Category: ethers-buliding-blocks

Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Computed Properties of C7H6F3NO

[00310] A reaction vial was charged with 2-benzyl-5-chloro-l,2,3,4-tetrahydro-2,6-naphthyridine(25.00 mg, 0.09662 mmol), 3-(trifluoromethoxy)aniline (42.8 mg, 0.000242 mol), tris(dibenzylideneacetone)dipalladium(0) (2.2 mg, 0.0000024 mol), xantphos (3 mg, 0.000005 mol), sodium tert-butoxide (14 mg, 0.00014 mol), and toluene (0.500 mL, 0.00469 mol) and tert-butyl alcohol (0.1 mL, 0.001 mol) and the vial was flushed with argon. The reaction mixture was then stirred at 110 0C in a microwave for 30 minutes. The reaction mixture was then filtered and solvent removed and the residue purified by prep HPLC to get the pure compound as a yellow solid. MS (M+H)= 400.4;1H-NMR (CDCl3): (400 MHz) 88.03 (d, 7=4.66 Hz, IH), 7.61 (bs, lH),7.48-7.44 (m, 2H), 7.40-7.28 (m, 5H), 6.83 (d, J=7.98 Hz, IH), 6.51 (d, 7=5.1 1 Hz, IH), 6.25 (bs, IH), 3.85 (s, 2H), 3.70 (s, 2H), 3.00 (t, J=5.50 Hz, 2H), 2.76 (t, 7=5.50 Hz, 2H)

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

Reference:
Patent; RENOVIS, INC.; WO2009/11904; (2009); A1;,
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 3401-47-6 as follows. Product Details of 3401-47-6

A mixture of 1-bromo-2-methoxynaphthalene (1.0 equiv.), Phenylboronic acid (1.5 equiv.) And K3PO4(3 equiv.), Toluene (2 mL / mmol of aryl bromide) and a catalyst (Pd content of 0.001 mol%) were added to a dry reaction tube with a magnetic stir bar.The reaction tube was then stirred at 100 C for 24 h under an argon atmosphere.After the reaction, the solution was cooled to room temperature, 5 mL of water was added and the mixture was extracted with 3 x 5 mL of ethyl acetate. The organic phases were combined and the organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated by rotary evaporation. chromatography to give the desired product(yield 28%).

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOOCHOW UNIVERSITY; LANG, JIANPING; NING, JINJIAO; REN, ZHIGANG; (13 pag.)CN104710255; (2016); B;,
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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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(2-Methoxyethoxy)aniline

To a solution of 2.4-dichloro-l,3,5-triazine A.91 (2 g, 13.34 mmol) in DMF (10 mL) at 0 0C were added DIEA (2.4 mL, 13.77 mmol) and 4-(2-methoxyethoxy)benzenamine (2.027 g, 12.12 mmol) and the mixture was stirred at 0 0C for 30 minutes and then room temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (50 mL x 1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The brown solid was purified by silica gel column chromatography using 30% of ethyl acetate in hexane as eluent to give 4-chloro-N-(4-(2-methoxyethoxy)phenyl)-l,3,5-triazin-2-amine A.92 (2.887 g, 84.8% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 10.58 (1 H, s), 8.56 (1 H, d, J=5.9 Hz), 7.51 (2 H, t, J=9.5 Hz), 6.96 (2 H, t, J=7.9 Hz), 4.04 – 4.1 1 (2 H, m), 3.65 (2 H, dd, J=5.3, 3.8 Hz), 3.31 (3 H, s); Mass Spectrum (ESI) m/e = 281.0 [M+l].

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
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These common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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. Computed Properties of C7H8BrNO

(w) By proceeding in a similar manner to Reference Example 4(a), method A, but using cyclopropyl cyanide and 5-bromo-2-methoxyaniline (Reference Example 50), there was prepared 1-bromo-3-(cyclopropyl-imino-methylamino)-4-methoxybenzene.

