Ethers-buliding-blocks

Application of 645-36-3, These common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, 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.

2,2-Diethoxyethylamine (430 muL, 2.95 mmol) and Na2CO3 (0.285g, 2.69 mmol) were added to a stirred soln of pyrimidine 717 (0.645g, 2.69 mmol) in i-PrOH (20 mL). After 5 min, H2O (50 mL) was added and the product was extracted with CH2Cl2 (2 × 50 mL). The organic layers were combined, washed with H2O (2 × 20 mL), dried(Na2SO4), and concentrated. The residue was purified by flash chromatography[silica gel, hexane-benzene (1:1); Rf = 0.15] to give a yellow solid; yield: 0.40 g (44%); mp 71.5-73.5 C.IR (KBr): 3364 (NH) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.28 (t, J = 7.2 Hz, 6 H, 2 × CH3),2.58 (s, 3 H, SCH3), 3.61 (dq, 2J = 9.3 Hz, 3J = 7.2 Hz, 2 H,2 × CHAHBCH3), 3.73-3.85 (m, 4 H, NCH2 and 2 × CHAHBCH3),4.69 (t, J = 5.4 Hz, 1 H, OCH), 8.17 (br s, 1 H, NH).13C NMR (75 MHz, DMSO-d6): delta = 14.5, 15.7, 44.3, 62.3, 99.8,124.6, 152.6, 154.6, 173.0.Anal. Calcd for C11H17ClN4O4S: C, 39.23; H, 5.09. Found: C,39.21; H, 5.07.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 1758-46-9 as follows. Quality Control of 2-Phenoxyethylamine

d) (6-Chloro-4-methyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 6-Chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (106 mg, 0.30 mmol) and 2-phenoxyethyl amine (168 mg, 1.2 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 layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, the solvent was evaporated and the residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1) to yield the title compound as a white solid (88 mg, 93percent). (MS: m/e=316.0, 318.0 [M+H+]). 1H NMR (CDCl3): delta 1.23 (3H, d), 3.56 (2H, m), 4.05 (2H, t), 4.47 (1H, q), 5.95 (1H, bs), 6.27 (1H, bs), 6.69 (1H, d), 6.90-7.01 (4H, m), 7.29 (2H, t).

According to the analysis of related databases, 1758-46-9, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 1036724-54-5, 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 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in 15 THF (100 mL) was added 11 potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M 16 HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 17 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow 18 oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5467-58-3, A common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

Under nitrogen conditions,To the magnetic stirrer,thermometer,6.6 g (27.9 mmol) was added to a 250 mL three-necked flask of a condenser.1-bromo-4-methoxynaphthalene,12.0 g (36.3 mmol) of 4-nitrophenyl-2-amino-9,9-dimethylhydrazine,10.6g (167.4mmol) of copper powder,23.1 g (167.4 mmol) of potassium carbonate,7.4 g (27.9 mmol) of 18-crown-6,Then add 57.2 ml of o-dichlorobenzene,Reacting at 170 C for 20 h;The mixture was filtered while hot, and o-dichlorobenzene was distilled off under reduced pressure. The crude product was recrystallized from ethanol and N,N-dimethylacetamide (V:V = 1:2.7) to give 4-nitrophenyl-4. ‘-Methoxynaphthyl-2-amino-9,9-dimethylhydrazine 10.2 g, yield 75%;

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Chen Chunhai; Su Kaixin; Wang Daming; Sun Ningwei; Zhou Hongwei; Zhao Xiaogang; (24 pag.)CN108929297; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H9BrO

Same procedure as in lit.32 with modifications: a biphasic solution of 2-bromo-1-phenoxy ethane32b (20.0 g, 0.1 mol), NBu4HSO4 (33 g, 0.1 mol) in Et2O (400 mL) and 50% aqueous NaOH (100 mL) was vigorously stirred at rt for 4 h. The organic phase was washed with H2O (3 × 50 mL), the aqueous phases were extracted with Et2O (2 × 50 mL), the combined organic phases dried (MgSO4) and evaporated. 27b was purified by distillation (7.8 g, 65%) at 70 C, 28 Torr. The reaction in toluene as in lit.32b gave a weaker yield (40%).1H NMR (250 MHz, CDCl3): similar values as in lit.37 S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis (2004), pp. 2833-2836. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (21)37

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:
Article; Chevrier, Carine; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Carbohydrate Research; vol. 346; 10; (2011); p. 1202 – 1211;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Recommanded Product: 74137-36-3

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole percent, 20.66 mg), triphenylphosphine (4 mole percent, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32percent (751 mg). C10H9Br3O; MW 256/258; 1H-NMR (CD3OD): delta 7.61 (d, J=16.1 Hz, 1H), 7.38-7.37 (m, 1H), 7.17-7.16 (m, 2H), 6.53 (d, J=16.1 Hz, 1H), 3.87 (s, 3H); 13C-NMR (CD3OD): delta 169.8, 162.3, 144.5, 138.9, 124.2, 121.4, 120.0, 113.4, 56.2

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, 1,3-Dibromo-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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 116557-46-1, SDS of cas: 116557-46-1

A suspension of 3-bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg, 2.97 mmol) and potassium acetate (729 mg, 7.42 mmol) in 1,4-dioxane (8 mL) was sparged with nitrogen for 5 min. Pd(dppf)Cl2·DCM (173 mg, 0.21 mmol) was added and the mixture was heated under reflux for 2.5 h then cooled to room temperature. The reaction was diluted with DCM (35 mL) and washed with water (35 mL). The organic phase was concentrated under reduced pressure then purified by flash column chromatography, eluting with 0-100% EtOAc in isohexane, to return 49h (358 mg, 58%) an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 6.72-6.83 (m, 3H), 4.80 (s, 2H), 3.64 (s, 3H), 1.28 (s, 12H).

