Category: 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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Methoxy-5-(trifluoromethyl)aniline

EXAMPLE 22 3-{4-[3-(2-Methoxy-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide 82.4 mg (0.278 mmol) of triphosgene, followed by 0.223 cm3 of triethylamine, are added, at a temperature in the region of 20 C., under an argon atmosphere, to 0.2 g (0.793 mmol) of 3-(4-aminophenyl)-1H-pyrrolo-[3,2-b]pyridine-2-carboxamide in solution in 18 cm3 of tetrahydrofuran. After stirring for 1 hour at a temperature in the region of 20 C., 182 mg (0.952 mmol) of 2-methoxy-5-trifluoromethylphenylamine in solution in 17 cm3 of tetrahydrofuran are added. After stirring for 16 hours at a temperature in the region of 20 C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give a residue which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile] (90/5/5 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 109 mg of 3-{4-[3-(2-methoxy-5-trifluoromethylphenyl)ureido]-phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide are obtained in the form of a yellow solid that melts at around 194 C.; 1H NMR (300 MHz, (CD3)2SO d6, -delta in ppm): 3.99 (s: 3H); 6.97 (broad s: 1H); from 7.18 to 7.27 (m: 2H); 7.33 (dd, J=9 and 1 Hz: 1H); 7.56 (d, J=9 Hz: 2H); 7.63 (d, J=9 Hz: 2H); 7.66 (very broad s: 1H); 7.81 (dd, J=8 and 1.5 Hz: 1H); 8.40 (dd, J=4.5 and 1.5 Hz: 1H); 8.58 (m: 2H); 9.56 (s: 1H); 11.88 (very broad s: 1H). MS-ES+: m/z=470(+)=(M+H) (+).

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; AVENTIS PHARMA S.A.; US2007/259910; (2007); A1;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 20781-20-8

General procedure: Amine (1 mmol), 2-aminothiophenol (2 mmol), BODIPY photosensitizer (0.01 mmol, 1.0 mol%), and acetonitrile (5 mL) were added to a dry 10-mL flask. The flask was pressurized with air (2 bar) and then heated to 50 C. The solution was then irradiated using a 35-W xenon lamp through a cutoff filter (0.72M NaNO2 aqueous solution, which is transparent for light >385nm, because lamps could emit a small amount of ultraviolet light). After the reaction was completed, the solvent was evaporated under reduced pressure. The crude product was further purified using column chromatography.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20781-20-8.

Reference:
Article; Zhou, Zeyin; Yang, Weijun; Synthetic Communications; vol. 44; 21; (2014); p. 3189 – 3198;,
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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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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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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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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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Adding a certain compound to certain chemical reactions, such as: 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, 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 126-38-5, HPLC of Formula: C5H11BrO2

1-bromo-2,2-dimethoxypropane (1a) (20 g, 109.27 mmol) was dissolved in chloroform (100 mL)Trifluoroacetic acid (74.75 g, 655.59 mmol) was added and reacted at room temperature for 4 hours.The reaction solution was added with dichloromethane (30 mL) and water (150 mL), and the layers were extracted. The organic phase was washed with saturated brine (100 mL x 4), dried over anhydrous sodium sulfate and concentrated at 30 C under reduced pressure to give the title compound Ib as a black oil (11 g, yield 73.5%).

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; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wei Yonggang; Qiu Guanpeng; Lei Bolin; Li Yao; Wang Song; Zhu Guozhi; (39 pag.)CN106279128; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, 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 74654-07-2, HPLC of Formula: C7H17NO3

A solution of methoxy-oligo(ethylene glycol) amine (2c-4c) (8.2 mmol, 1.0 eq.) and DMAP (2.00 g,16.4 mmol, 2.0 eq.) in acetonitrile (15 mL) was added dropwise to a solution of bis(4-nitrophenyl)carbonate (2.74 g, 9.0 mmol, 1.1 eq.) in acetonitrile (15 mL) and the resulting solution was stirred at50 C for 3 h. The reaction mixture was then diluted in DCM (150 mL) and washed with 0.5 N HCl(100 mL). The aqueous layer was washed with DCM (5 ¡Á 100 mL) and all the organic fractions werecollected, dried over MgSO4 and filtered. The solvent was evaporated under reduced pressure and theresidue was purified by flash chromatography. 4-Nitrophenyl (2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbamate (2c). Purified by flash chromatographyusing DCM/Acetone = 9:1 as eluent. 87% yield as a pale yellow oil. 1H-NMR (250 MHz, CDCl3) delta(ppm): 3.31 (s, 3H, -O-CH3), 3.37-3.43 (m, 2H, -O-CH2-CH2-NH-), 3.49-3.63 (m, 10H, 2 ¡Á-O-CH2-CH2-O- + -O-CH2-CH2-NH-), 6.06 (t, 1H, -NH-, 3JH-H = 5 Hz), 7.25 (d, 2H, Ar-H,3JH-H = 9.25 Hz), 8.15 (d, 2H, Ar-H, 3JH-H = 9.25 Hz); 13C-NMR (62.9 MHz, CDCl3) delta (ppm): 155.9,153.1, 144.3, 124.8, 121.8, 71.6, 70.2, 70.2, 69.9, 69.3, 58.7, 40.8; ESI-MS (ion trap): m/z 329 [M + H]+.HRMS (ESI+): m/z 329.1357 [M + H]+, calcd for C14H21N2O7: 329.1349.

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; Mattarei, Andrea; Azzolini, Michele; Zoratti, Mario; Biasutto, Lucia; Paradisi, Cristina; Molecules; vol. 20; 9; (2015); p. 16085 – 16102;,
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Related Products of 145903-31-7, These common heterocyclic compound, 145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine, 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.

Compound 1 is converted into compound 4 or its free base 4a as described in Example 1. To prepare compound 40, a mixture of compound 4 or its free base 4a, methyl 1-bromoacetate and pyridine are reacted in DMF for a suitable amount of time. To this mixture, ethyl acetate is added, and if necessary, the reaction mixture is washed with a basic solution (for example NaHCO3), or water. The product compound 39 (ARM110), as an oil, may be purified, for example by SiO2 column chromatography.

The synthetic route of 145903-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Shixian; Belvedere, Sandro; Yan, Jiaming; Landry, Donald; US2009/227788; (2009); A1;,
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Synthetic Route of 67191-35-9, A common heterocyclic compound, 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, molecular formula is C11H14O, 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 flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 849 mg 1b (1.00 mmol), 173 mg 2-isopropoxystyrene (1.05 mmol; 1.05 equiv) and 1026 mg Amberlyst 15-A resin in dry form (4.00 mmol; 4 equiv) was loaded into the reaction flask and 25 mL THF is added. The reaction was stirred at 40 C. for 1.5 hour, during which the reaction mixture colors from pink to green. Then, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the polystyrene sulfonic acid resin. Evaporation of all volatiles, suspending in 20 mL hexane and subsequent filtration and drying in vacuo afforded the desired compound 3b as a green air-stable product. 1H and 13C NMR analyses are in agreement with those found in literature.

The synthetic route of 67191-35-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GHENT UNIVERSITY; UMICORE AG & CO. KG; Monsaert, Stijn Frans; Verpoort, Francis Walter Cornelius; US2013/35494; (2013); A1;,
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