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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., Safety of 1-(3-Methoxyphenyl)-N-methylmethanamine

General procedure: To a solution of bromobenzoyl chloride (2 mmol) was added the corresponding N-methylaniline (2 mmol) followed by Et3N (2 mmol) in CH2Cl2 (10 mL) at 0 C. After a few minutes, the ice bath was removed and the reaction mixture was warmed up to room temperature and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2 × 15 mL). The organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluent or by trituration in a mixture of diethyl ether / petroleum ether to afford the desired compound.

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:
Article; Gargano, Emanuele M.; Allegretta, Giuseppe; Perspicace, Enrico; Carotti, Angelo; Van Koppen, Chris; Frotscher, Martin; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; PLoS ONE; vol. 10; 7; (2015);,
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Electric Literature of 592-55-2, 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 592-55-2 as follows.

Add 3 g of potassium hydroxide solid to a 250 mL flask, then add 30 mL of DMF and stir well. After the above system was stirred for 10 minutes, 2 g of compound 2 was added thereto, and then the system was stirred for 30 minutes. Subsequently, 1.38 mL of was added2-bromoethyl ether, the reaction 18 hours at room temperature. After the reaction was completed, the above system was poured into 400 mL of water and extracted with 400 mL of dichloromethane. The organic layer was dried with 4 g of anhydrous magnesium sulfate and the solvent was evaporated to give a white product in a yield of 81%.

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Yu Xiaoqiang; Tian Minggang; He Xiuquan; Zhang Ruoyao; (11 pag.)CN106632264; (2017); A;,
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Application of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-trifluoromethoxy-5-bromo-phenylamine (5.12 g, 20 mmol) in EtOH (50 niL) at 00C was added a solution of acetic anhydride (4.7 rnL, 50 mmol) in EtOH (10 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated to drieness and the solid was tritured with diethyl ether and filtered to give 5.64 g (95% yield) of N-(5-bromo-2-trifluoromethoxy-phenyl)-acetamide . 1H NMR (400 MHz, DMSO-d6) delta ppm: 2.11 (s, 3 H) 7.39 (m, 2 H) 8.21 (s, 1 H) 9.87 (s, 1 H); MS (ESI): 257 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; WO2009/71480; (2009); A2;,
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Application of 54149-17-6, A common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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.

1-(2-Bromo-ethoxy)-2-methoxy-ethane (107 mg, 0.58 mmol) was added to a suspension of 4- hydroxy-2-(4-methoxy-benzyl)-isoindole-1 ,3-dione (150 mg, 0.53 mmol) and potassium carbonate (200 mg, 1.4 mmol) in DMF (2 mL). After 3.5 hours, a catalytic amount of potassium iodide was added. After a further 17 hours, the mixture was warmed to 60C. After 3 hours, an additional amount of 1-(2-bromo-ethoxy)-2-methoxy-ethane (20 mg, 0.11 mmol) was added and the mixture maintained at 6O0C for a further 20 hours. The mixture was concentrated in vacuo then the residue was taken up in ethyl acetate and washed with potassium carbonate solution and brine. The organic phase was dried (MgSO4) and concentrated to give the title compound as a yellow oil (149 mg, 73%). 1H NMR (methanol-d4) 7.71 (1 H, t), 7.43-7.40 (2H, m), 7.31-7.27 (2H, m), 6.87-6.83 (2H, m), 4.71 (2H, s), 4.37-4.34 (2H, m), 3.92-3.89 (2H, m), 3.77-3.74 (5H, m), 3.55-3.53 (2H, m), 3.33 (3H, s). MS: [M+H]+ 386.

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 437-83-2, name is 3-Fluoro-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 437-83-2, name: 3-Fluoro-2-methoxyaniline

Example 91 8-Ethyl-2-(3-fluoro-2-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one A mixture of 8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (133 mg, 0.56 mmol) and 500 muL of 3-fluoro-2-methoxyaniline was heated at 175 C. for 20 minutes. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluding with ethyl acetate. Recrystallization from ethyl acetate and hexane provided 28 mg (16%) of 8-ethyl 2-(3-fluoro-2-methoxyplhenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 92-93 C. Analysis calculated for C16H15N4O2F 0.15 H2O: C, 60.63; H, 4.83; N, 17.68. Found: C, 60.31; H, 4.52; N, 17.42.

