Ethers-buliding-blocks

Application of 2393-23-9, A common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, molecular formula is C8H11NO, 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.

1.1. Synthesis of bis-(4-methoxy-benzyl)-amine (Int. 1) p-Anisaldehyde (411 mmol), 4-methoxybenzylamine (411 mmol) and toluene (500 mL) were combined in a round bottomed flask fitted with a condenser and a Dean-Stark trap. The reaction was refluxed for 1 h during which water was removed from the reaction mixture. The reaction was cooled and concentrated. The residue was dissolved in MeOH (120 mL). The mixture was cooled to 5 C. and NaBH4 (205 mmol) was added in portions over 45 min. The reaction was slowly heated to reflux. After 2 h at reflux, the reaction was cooled to room temperature and concentrated. The residue was dissolved in EtOAc. The organic layer was washed (3*H2O and brine), dried (Na2SO4) and concentrated to yield the desired product.

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; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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Electric Literature of 645-36-3, 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 645-36-3 as follows.

N- (2-chloropyridine-4-substituted) -4-fluorobenzamide (5g, 19.9mmol) was dissolved in toluene (50mL), cooled to 0 C, and dichlorosulfoxide was slowly added dropwise under nitrogen protection. (7.1 g, 59.8 mmol), transferred to room temperature for 1 hour, and then refluxed overnight. TLC monitoring. After the reaction was completed, the solvent and dichlorosulfoxide were removed to obtain (Z) -N- (2-chloropyridine-4-substituted) -4-fluorobenzimidyl chloride.Dissolve aminoacetaldehyde diethanol (3.5 g, 23.9 mmol) and TEA (4.0 g, 39.8 mmol) in dichloromethane (100 mL), cool to 0 C, and obtain (Z) -N- (2-chloropyridine-4-substituted) -4-fluorobenzimidyl chloride was dissolved in dichloromethane (100 mL), and the solution was slowly added dropwise. The mixture was naturally warmed to room temperature and stirred overnight. Monitored by TLC. After the reaction was completed, the mixture was washed with a saturated ammonium chloride aqueous solution and a saturated saline solution, dried over anhydrous Na2SO4, filtered, and dried. Purification by silica gel column chromatography gave a yellow solid (7 g, 95.7%).

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Southern Medical University; Zhang Jiajie; Yang Haikui; Wu Shaoyu; Tian Yuanxin; Wan Shanhe; Zhang Tingting; Wu Xiaoyun; Li Zhonghuang; Jiang Ying; Yan Ruohong; Zhu Zhengguang; Hu Xiang; (75 pag.)CN110041302; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, Application In Synthesis of (Triethoxymethyl)benzene

