was complete, the mixture was washed with water and brine, dried over anhydrous sodium sulfate, and vacuumed to distillate solvent. Moreover, the crude product was purified with column chromatography silica gel using PE and EtOAc as eluent to give white solid 3a-m.p. 138~140C, yield 80.1% [alpha]20 D +20.33 (c 1, CH2Cl2); 1 H NMR (400 MHz, CDCl3) delta-7.85 (d, J = 2.2 Hz, 1H, pyridine), 7.50 (dd, J1 = 9.0, J2 = 2.2 Hz, 1H, pyridine), 7.29 (s, 1H, C6H5), 7.25 (s, 1H, C6H5), 7.04 (d, J = 9.0 Hz, 2H, C6H4), 6.94 (t, J = 9.0 Hz, 3H, C6H5), 6.84 (d, J = 8.7 Hz, 2H, C6H4), 4.67 (q, J = 6.8 Hz, 1H, CHCH3), 3.97~4.10 (m, 2H, COOCH2), 3.70 (m, 2H, OCH2), 1.58 (d, J = 6.8 Hz, 3H, CH3). EI-MS m/z 480.1 [M + ]. Analysis calculated for C21H21ClFN3O3S C 64.78, H 4.78, N 9.06; found C 64.76, H 4.70, N 9.03.

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-Phenoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hui, Yang Zi; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 385 – 387;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9, HPLC of Formula: C8H11NO

Example 55; 6- (2-Phenoxy-ethylamino)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine Hydrochloride; Use a method similar to the General Procedure 5-1, using 3- (2, 2,2-trifluoroacetyl)- 6-trifluoromethanesulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [dlazepine (100 mg, 0.23 mmol) and phenoxyethylamine (63 mg, 0.4 mmol) to give, after chromatography on silica gel eluting with hexane/EtOAc (85: 15) followed by SCX chromatography, 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-1H-benzo[d]azepine as a yellow oil. MS (ES+) m/z : 379 (M+H) +. Use a method similar to the General Procedure 1-1 to deprotect 6- (2-phenoxy- ethylamino)-3- (2, 2,2-trifluoroacetyl)-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (75 mg, 0.19 mmol). Purify by SCX chromatography to give the free base of the title compound. Use a method similar to the General Procedure 2-2 to give the title compound as a white solid. MS (ES+) m/z : 283 (M+H) +.; General Procedure 5-1; Dissolve the appropriately substituted 3- (2, 2, 2-trifluoroacetyl)-6-trifluoromethane- sulfonyloxy-2, 3,4, 5-tetrahydro-lH-benzo [d] azepine (1 equiv. ), palladium (II) acetate (0.1- 0.4 equiv. ), BINAP (0.2-0. 8 equiv. ; BINAP/catalyst ratio 2: 1) and cesium carbonate (1.4- 3. 0 equiv. ) in toluene (0.2-0. 05 M solution). Add the amine (1-3 equiv. ), degas the mixture with vacuum/nitrogen or argon purge and heat at 80-110°C for 4-16 h. Cool the mixture to ambient temperature, dilute with EtOAc, filter through a pad of silica gel or through Celitet) washing with EtOAc or ether, and evaporate the solvent to obtain the crude mixture. Alternatively, partition the reaction mixture between brine or saturated aqueous NaHCO3 and EtOAc, ether or DCM, dry the organic layer over Na2S04, and concentrate to obtain the crude mixture. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc mixtures and further SCX chromatography if needed.

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; ELI LILLY AND COMPANY; WO2005/82859; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 589-10-6, 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 589-10-6 as follows.

A solution of 0.24 g (10 mmol) of sodium hydride and15 ml of N, N-dimethylformamide was added50ml round bottom flask,Stirred at room temperature for 10 minutes, then 2.5 g (10 mmol) of compound 2 and 10 mmol were added2-phenoxyethyl bromide,And followed by thin layer chromatography to the end of the reaction, and then the reaction solution into 500ml ice water,Extracted three times with 100 ml of ethyl acetate, the organic phases were combined, the solvent was evaporated,The resulting residue was purified by silica gel column chromatography (V dichloromethane: V methanol = 100: 1) to give Compound 3 (2.3 g, yield 63%).

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Lu Xing; Huang Kunyuan; (13 pag.)CN106478676; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem