Ethers-buliding-blocks

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. 4179-19-5, name is 3,5-Dimethoxytoluene, A new synthetic method of this compound is introduced below., Computed Properties of C9H12O2

To a solution of l,3-dimethoxy-5-methylbenzene (4 g, 26.28 mmol) in ACN (60 mL) at 0 C was added Selectfluor (8.4 g, 23.73 mmol) drop wise with stirring. The resulting solution was stirred overnight at room temperature and then quenched with water. The resulting solution was extracted with DCM and the organic layers combined and concentrated. The residue was purified by chromatography (ethyl acetate/pet. ether (1 :20)) to afford 1.5 g (34%) of 2-fluoro- l,5-dimethoxy-3-methylbenzene as colorless oil.

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; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth Albert; VERNER, Erik; (122 pag.)WO2016/191172; (2016); A1;,
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Related Products of 6358-77-6, 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.

A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, Recommanded Product: 22236-10-8

Example 1Synthesis of compound Ia-1Step 1 Compound 1 (3.44 g, 15.0 mmol) in N,N’-dimethylformamide (20 mL) at room temperature was added with 4-difluoromethoxyaniline (2.23 mL, 18.0 mmol), HOBt (2.63 g, 19.5 mmol) and EDC hydrochloride (3.45 g, 18.0 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was poured into 0.05 N hydrochloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, and dried over magnesium sulfate, and then, the solvent was removed in vacuo. The residue was added with ethyl acetate and hexanes, and the precipitated crystals were collected by filtration to give the desired amide compound 2 (3.88 g, yield 70%).

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, 4-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIONOGI & CO., LTD.; US2011/319412; (2011); A1;,
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Application of 6096-89-5, 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 6096-89-5 as follows.

l,r-Carbonyldiimidazole (162 mg, 1.00 mmol) was added to a solution of 0-1 -(3 -(trifluorometliyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (78.0 mg, 0.50 mmol) and triethylamine (101 mg, 1.00 mmol) in CH2Cl2 (15 ml) and stirred at room temperature for 24 hours. 2-(4-fluorophenoxy)ethanamine (162 mg, 0.50 mmol) was added to the reaction mixture and stirred at room temperature for another 17 hours. The reaction mixture was diluted with CH2Cl2 (50 ml) and washed with aqueous 0.1 N HCl solution (20 ml), H2O (30 ml x 3) and brine (30 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative TLC (ethyl acetate/petroleum ether: 67/33) to give L1 (2-(4-fluorophenov)ethyl-3 -( 1 -(3 -(trifluoromethyl)phenylsulfonvDpiperidin-4-yloxy)urea (80 mg, 32%) as a white solid: LCMS: 506 [M+lf. 1H NMR (DMSO-d6) delta: 1.68 (t, 2H), 1.87 (t, 2H), 2.83 (t, 2H), 3.20 (d, 2H), 3.37 (m, 2H), 3.62 (d, IH), 3.94 (2H, t), 6.84 (t, IH), 6.93 (m, 2H), 7.09 (t, 2H), 7.91 (t, IH)5 7.97 (s, IH), 8.07 (d, IH), 8.13 (d, IH), 9.01 (s, IH).

According to the analysis of related databases, 6096-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIONOGI & CO., LTD.; WO2009/151152; (2009); 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 450-88-4 as follows. Quality Control of 1-Bromo-4-fluoro-2-methoxybenzene

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 1-Bromo-4-fluoro-2-methoxybenzene was borylated using the general procedure described above. After workup, a white solid was obtained (0.313 g, 95%): mp 104-105 C.; 1H NMR (500 MHz, CDCl3) delta 7.89 (d, J=6.5 Hz, 1H), 6.61 (d, J=11.0 Hz, 1H), 3.72 (s, 3H), 1.35 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 167.6 (d, J=251.2 Hz), 159.5 (d, J=11.4 Hz), 140.2 (d, J=10.4 Hz), 108.3 (d, J=22.7 Hz), 105.9 (d, J=2.9 Hz), 83.9, 56.4, 24.8; 19F NMR (470 MHz, CDCl3) delta 100.4; 1113 NMR (160 MHz, CDCl3) delta 29.5 (br s).

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
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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. 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 41864-45-3

The compound 68 (150 mg, 0.415 mmol) was dissolved in acetic acid (0.75 mL). 4,5-dimethoxy-2-methylaniline (84 mg, 0.501 mmol) was added to the solution. The mixture was stirred at 100C for 3 hours. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (ethyl acetate-n-hexane) to give the compound 1-1252 (112 mg, yield 56%). 1H-NMR (DMSO-D6) delta: 1.24 (t, J = 7.2 Hz, 3H), 1.98 (s, 3H), 3.69 (s, 3H), 3.74 (s, 3H), 4.26 (q, J = 6.8, 14.0 Hz, 2H), 5.37 (s, 2H), 6.76 (s, 1H), 6.83 (s, 1H), 7.36 (dd, J = 6.8 Hz, 2H), 9.05 (s, 1H).

The synthetic route of 41864-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd; TANAKA, Satoru; OGAWA, Tomoyuki; KAI, Hiroyuki; OGATA, Yuki; HIRAI, Keiichiro; KUROSE, Noriyuki; FUJII, Yasuhiko; (438 pag.)EP3287443; (2018); A1;,
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Some common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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. COA of Formula: C9H13NO

Respectively, weighed o-iodobenzoic acid 252 mg,N-methyl-4-methoxybenzylamine 68 mg was added to 10 ml of chloroform,The reaction was stirred under reflux for 6 hours.Natural cooling to room temperature after pumping to remove IBX And its reduction products o-iodo benzoic acid(IBA),The filtrate was washed with 10percent Na0H solution,1M hydrochloric acid, water and saturated sodium chloride solution were washed 3 times,Each about 10 ml,The solvent chloroform was removed by rotary evaporation,The product was directly characterized by NMR, and the yield of 4-methoxybenzaldehyde was 91percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 702-24-9, its application will become more common.

Reference:
Patent; Guizhou University; CONG, Hang; WANG, Fang; TAO, Zhu; (8 pag.)CN105732351; (2016); A;,
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Synthetic Route of 645-36-3, A common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 (505 muL, 3.48 mmol) and Et3N (485 muL,3.48 mmol) were added to a soln of pyrimidine 3 (0.5 g, 2.32 mmol)in MeOH (25 mL), and the mixture was stirred at r.t. for 20 h. H2O(100 mL) was added and the precipitate was collected by filtration,dried, and crystallized (hexane) to give a colorless solid; yield: 0.62g (82%); mp 84-85 C.IR (KBr): 3320 (NH), 2220 (CN) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.26 (t, J = 6.9 Hz, 6 H, 2 ¡Á CH3),2.53 (s, 3 H, SCH3), 3.58 (dq, 2J = 9.6 Hz, 3J = 6.9 Hz, 2 H,2 ¡Á CHAHBCH3), 3.69 (t, J = 5.4 Hz, 2 H, NCH2), 3.76 (dq, 2J = 9.6Hz, 3J = 6.9 Hz, 2 H, 2 ¡Á CHAHBCH3), 4.02 (s, 3 H, OCH3), 4.61 (t,J = 5.4 Hz, 1 H, OCH), 5.65 (t, J = 5.4 Hz, 1 H, NH).13C NMR (75 MHz, CDCl3): delta = 14.5, 15.6, 43.8, 54.9, 63.3, 70.6,100.7, 114.7, 162.8, 169.7, 175.6.Anal. Calcd for C13H20N4O3S: C, 49.98; H, 6.45. Found: C, 50.08;H, 6.59.

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;,
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Reference of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Synthesis of2-chloro-5-methoxy-N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine [0342] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 28.08 mmol) in tertiary butyl alcohol (35 mL) under argon atmosphere were added 2-(trifluoromethoxy) aniline (4 g, 22.47 mmol) and diisopropylethylamine (35 mL) at RT. The reaction mixture was stirred at 160 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 10% EtOAc:hexanes to afford 2-chloro-5-methoxy- N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine (2 g, 22%) as a colorless syrup. 1H-NMR (CDCls, 400 MHz): delta 8.64 (d, 1H), 7.79 (s, 1H), 7.72 (br s, 1H), 7.38 (t, 1H), 7.30-7.27 (m, 1H), 7.10-7.07 (m, 1H), 4.00 (s, 3H); LC-MS: 320.3 (M+l); (column; X Select CSH C-18 (50 x 3.0 mm, 3.5 muiotaeta); RT 4.63 min. 0.05% Aq TFA: ACN; 0.80 ml/min); TLC: 15% EtOAc:hexanes {Rf. 0.3).

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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 349-65-5, Computed Properties of C8H8F3NO

To a solution of phosgene (1.93 M in toluene; 16 mL, 31.4 mmol) in CH2Cl2 (120 mL) at 0 C was added a solution of 2-methoxy-5-(trifluoromethyl)aniline (3.0 g, 15.7 mmol) and pyridine (2.3 mL, 47.1 mmol) in CH2Cl2 (30 mL) dropwise. The resulting mixture was stirred at 0 C for 30 min and at room temp for 3 h, then concentrated under reduced pressure. The residue was diluted with toluene (30 mL), concentrated under reduced pressure, and treated with Et2O. The resulting precipitate (pyridinium hydrochloride) was removed and the filtrate was concentrated under redeuced pressure to give the title compound as a yellow oil (3.0 g) which crystallized upon standing at room temp. for a few days.

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; Bayer Corporation; EP1449834; (2004); A2;,
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