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-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Booth, Richard John; Chatterjee, Arindam; Malone, Thomas Charles; US2004/224958; (2004); 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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 349-65-5

To a solution of 2-methoxy-5-(trifluoromethyl)aniline (0.15 g) in anh CH2Cl2 (15 mL) at 0 C. was added CDI (0.13 g). The resulting solution was allowed to warm to room temp. over 1 h, was stirred at room temp. for 16 h, then was treated with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.18 g). The resulting yellow solution was stirred at room temp. for 72 h, then was treated with H2O (125 mL). The resulting aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated (90% EtOAc/10% hexane). The resulting white solids were collected by filtration and washed with EtOAc. The filtrate was concentrated under reduced pressure and the residual oil purified by column chromatography (gradient from 33% EtOAc/67% hexane to 50% EtOAc/50% hexane to 100% EtOAc) to give N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a light tan solid (0.098 g, 30%): TLC (100% EtOAc) Rf 0.62; 1H NMR (DMSO-d6) delta2.76 (d, J=4.8 Hz, 3H), 3.96 (s, 3H), 7.1-7.6 and 8.4-8.6 (m, 11H), 8.75 (d, J=4.8 Hz, 1H), 9.55 (s, 1 H); FAB-MS m/z 461 ((M+H)+).

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2002/165394; (2002); A1;,
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Synthetic Route of 41789-95-1, 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. 41789-95-1 name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

The title compound was prepared by reaction of 4-bromobenzoylchloride (329 mg, 1.5 mmol) and 3-methoxybenzylamine (227 mg, 1.5 mmol) in presence of triethylamine (0.24 ml, 1.73 mmol) according to method A. Purification by FC (n- hexane/ ethyl acetate 6 : 1) afforded the desired product (468 mg, 93%); MS (ESI) : 335 (M + H)+; *H N MR (CD3COCD3) : 2.80-2.92 (m, 3H), 3.80 (s, 3H), 4.52-4.69 (m, 2H), 6.79 (br s, 1 H), 6.86 (dd, J= 8.5, 2.2 Hz, 1 H), 6.95 (br s, 1 H), 7.28 (t, J= 7.9 Hz, 1 H), 7.44 (d, J= 7.9 Hz, 2H), 7.62 (br s, 2H); 13C NMR (CD3COCD3) : 55.3, 112.9, 113.6, 120.0, 123.1, 129.1, 129.4, 130.0, 131.7, 135.7, 139.1, 159.8.

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

Reference:
Patent; UNIVERSITAeT DES SAARLANDES; HARTMANN, Rolf; MARCHAIS-OBERWINKLER, Sandrine; XU, Kuiying; WERTH, Ruth; WO2012/117097; (2012); A1;,
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Some common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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: 4-Fluoro-2-methoxyaniline

Taking 200 ml 98 wt % sulfuric acid is added to a 500 ml three-port flask, ice water bath cooled to 5 – 10 C, then addition of 2 – methoxy -4 – fluoro aniline (41.0g, 0 . 29 muM), control of speed of addition, the reaction solution maintained at a temperature of 0 – 20 C; then adding KNO batch3(34.4g, 0 . 34 muM), keep the temperature of the reaction solution is 0 – 20 C, after adding the reaction liquid natural temperature to 25 C, reaction 2h end after. The reaction liquid slowly poured into the 1L the ice water, stirring after filtering out the solid, the filtrate 40 wt % NaOH to pH=9 and in, dropwise lye process is maintained in the temperature not higher than 40 C, after adding stirring 1h, separating solid, after the solid is filtered, washed with water solid to neutral, then dried to obtain the brown body solid 2 – methoxy -4 – fluoro -5 – nitroaniline 40.5g, yield is 75.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 450-91-9, its application will become more common.

Reference:
Patent; Shanghai University of Engineering Science; Sun, Mingchen; Mao, Yongjun; Zhang, Rui; Liu, Xiangyu; Wang, Han; (14 pag.)CN106366022; (2017); A;,
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Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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: 6358-77-6

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 259 mg, 1.28 mmol), (3-chloro-2-methylphenyl)boronic acid (Combi-Blocks Inc., 240 mg, 1.41 mmol), 1,l’-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (209 mg, 0.26 mmol), and purged with nitrogen. 1,4-Dioxane (9.60 ml) and an aqueous sodium carbonate solution (1.9 M, 3.20 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-2′-methyl-[1,1′-biphenyl]-3-amine (226 mg, 0.91 mmol, 71.3 % yield) as a tan solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6358-77-6, its application will become more common.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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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. 2398-37-0, name is 1-Bromo-3-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 2398-37-0

General procedure: Compound 6a was prepared by reacting 3-bromo-2-methyl-5-thienylboronic acid [50] (4.2 g, 19.0 mmol) with 1-bromo-2-methoxybenzene (3.91 g, 20.9 mmol) in the presence of Pd(PPh3)4 (0.73 g, 0.63 mmol) and Na2CO3 (2 mol L-1, 10 mL) in tetrahydrofuran (THF) (80 mL) for 18 h at 343 K. The reaction was allowed to cool to room temperature. After being extracted with ether, the organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using petroleum ether as eluent to afford 3.87 g of 6a visible as a buff solid with a 72% yield.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Chunhong; Pu, Shouzhi; Pang, Zhiyi; Chen, Bing; Liu, Gang; Dai, Yanfeng; Dyes and Pigments; vol. 98; 3; (2013); p. 565 – 574;,
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