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

Reference:
Patent; Rhone-Poulenc Rorer Limited; US6303600; (2001); B1;,
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Ether | (C2H5)2O – PubChem

Application of 363-47-3, These common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, 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 glacial acetic acid (4.0 mL) precooled to 5 C were added potassium thiocyanate (4.0 mmol) and 2,6-difluoro-p-anisidine (1) (1.0 mmol). The mixture was stirred vigorously while 1.1 mmol of bromine in 1.5 mL of glacial acetic acid was added drop-wise such that the temperature did not rise beyond 0 C. After all the bromine was added (60 min), the solution was stirred for another 2 h at 0 C and at ambient temperature for 10 h. It was allowed to stand overnight, during which a yellowish-orange precipitate settled out. Water (30 mL) was added and the solution was adjusted to pH 6 with sat aq NaHCO3. The mixture was extracted with dichloromethane (3 × 50 mL) and the combined extracts were dried over Na2SO4 and evaporated to give a yellowish-orange solid as the crude product. Flash chromatography using hexane:dichloromethane 2:3 gave a dark yellow solid in 56% yield.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pirrung, Michael C.; Biswas, Goutam; De Howitt, Natalie; Liao, Jiayu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 20; (2014); p. 4881 – 4883;,
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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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 349-55-3

EXAMPLE 68 Synthesis of 2-[(3-methoxy-5-(trifluoromethyl) phenyl)amino]phenylacetic Acid In the manner described in example 3, 2-bromophenylacetic acid is condensed with 3-methoxy-5-(trifluoromethyl)aniline to yield 2-[(3-methoxy-5-(trifluoromethyl)phenyl)amino]phenylacetic acid.

According to the analysis of related databases, 349-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Exocell, Inc.; US6355680; (2002); B1;,
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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, Computed Properties of C8H11NO

General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3).

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; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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Adding a certain compound to certain chemical reactions, such as: 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, 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 202865-80-3, SDS of cas: 202865-80-3

Potassium acetate (10.52 g, 107.2 mmol) and bis(pinacolato)diboron (15 g, 58.96 mmol) were added to a solution of intermediate 7 (10.52 g, 107.2 mmol) in dioxane (125 ml), and the solution was degassed for 30 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloro palladium(II) CH2Cl2 (4.4 g, 5.36 mmol) was added under nitrogen atmosphere and heated to 80 C. After 12 hours, the reaction mixture was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as a yellow oil (13.9 g, 99%) which was used without purification in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluoro-1-isopropoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; TG THERAPEUTICS, INC.; RHIZEN PHARMACEUTICALS SA; LABORATOIRE FRANCAIS DU FRACTIONNEMENT ET DES BIOTECHNOLOGIES; Weiss, Michael S.; Miskin, Hari P.; Sportelli, Peter; Vakkalanka, Swaroop K.V.S.; US2015/290317; (2015); A1;,
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Application of 41365-75-7, 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. 41365-75-7 name is 1-Amino-3,3-diethoxypropane, 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.

Intermediate 6; EPO To a solution of Intermediate 4 (1.40 g, 3.49 mmol), 1 -amino-2,3-diethoxypropane (513 mg, 3.49 mmol), and DIPEA (2.25 g, 17.45 mmol) in DMF (50 ml) was added HATU (1.592 g, 4.19 mmol). The solution was allowed to stand at RT for 2 h and the DMF was evaporated. The residue was partitioned between EtOAc (150 ml) and sat. aqueous NaHCO3 (200 ml). The organic layer was separated and the aqueous was extracted further with EtOAc (2 x 150 ml). The combined extracts were washed with water (200 ml), brine (100 ml), dried (Na2SO4) and evaporated. The crude product was purified on an lsolute SPE Si Il cartridge (20 g) eluting with 40-60% EtOAc in pentane and then 100% EtOAc to afford a cream solid.Yield: 1.59 g (86%)LC-MS (Method 3): Rt 3.06 min, m/z 553 [MNa]+

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

Reference:
Patent; ARGENTA DISCOVERY LTD.; WO2006/136857; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem