Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, SDS of cas: 1535-73-5

General procedure: An equimolar mixture of trifluoromethoxyaniline 1 or 2 (5.65 mmol) and the corresponding activated enol ether 3a-h was heated under reflux for 2-120 min (TLC detection). If necessary, methanol or ethanol was used as solvent. Once the reaction was complete, it was cooled to room temperature and the solids formed were separated by suction, washed with hexanes and dried to give enamines 4-5a-h. Isolated enamines 4-5a-h were characterized and used in the subsequent steps.

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Reference:
Article; Plevova, Kristina; Briestenska, Katarina; Colobert, Francoise; Mistrikova, Jela; Milata, Viktor; Leroux, Frederic R.; Tetrahedron Letters; vol. 56; 36; (2015); p. 5112 – 5115;,
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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. 102503-23-1, name is 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H15NO2

General procedure: N-(2,4-dimethoxybenzyl)-N-methyl-3-phenylprop-2-yn-1-amine (5a). CuI (20 mg, 0.10 mmol) was added to a solution of phenylacetylene(510.6 mg, 5.0 mmol), HCHO (36% aq., 2 mL),N-methyl(2,4-dimethoxybenzyl)amine (1.09 g, 6.0 mmol) in DMSO (10.0mL). The resulting yellow green solution was stirred at room temperatureovernight and then diluted with H2O (10 mL), extracted with Et2O (15 mL x 3). The combined extractswas washed with H2O (2 x), brine (2 x) respectively, dried over Na2SO4, filtered, concentrated. Theresultant yellow oil was purified through flash column chromatography (silica gel, EtOAc/Hex = 1:6 to1:3) to give the product (5a, 1.14 g, 96%).

According to the analysis of related databases, 102503-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Miao; Odelberg, Shannon J.; Tong, Zongzhong; Li, Dean Y.; Looper, Ryan E.; Tetrahedron; vol. 69; 27-28; (2013); p. 5744 – 5750;,
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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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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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Application of 867288-00-4, These common heterocyclic compound, 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, 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.

Procedure -1A solution of an anhydride (1.3 eq.) and an amine (1 eq) were dissolved in dioxane and refluxed overnight. Dioxane was evaporated and the resultant residue dissolved in AcOEt and extracted into aq. 2N NaHC03 solution. The aqueous layer was acidified with aq. 2 HC1 to obtain a solid, which was filtered and dried to give the desired amide.Example 12-(3^-Difluoro-3′-methoxybiphenyl-4-yIcarbainoyI)berizoic acid:The title compound (52 mg) was obtained from intermediate 1 (150 mg, 0.64 mmol) and phthalic anhydride (189 mg) as a white solid. MJ: 168-173G te-NMR (delta ppm, DUSO- k, 400 MHz): 13.05 (s, 1H), 10.19 (s, 1H), 7.83 (d, J 7.4, 1H), 7.69-7.63 (m, 1H), 7.62-7.52 (m, 4H), 7.39 (t, / 7.9, 1H), 7.34-7.27 (m, 2H), 6.98 (d, / 6.8, 1H), 3.83 (s, 3H). MS (m z): 381.55 ([itf-H]”).

The synthetic route of 867288-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCOZEN THERAPEUTICS PVT. LTD.; RHIZEN PHARMACEUTICALS SA; MUTHUPPALANIAPPAN, Meyyappan; BHAVAR, Prashnant, Kashinath; VISWANADHA, Srikant; VAKKALANKA, Swaroop, Kumar, V.S.; MERIKAPUDI, Gayatri, Swaroop; WO2011/138665; (2011); 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. 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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Adding a certain compound to certain chemical reactions, such as: 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, 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 4463-59-6, Recommanded Product: 1-(2-Bromoethoxy)-2-methoxybenzene

EXAMPLE 68 1-[2-(2-Methoxyphenoxy)ethyl]-4-benzamidopiperidine 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heated on a steam bath for 4 hr. The resultng mass was crushed and stirred in water (200 ml.) at 60 for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4. Analysis: Found: C, 64.74; H, 7.08; N, 7.14. C21 H26 N2 O3.HCl requires C, 64.52; H, 6.96; N, 7.17%.

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Reference:
Patent; John Wyeth & Brother Limited; US4029801; (1977); 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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 14804-31-0

After starting the Grignard reaction by adding 25.0 ml 4-bromo2-methyl-anisole to a mixture of 30.2 g (1.24 mol) magnesium turnings and 650 ml THF, 150 ml 4-bromo2-methylanisole (total: 175.0 ml were added at a pace sufficient to maintain reflux temperature. The reaction mixture was heated to reflux for additional 5 h, cooled to r.t. and dropped at 0 C. within 1 h to a stirred solution prepared by mixing 904 g (500 ml, 4.19 mol) 1,4-dibromo-butane in 1000 ml THF with a freshly prepared solution of 1.28 g (60.0 mmol) LiCl and 4.00 g (29.8 mmol) Cu(II)Cl2 in 140 ml THF. Stirring was continued for 12 h at r.t. followed by the addition of 400 ml of a 20% ammonium chloride solution and 200 ml ethyl acetate. The water phase was extracted twice with 250 ml ethyl acetate, all organic phases were combined, dried over sodium sulphate and evaporated. The resulting oil was fractionated by vacuum distillation. Yield: 226.3 g (71%), b.p. 131-134 C./0.01 mbar. 1H-NMR(400 MHz, D6-DMSO): delta=1.60(quintet, 2H, C2-CH2-Ph), 1.82(quintet, 2H, C2-CH2-Br), 2.23(s, 3H, CH3), 2.51(t, 2H, CH2-Ph), 3.55(t, 2H, CH2-Br), 3.70(s, 3H, OCH3), 6.67d, 1H, 5-H), 6.72(s, 1H, 3-H), 7.01(d, 1H, 6-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 14804-31-0.

Reference:
Patent; Hofmeister, Thomas; Reiff, Ulrike; von Hirschheydt, Thomas; Voss, Edgar; US2006/69095; (2006); A1;,
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Some common heterocyclic compound, 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, molecular formula is C9H13NO2, 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. category: ethers-buliding-blocks

The synthetic procedure used in this preparation is outlined in Scheme M. 4-(4-Fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (180 mg), 4,5-dimethoxy-2-methyl-phenylamine (86 mg) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 265 mg) were dissolved in 10 mL DMF, followed by 0.2 mL di-iso-propylethyl amine. The mixture was heated at 50 for 72 hours, then cooled, diluted with aqueous pH 2 buffer and ethyl acetate, and the layers separated. The organic layer was washed with saturated sodium bicarbonate and brine, then dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed in 3% MeOH/DCM. The fraction containing the product was washed with 10% aqueous HCl, and concentrated in vacuo to yield 52 mg of 4-(4-fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (4,5-dimethoxy-2-methyl-phenyl)-amide, MS (M+H)=430.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41864-45-3, its application will become more common.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; Walker, Keith Adrian Murray; US2011/28502; (2011); A1;,
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Electric Literature of 67191-35-9,Some common heterocyclic compound, 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, molecular formula is C11H14O, 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.

EXAMPLE 1 Metathesis by Ethenolysis of Methyl Oleate Catalyzed by a Type 3 Complex (FIG. 1) in an Ionic Liquid; 1 ml of 3-butyl-1,2-dimethylimidazolium bis-triflylamide with formula [BMMI]+[N(CF3SO2)2]- pre-dried overnight at 80 C., 148 mg of methyl oleate (source: Fluka, with a purity higher than 98%) and 15 mg of the complex with formula Cl2Ru(CH-o-O-iPrC6H4)PCy3 (synthesized by reacting the 1st generation Grubbs complex with formula Cl2Ru(CHC6H5)(PCy3)2 with 1-isopropoxy-2-vinylbenzene in the presence of CuCl), this corresponding to 5% molar of catalyst with respect to methyl oleate, were introduced, in an inert atmosphere of argon, into an autoclave reactor provided with an agitation system and a pressure sensor. The autoclave was then placed under vacuum and pressurized to obtain a pressure of 10 bars (1 MPa) of ethylene (origin: Alphagas, quality N25). The temperature was kept constant at 20 C. The medium was stirred at ambient temperature for 2 hours, then the excess ethylene was slowly purged by returning to atmosphere pressure at a temperature not exceeding 20 C. and the autoclave was again placed under an atmosphere of argon. The products were separated from the ionic liquid by adding 2 to 3 ml of heptane distilled over CaH2 and degassed. An aliquot (100 mul) of the extracted solution was passed through a short silica column (2 cm) eluted with diethyl ether. It was analyzed by gas phase chromatography (ZB-1 column, 100% dimethylpolysiloxane, 30 metres, helium vector gas 2 ml/min, temperature programming: 60 C. then 5 C./min to 220 C.) coupled to a mass spectrometer. The methyl oleate conversion was 95%. It was calculated using decane as an internal reference. The reaction products were composed of 1-decene (fraction A) and methyl decenoate (fraction B). The presence of 1-decene isomers was not detected. Homo-metathesis products were present in trace amounts and could not be quantified.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropoxy-2-vinylbenzene, its application will become more common.

Reference:
Patent; Olivier-Bourbigou, Helene; Vallee, Christophe; Hillion, Gerard; US2007/179307; (2007); A1;,
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