To a suspension of triol 11 (3.0 g, 9.2 mmol) in dry MeCN (100 mL), camphor-10-sulfonic acid (880 mg, 3.7 mmol) and triethylorthobenzoate (8.2 mL, 38.6 mmol), were added. The mixture was stirred at rt for 12 h and Et3N (1.5 mL) was added to neutralize the solution. The mixture was then evaporated to dryness and the residue was diluted with DMF (100 mL). NaH (60percent dispersion in mineral oil, 542 mg, 18.4 mmol) was added at 0 °C followed by dropwise addition of BnBr (1.8 mL, 16.6 mmol). The reaction mixture was stirred at rt for 2 h and the excess of sodium hydride was neutralized by dropwise addition of MeOH (20 mL) at 0 °C. The mixture was then evaporated to dryness and the residue was dissolved with EtOAc. The organic phase was washed with water and then with 2 M aqueous HCl (.x.3). The opening of the orthoester was checked by TLC. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using cyclohexane/EtOAc (98:2–>9:1) as eluent to give 5 (2.2 g, 46percent) and its beta-anomer 2-methyl-5-tert-butylphenyl 2-O-benzoyl-4-O-benzyl-1-thio-beta-l-rhamnopyranoside (340 mg, 7percent) as colorless oils. (alpha anomer) Rf 0.42 (cyclohexane/EtOAc 8:2); [alpha]D -93 (CHCl3, c 0.7); 1H NMR (300 MHz, CDCl3) delta 8.24-7.27 (m, 13H, SC6H3C(CH3)3CH3, OCH2C6H5, OCOC6H5), 5.82 (dd, 1H, J1,2 = 1.3 Hz, J2,3 = 3.3 Hz, H-2), 5.66 (br s, 1H, H-1), 5.11 (d, 1H, JA,B = 11.2 Hz, A part of an AB system, OCHHC6H5), 4.93 (d, 1H, JA,B = 11.2 Hz, B part of an AB system, OCHHC6H5), 4.55-4.43 (m, 2H, H-3, H-5), 3.78 (t, 1H, J3,4 = J4,5 = 9.2 Hz, H-4), 2.59 (s, 3H, SC6H3C(CH3)3CH3), 1.59 (d, 3H, J5,6 = 5.9 Hz, H-6), 1.46 (s, 9H, SC6H3C(CH3)3CH3); 13C NMR (75 MHz, CDCl3) delta 166.4 (OCOC6H5), 149.8, 138.4, 137.0, 133.5, 133.0, 132.9, 130.2, 130.1, 130.0, 129.7, 128.7, 128.6, 128.5, 128.3, 128.1, 127.6, 125.2, 124.0, (SC6H3C(CH3)3CH3, OCOC6H5, OCH2C6H5) 85.8 (C-1), 81.8 (C-2), 75.6 (C-4), 75.3 (OCH2C6H5), 71.3 (C-3), 69.0 (C-5), 34.6 (SC6H3C(CH3)3CH3) 31.5 (SC6H3C(CH3)3CH3), 20.5 (SC6H3C(CH3)3CH3), 18.3 (C-6); HR-ESI-MS m/z calcd for C31H36O5S 543.2175 [M+Na]+, found 543.2160.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Conference Paper; Milhomme, Ophelie; Dhenin, Sandrine G.Y.; Djedaini-Pilard, Florence; Moreau, Vincent; Grandjean, Cyrille; Carbohydrate Research; vol. 356; (2012); p. 115 – 131;,
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Reference of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 a solution of 35 g of P8 in 354 ml of MeOH (methanol) was added 3.5 ml of AcOH (acetic acid). The solution was mixed with 33 ml of aminoacetaldehyde diethylacetal at room temperature and stirred for 3-4 hrs. After the solution was cooled to 10 s C, 3.3 g of the reducing agent NaBH4 (sodiumborohydride) was slowly added thereto. At this time, care had to be taken because of hydrogen gas generation and exothermal reaction. The solution was stirred at room temperature for 1 hr. When the reaction was completed, 354 ml of EA (ethylacetate) and 354 ml of distilled water were added so as to separate layers. The organic layer thus formed was dried over 141 g of MgSO4 (magnesium sulfate) and crystallized in hexane to afford 85 g of P7 as a yellowish solid (yield 80%) . 1H NMR (500MHz, CDCl3), delta 8.36 (d, J=4.8 Hz, IH), delta 7.61 (s, IH), delta 7.17 (d, J=4.2 Hz, IH), delta 7.10 (d, J=4.2 Hz, IH), delta 4.58 (t, J=3.3, IH), delta 4.21 (s, 3H), delta 4.07 (s, 3H), delta 3.68 (m, 2H), delta 3.51 (m, 2H), delta 2.82 (d, J=3.3 Hz, 2H), delta 2.48 (s, 3H), delta 1.19 (t, J=4.2 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Diethoxyethanamine, its application will become more common.

Reference:
Patent; CHOONGWAE PHARMA CORPORATION; WO2010/120112; (2010); A2;,
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Reference of 102-52-3,Some common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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.

100 mg (0.215 mmol) of Example 12 A were mixed with 1.00 mL (6.07 mmol) 1, 1,3,3- tetramethoxypropane. The reaction mixture was heated to 175C for lh using a microwave oven. The reaction mixture was treated with DCM/MeOH and one drop of triethylamine. The solvents were removed under reduced pressure. The mixture was purified by preparative HPLC (eluent A: water + 0.13 % TFA, eluent B: MeOH) yielding 45 mg (54 %) of the title compound.HPLC-MS (Method 3): R, = 1.36 minMS (ESI pos): m/z = 387 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,3,3-Tetramethoxypropane, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (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. 1535-73-5, name is 3-Trifluoromethoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Example 32 7-(2,4-dimethoxypyrimidin-5-yl)-4-((3-(trifluoromethoxy)phenyl)amino)quino sulfonamide To a suspension of 4-chloro-7-(2,4-dimethoxypyrimidin-5-yl)quinoline-3- sulfonamide (50 mg, 0.131 mmol) in acetic acid (10 ml.) was added 3- (trifluoromethoxy)aniline (23.26 mg, 0.131 mmol). The reaction mixture was stirred at room temperature overnight and was purified by reverse-phase preparative HPLC (YMC 75 X 30 mm column, acetonitrile/water + 0.1 percent trifluoroacetic acid) to afford 7-(2,4- dimethoxypyrimidin-5-yl)-4-((3-(trifluoromethoxy)phenyl)amino)quinoline-3-sulfonamide, trifluoroacetic acid salt (24 mg, 0.038 mmol, 28.8 percent yield) as a yellow solid. 1 H NMR (400 MHz, METHANOL-d4) delta ppm 4.08 (s, 3 H) 4.12 (s, 3 H) 7.37 – 7.48 (m, 3 H) 7.60 – 7.75 (m, 3 H) 8.28 (s, 1 H) 8.53 (s, 1 H) 9.16 (s, 1 H). LCMS (ES+) m/e 522 [M+H]+.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
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Related Products of 2398-37-0, The chemical industry reduces the impact on the environment during synthesis 2398-37-0, name is 1-Bromo-3-methoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.

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

Reference:
Article; Obermoser, Victoria; Mauersberger, Robert; Schuster, Daniela; Czifersky, Monika; Lipova, Marina; Siegl, Monika; Kintscher, Ulrich; Gust, Ronald; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 590 – 603;,
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Application of 24599-58-4,Some common heterocyclic compound, 24599-58-4, name is 2,5-Dimethoxytoluene, molecular formula is C9H12O2, 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-Bromo-5-methylcyclohexa-2,5-diene-1,4-dione (23). To a solution of toluquinol (1) (2.5 g, 20.14mmol,1.0 equiv.) in acetone (15 mL) was added K2CO3 (14 g, 100.70 mmol, 5.0 equiv.) and Me2SO4 (5.7 mL,60.41 mmol, 3.0 equiv.) and the reaction mixture was stirred for 3 h. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O. The organic phasewas washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressureto obtain the corresponding dimethoxy derivative (~20 mmol), which was used in the next stepswithout purification. To a solution of the dimethoxy derivative obtained above (~20 mmol) and NaOAc(3.3 g, 40.28 mmol, 2.0 equiv.) in AcOH (20 mL) was added bromine (1.2 mL, 2.15 mmol, 1.1 equiv.)over 25 min and, after the addition, the reaction mixture was stirred for 1 h. Then, the reaction mixturewas quenched by a slow addition of a saturated aqueous NaHCO3 solution at 0 C. The aqueousphase was then extracted with EtOAc and the organic phase washed with brine, dried over MgSO4,ltered, and the solvent removed under reduced pressure to obtain the corresponding bromo derivative(~20 mmol), which was used in the next step without purication. The bromo derivative obtainedabove (~20 mmol) was dissolved in CH3CN (35 mL). Then, CAN (28 g, 50.34mmol, 2.5 equiv.) and H2O(20 mL) were added and the reaction mixture was stirred for 1 h at 25 C. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O twice. The combinedorganic phases were washed with brine, dried over MgSO4, filtered, and the solvent removed underreduced pressure. The residue was purified by flash column chromatography (silica gel, 1% EtOAc inhexanes) to obtain compound 23 (1.5 g, 37% over 3 steps) as an orange solid [13]: Rf = 0.45 (silica gel,20% EtOAc in hexanes); 1H NMR (400 MHz, CDCl3) delta 7.29 (s, 1 H), 7.26 (s, 2 H), 2.08 (d, J = 1.6 Hz,3 H); 13C NMR (100 MHz, CDCl3) delta 185.1, 179.5, 146.5, 138.1, 137.5, 132.6, 15.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dimethoxytoluene, its application will become more common.

Reference:
Article; Cheng-Sanchez, Ivan; Torres-Vargas, Jose A.; Martinez-Poveda, Beatriz; Guerrero-Vasquez, Guillermo A.; Medina, Miguel Angel; Sarabia, Francisco; Quesada, Ana R.; Marine Drugs; vol. 17; 9; (2019);,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-(Difluoromethoxy)aniline

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 × 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
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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. 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C10H14O2

5.2. Formylation of Dimethoxybenzenes by Means of the Duff Reaction1 equivalent of dimethoxybenzene was dissolved in 20 ml of TFA and 1.05 equivalents or urotropin were added to the resulting solution. The reaction mixture was brought to reflux for 2 hours under anhydrous conditions. The TFA was evaporated off under reduced pressure, the residue was dissolved in 100 ml of ether and the organic solution was washed with water (3 times 50 ml) and then dried over MgSO4. The solvent was evaporated off and the residue was subjected to column chromatography, elution being carried out with an 80:20 mixture of light mineral spirit (60-80 C.):diethyl ether.5.2.1. 2,5-Dimethoxy-3,4-dimethylbenzaldehydeThe process was carried out as described in point 5.2 above, using 2.270 g (0.01366 mol) of 1,4-dimethoxy-2,3-dimethylbenzene. The title product was isolated in the form of a white solid (1.18 g, 44%).

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; bioMerieux; US7626018; (2009); B2;,
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