Tag: M.W=100-200

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 150-78-7 as follows. Quality Control of 1,4-Dimethoxybenzene

General procedure: To a stirred solution of starting compound (0.5-1.2 mmol) in DMF-H2O (95:5, v/v, 8-12 mL) mixture was added NBS (4.0-4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20%, 20-30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product.

According to the analysis of related databases, 150-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Natarajan, Palani; Vagicherla, Vinuta Devi; Vijayan, Muthana Thevar; Tetrahedron Letters; vol. 55; 24; (2014); p. 3511 – 3515;,
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Reference of 366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-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.

Cyclopentanone (16.8 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-Cyclopentyl-3-fluoro-4-methoxyaniline (2.0 g, 48percent yield). MS m/z=210 [M+H].

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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Synthetic Route of 402-52-8, 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. 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 17 3-14- [3- (2-BENZOYL-4-TRIFLUOROMETHYL-PHENOXY)-BUTOXY]-2-METHYL-PHENYLL-PROPIONIC acid Step A (2-Methoxy-5-trifluoromethyl-phenyl)-phenyl-methanone; A 1.6 M solution of n-BuLi in hexanes (0.51 mL, 0.82 mmol) is added dropwise for about 20 min to N, N, N, N-tetramethylenediamine (0.12 mL, 0. 80 mmol) at -20C UNDER N2 After 20 min, p-trifluoromethylanisole (0.10 g, 0.57 mmol) in THF (0.2 mL) is added dropwise for 15 min at-20 C under N2. After IH, N-methoxy-N-methyl- benzamide (0.12 mL, 0.79 mL) is added dropwise in 10 min AT-20 C UNDERN2. After 2h, a 1 M HCl (0.9 mL) is added. The mixture is extracted with EtOAc, and organic phases are combined and washed with saturated aqueous sodium chloride, and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography, silica, hexanes: EtOAc (90: 10) provides the title compound (0.09 g, 0.32 mmol, 57%): ES+ (M/E) 281.08 (M+H) + ; RR 0.20 hexanes : EtOAc (90: 10).

The chemical industry reduces the impact on the environment during synthesis 1-Methoxy-4-(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/19151; (2005); A1;,
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Synthetic Route of 437-82-1, A common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, 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.

5 g (34.7 mmol) of 2,6-difluoroanisole and 2.62 g (40 mmol) of cyclopropylnitrile are added in 100 ml of toluene. At room temperature, 77 ml of a 0.5 M solution of KHMDS in toluene is added in drops. The reaction mixture is heated slightly. After stirring overnight at room temperature, water and ethyl acetate are added. It is shaken with 10% sulfuric acid, and the organic phase is separated. After repeated shaking of the aqueous phase with ethyl acetate, the combined organic extracts are washed with brine. After drying on sodium sulfate, it is filtered off, and the solvent is spun off. After chromatography on silica gel (mobile solvent: ethyl acetate/hexane), 2.53 g (38.2%) of the desired compound is obtained.

The synthetic route of 437-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schmees, Norbert; Lehmann, Manfred; Rehwinkel, Hartmut; Strehike, Peter; Jaroch, Stefan; Schaecke, Heike; Schottelius, Amdt J.G.; US2004/209875; (2004); A1;,
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Synthetic Route of 64465-53-8, 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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example 1; 4-Bromo- 1 -fluoro-2-methoxybenzene; Aqueous hydrobromic acid (48%, 2.41 mL) was added to 4-fluoro-3-methoxyaniline (1.0 g, 7.1 mmol) in water (10 mL) and the resulting mixture was cooled to 0 0C in an ice bath. A solution of sodium nitrite (538 mg, 7.8 mmol) in water (5 mL) was added drop wise during 15 min while maintaining the temperature between 0-5 0C. The resulting diazoniumsalt solution was added to a suspension of copper (I) bromide (1.12 g, 7.8 mmol) in water (5 mL) which had been pre-heated to 75 C. The mixture was shaken thoroughly, aqueous hydrobromic acid (48%, 12.07 mL) was added and the solution was stirred at ambient temperature for 16 h. Excess water was added and the product was extracted with diethyl ether and the combined organic extracts were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, filtered and the solvent was evaporated in vacuo to give 1.02 g (70% yield) of the title compound: 1H-NMR (DMSO-afo): delta 7.36 (dd, J = 7.78, 2.26 Hz, 1 H), 7.23 – 7.17 (m, 1 H), 7.14 – 7.09 (m, 1 H), 3.86 (s, 3 H); MS (EI) m/z 204, 206 [M+«]

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/145568; (2007); A1;,
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Reference of 1579-40-4, A common heterocyclic compound, 1579-40-4, name is Di-p-tolyl Ether, molecular formula is C14H14O, 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.

General procedure: To the 250 mL 3-neck RB flask charged di-p-tolylether (10 g, 50.43 mmol), benzoicacid (7.39 g, 60.52 mmol) and ZnCl2 (19.73 g, 144.73 mmol) in POCl3 (15 mL)and stirred mechanically for few minutes. Then the reaction mixture heated up to95C and allowed to stir for 4h. After 4h, color of the reaction mixture turned intodark brown and unable to stir. Then the above reaction mixture cooled to 0C andquenched with crushed ice (40 g) while mechanically stirring. To the above reactionmixture added H2O (150 ml) and allowed to stir at RT for 16h.The obtainedsolid suspension filtered through Buchner funnel and the solid cake washed withH2O (3 × 50 mL) followed by hexane (2 × 100 mL) to get crude DMPx-OH. Thiscrude solid re-dissolved in EtOAc (200 mL) and taken into separating flask andwashed with sat NaHCO3 (2 × 50 mL), the organic layer dried over Na2SO4 andevaporated the solvent on rotary evaporator to get off-white color DMPx-OH 2(10.37 g, 68%).1H NMR (400 MHz, CDCl3) delta: 2.24 (s, 6H), 2.55 (s, 1H), 7.07 (m, 4H), 7.12 (t, J= 0.8 Hz, 2H), 7.19 (m, 1H), 7.29 (m, 2H), 7.40 (dd, J1 = 8.3, 1.1 Hz, 2H).MS: 285.6 (M +).

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; Penjarla, Srishylam; Prasad, S. Rajendra; Reddy, Dhande Sudhakar; Banerjee, Shyamapada; Penta, Santhosh; Sanghvi, Yogesh S.; Nucleosides, nucleotides and nucleic acids; vol. 37; 4; (2018); p. 232 – 247;,
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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. 4342-46-5, name is 4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

1200 mL of water was added to the autoclave.Turn on stirring,Add 40% Formamide 220g (2mol), After stirring for 10 minutes,1-amino-4-methoxycyclohexane 130 g (1 mol) was added,Then add ruthenium carbon catalyst 7g,Pass CO into the reactor,The pressure in the kettle reaches 0.2MPa,Raise the temperature to 50CInsulation 20hControl raw materials < 2%,The reaction is over,Cool down to 2530C,Dilute hydrochloric acid was added dropwise to the reaction solution.Adjust the pH to 5-6.There is a solid precipitated,Filter out products,The cake is shuffled onceObtained 169 g of cis-8-methoxy-1,3-diazaspiro[4,5]-indol-2,4-dione as a dry product.Yield 84.5%; According to the analysis of related databases, 4342-46-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; Henan Longhu Biological Co., Ltd.; Mu Kairui; Guo Shuai; Xu Caiyun; (11 pag.)CN107721996; (2018); A;,
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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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

(2S,4R)-4-hydroxy-l-(3-(2-(2-methoxyethoxy)ethoxy)benzoyl)-N-(4-(4-methylthiazol-5- yl)benzyI)pyrrolidine-2-carboxamide A mixture of (2S,4R)-4-hydroxy-l-(3-hydroxybenzoyl)-N-(4-(4-methylthiazol-5- yl)benzyl)pyrrolidine-2-carboxamide (55 mg, 0.13 mmol) and potassium carbonate (55 mg, 0.40 mmol) in DMF (0.8 mL) was treated with l-bromo-2-(2-methoxyethoxy)ethane (commercially available from for example Aldrich) (0.034 mL, 0.25 mmol) and the reaction stirred at 50C for 2.5 hours. Additional l-bromo-2-(2-methoxyethoxy)ethane (0.034 mL, 0.25 mmol) was added and the mixture stirred at 50C overnight. The product was subjected to purification by mass-directed automated preparative HPLC (formic acid modifier) to afford the title compound (40 mg, 0.074 mmol, 59 % yield) LCMS RT= 0.74 min, ES+ve m/z 540 [M+H]+.

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 54149-17-6.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
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Electric Literature of 36865-41-5, 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. 36865-41-5, name is 1-Bromo-3-methoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of Mg (911 mg, 37.5 mmol) and of iodine (one crystal) in dry THF (30 mL) was added dropwise 5% of the total amount of 1-bromo-3-methoxypropane (4.59 g, 30.0 mmol). The mixture was heated to reflux with the help of a heat gun until the Grignard formation had started. The rest of the 1-bromo-3-methoxypropane was added slowly, while an exothermic reaction proceeded. After the end of the addition, the reaction mixture was stirred under reflux for 20 min, and was allowed to cool to rt. This Grignard sol. (1M in THF, 23.5 mL, 23.5 mmol) was added dropwise to a mixture of 2-bromo-5-chloro-4-dimethoxymethyl-pyridine (2.50 g, 9.38 mmol) and Ni(dppp)Cl2 (495 mg, 0.938 mmol) in THF (50 mL) at 0 C. The reaction mixture was stirred at rt for 30 min, and was then heated to reflux for 2 h. The mixture was allowed to cool to rt, and was dissolved with EtOAc. This mixture was washed with aq. sat. NaHCO3. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane o EtOAc/heptane 1:1) yielded the title compound (1.51 g, 62%). LC-MS: tR=0.80 min; ES+: 260.15.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-methoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Actelion Pharmaceuticals, Ltd.; US2009/88457; (2009); 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., Product Details of 702-24-9

Step 2. [(4-Methoxybenzyl)methylamino]acetonitrile PMBN N CN I [00314] A solution of (4-methoxybenzyl)methylamine (125 g, 0.828 mol), chloroacetonitrile (75 g, 0.993 mol, 1.20 equiv) and N,N-diisopropylethylamine (134 g, 1.035 mol) in toluene (600 mL) was refluxed for 1 h. The mixture was cooled to room temperature and diluted with EtOAc (1.5 L). The solution was washed with H20 (3 x 750 mL), brine, dried over Na2S04, filtered and the solution concentrated under reduced pressure. The residual liquid was distilled to give 152 g (97percent) of [(4- methoxybenzyl)methylamino]acetonitrile (bp 128-135°, 2.0 Torr).

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; THE UNIVERSITY OF CHICAGO; GAJEWSKI, Thomas F.; SPRANGER, Stefani; LEUNG, Michael; WO2014/66834; (2014); A1;,
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