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; Newton, Rebecca; Bowler, Katherine A.; Burns, Emily M.; Chapman, Philip J.; Fairweather, Emma E.; Fritzl, Samantha J.R.; Goldberg, Kristin M.; Hamilton, Niall M.; Holt, Sarah V.; Hopkins, Gemma V.; Jones, Stuart D.; Jordan, Allan M.; Lyons, Amanda J.; Nikki March; McDonald, Neil Q.; Maguire, Laura A.; Mould, Daniel P.; Purkiss, Andrew G.; Small, Helen F.; Stowell, Alexandra I.J.; Thomson, Graeme J.; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 20 – 32;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 5414-19-7 as follows. Safety of 1-Bromo-2-(2-bromoethoxy)ethane

Part F:; To a DMF (9 mL) solution of Part E (1.08 g, 2.71 mmol) was added K2CO3 (1.12 g, 8.16 mmol), 18-crown-6 (0.21 g, 0.80 mmol), and bis (2-bromoethyl) ether (0.37 mL, 2.9 mmol). The slurry was stirred at 60C for 72 hr. Additional bis (2-bromoethyl) ether was added at 24 hr (0.4 mmol) and 48 hr (1.2 mmol). The solvent was stripped in vacuo, and the residue was partitioned between ethyl acetate (50 mL) and water (30 mL). The organic layer was separated, dried over MgS04, and evaporated to an oil. Recrystallization from diethyl ether produced 0. 88 g (69 %) of the desired compound in the form of a white solid. LCMS: itvz = 469.2 (M+H).

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2005/42521; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 60792-79-2, 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. 60792-79-2 name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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.

N,N-(2,2′-oxybis(ethane-2.1-divfflbis(2,4,6-trimethylaniline) (Example 1 1) [0088] In a drybox, 2,4,6-trimethylbromobenzene (500.0 muL, 3.27 mmol), 2,2′- oxydiethylamine dihydrochloride (289.3 mg, 1.63 mmol), sodium terf-butoxide (706.5 mg, 7.35 mmol), 4.0 mL of dimethyoxyethane, and 10.0 mM Pd(OAc)2 / CyPF-r-Bu (81.8 muL, 8.18 x 10-4 mmol) were added to a 20 mL scintillation vial equipped with a magnetic stirbar and sealed with a cap containing a PTFE septum. The reaction was placed into a temperature controlled aluminum heating block and stirred at 100 0C for 6 h. After cooling to room temperature, the reaction mixture was partitioned between 100 mL H2O/Et2O (1 :1), the organic phase separated and dried over MgSO4, followed by the removal of all volatiles to afford 505 mg (91.0 %) of the title compound.[0089] 1H NuMR spectra were obtained at 400 MHz and recorded relative to residual protio solvent. 13C NuMR spectra were obtained at 101 MHz and recorded relative to the residual solvent resonance. The spectra recorded are as follows:Eta NuMR (CDC13, 400 MHz, 22 0C): delta 2.24 (s, 6H), 2.28 (s, 12H), 3.15 (t, J= 5.0 Hz, 4H), 3.49 (br s), 3.61 (t, J = 5.0 Hz, 4H), 6.84 (s, 4H). 13C NuMR (CDCI3, 101 MHz, 22 0C): delta 18.2, 20.5, 48.2, 70.4, 129.4, 129.8, 131.3, 143.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2′-Oxybis(ethylamine) dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVATION TECHNOLOGIES, LLC; JOHNS, Adam, M.; WO2010/53696; (2010); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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. Formula: C7H7FO

The crude product (1.0 g, 7.9 mmol) was dissolved in acetonitrile (15 mL) and N-bromosuccinimide (1.4 g, 8.7 mmol) was added and reacted at 70 C for 3 h. After the reaction was completed, most of the acetonitrile was distilled off, 30 mL of water was added, the mixture was stirred for 10 min and extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over anhydrous magnesium sulfate and separated by column chromatography (pure petroleum ether as eluent) The brominated product (intermediate A_2c) was obtained as a light yellow oily liquid (1.4 g, yield 86%) oA-2c: SH (300 MHz; CDCl 3) 7.23-7.16 (2H, m), 6.82 (D, J = 8.7Hz), 3.86 (3H, s); delta (75MuEtazeta; CDC13) 152.3 (d, Jc, F = 249.0Hz), 147.1 (d, 119.6 (d, J = 21.1 Hz), 114.6 (d, J = 2.2 Hz), 111.9 (d, J = 8.2 Hz), 56.4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 321-28-8, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Chemical Institute; Yu Chuyi; Li Yixian; Jia Tengdun; Zhao Xuan; (27 pag.)CN104557654; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem