Month: June 2021

Synthetic Route of 2930-05-4, 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. 2930-05-4 name is 2-((Benzyloxy)methyl)oxirane, 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.

General procedure: In a typical procedure, an admixture comprising of a solid cata-lyst (20 mg), an aryloxy epoxide (1 mmol) and an amine (1 mmol)were taken in a 5 mL screw capped vial and stirred vigorously fora given time period (monitored by TLC) under solvent free con-dition. At the end of the reaction, products amino alcohols wereobtained as viscous liquids or solids. Therefore, the reaction mix-ture was repeatedly washed with methanol (3 mL) and centrifuged.Methanol from the combined organic layer was evaporated underreduced pressure to get crude amino alcohol. A small sample of thecrude product was subjected to HPLC to find out regioselectivity,while rest of the reaction mixture was subjected to flash columnchromatography (hexane/ethyl acetate, 90:10) to get the majorregioisomer in pure form. The purified product was characterizedby1H and13C NMR, FTIR, Microanalysis and characterization datafor all the ring opening products are given in supporting informa-tion. The residue obtained from centrifugation was dried in air (1 h)and then in oven at 100C for 3 h to get back the catalyst (>97%recovery) for further use.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-((Benzyloxy)methyl)oxirane, and friends who are interested can also refer to it.

Reference:
Article; Shah, Arpan K.; Prathap, K. Jeya; Kumar, Manish; Abdi, Sayed H.R.; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 469; (2014); p. 442 – 450;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Fluoro-2-methoxybenzene

Step 1. Preparation of 3′-fluoro-4′-methoxyacetophenone Aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution was added acetyl chloride (51.0 g, 0.65 mol) dropwise, maintaining the temperature between 5-10 C. The mixture was allowed to stir for 10 minutes at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (63.06 g, 0.5 mol. The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with methylene chloride (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over magnesium sulfate, and concentrated to 300 mL. Hexanes crystallized from the mixture: mp 92-94 C.; 1 H NMR (d6 -DMSO) 7.8 (m, 2H), 7.3 (t, J=8.7Hz, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5760068; (1998); A;,
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Reference of 38336-04-8, 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(2-benzyloxyethyl)-2,6-dichloro-3-nitrobenzenesulfonamide Following the general procedure for sulfonamide formation outlined in example 15, 2,6-dichloro-3-nitrobenzenesulfonyl chloride (2.0 g, 6.88 mmol), 2-benzyloxyethyl amine(1.04 g, 6.88 mmol) and triethylamine(1.92mL, 13.76 mmol) were reacted to form the desired product (2.31 g, 83%). 1H NMR (MeOD-d4): delta 7.69 (d, 1H), 7.53 (d, 1H), 7.25 (m, 3H), 7.14 (d, 2H), 4.26 (s, 2H), 3.45 (t, 2H), 3.36 (t, 2H).

The synthetic route of 2-(Benzyloxy)-1-ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6500863; (2002); B1;,
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Application of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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 methyl 3-hydroxy-5-methoxybenzoate (Chakraporty, T. K. and Reddy, G. V. J. Org. Chem, 57, 1992, 5462.) (3.3 g, 18.1 mmol) in dry DMF (30 mL) was added K2CO3 (6.3 g, 45.3 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then ((2-bromoethoxy)methyl)benzene (3.4 mL, 21.7 mmol) was added and the mixture stirred at 160 C. for 2 hrs. The reaction was cooled down to room temperature and diluted with EtOAc, washed with water and brine, and dried over MgSO4, filtered and concentrated to give the crude product (90%) which was used in the next step without further purification.

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

Reference:
Patent; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6096-89-5, name is 2-(4-Fluorophenoxy)ethylamine, 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 6096-89-5, Application In Synthesis of 2-(4-Fluorophenoxy)ethylamine

Example 17: (Compound No. 223)Sodium salt of 3-[3-({3-[2-(4-fluorophenoxy)ethyl]-1 -propyl-2,4-dioxo-1 ,2,3,4- tetrahydroquinazolin-6-yl}carbonyl)imidazo[1 ,5-a]pyridin-1 -yl]benzoic acidMethyl 5-[(1 -bromoimidazo[1 ,5-a]pyridin-3-yl)carbonyl]-2-({[2-(4- fluorophenoxy)ethyl]carbamoyl}amino)benzoate4.75 g (16 mmol) of triphosgene are added, at ambient temperature under an inert atmosphere, to 4.99 g (13.33 mmol) of methyl 2-amino-5-({1 -[3- (methoxycarbonyl)phenyl]imidazo[1 ,5-a]pyridin-3-yl}carbonyl)benzoate in 220 ml of dioxane. After refluxing for 5 hours, 6.21 g (40 mmol) of 2-(4-fluorophenoxy)-1 – ethylamine and 4.05 g (40 mmol) of triethylamine are added at ambient temperature. The reaction medium is refluxed for 3 hours and then concentrated under reduced pressure. The residue is triturated from water. After filtration, the solid is rinsed with methanol and then dried under reduced pressure at 40C overnight. 6.67 g of a yellow solid are obtained.MH+: 555

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Fluorophenoxy)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; ALCOUFFE, Chantal; KIRSCH, Reinhard; HERBERT, Corentin; LASSALE, Gilbert; WO2012/4732; (2012); A1;,
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Related Products of 4393-09-3, 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. 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of EXAMPLE 7A (175 mg) in acetonitrile (4 mL) at 25 C. was treated with 2,3-dimethoxybenzylamine (85 mg) and N,N-diisopropylethylamine (450 muL), heated in a microwave reactor for 10 min at 50 C., and 20 min at 195 C., cooled, treated with tert-butyl (1S,4S)-(-)-2,5-diaza-bicyclo(2.2.1)heptane-2-carboxylate (119 mg), heated in a microwave reactor for 20 min at 195 C., cooled, treated with water, acidified to pH 3 with aqueous HCl, and extracted with ethyl acetate. The extract was washed with water, and concentrated. A solution of the concentrate in ethanol (4 mL) at 25 C. was treated with LiOH (0.1M, 5 mL), stirred for 18 hours, treated with water, acidified to pH 1 with aqueous HCl, and filtered.

The synthetic route of (2,3-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, David; Beutel, Bruce; Bosse, Todd D.; Clark, Richard; Cooper, Curt; Dandliker, Peter; David, Caroline; Gu, Yu-Gui; Hansen, Todd Matthew; Hinman, Mira; Kalvin, Douglas; Larson, Daniel P.; Lynch, Linda; Ma, Zhenkun; Motter, Christopher; Palazzo, Fabio; Rosenberg, Teresa; Rehm, Tamara; Sanders, William; Tufano, Michael; Wagner, Rolf; Weitzberg, Moshe; Yong, Hong; Zhang, Tianyuan; US2003/232818; (2003); A1;,
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171290-52-1, name is 3,5-Dimethoxyphenylacetylene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 171290-52-1

General procedure: A 10 mL reaction vial was charged with a terminal acetylenes 1a-p (1.0 mmol), piperidine (3.0 mmol), H2O (1 mL) and 30 mol% molecular iodine. The reaction vial was then heated at 100 C for 12 h. After completion of the reaction (progress was monitored by TLC; SiO2, Hexane/EtOAc = 9.5:0.5), the mixture was diluted with ethyl acetate (15 mL) and water (20 mL) and extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with brine (3 × 10 mL) and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the remaining residue was purified by column chromatography over silica gel using hexane / ethyl acetate (9.5:0.5) as an eluent to obtain the desired products 2a-p in high yields.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kaldhi, Dhananjaya; Vodnala, Nagaraju; Gujjarappa, Raghuram; Kabi, Arup K.; Nayak, Subhashree; Malakar, Chandi C.; Tetrahedron Letters; vol. 61; 16; (2020);,
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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, Safety of 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 heatedon a steam bath for 4 hr. The resulting 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%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethoxy)-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; John Wyeth & Brother Limited; US3992389; (1976); 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. 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H5BrF3NO

EXAMPLE 122 N-(4-Chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-8-(trifluoromethoxy)-3-quinolinecarboxamide [] A mixture of 4-bromo-2-trifluoromethoxyaniline (10.0 g) and diethyl ethoxymethylenemalonate (7.9 mL) is heated to 135 C for 2 h. The reaction mixture is diluted with diphenylether (90 mL) and heated to reflux with removal of ethanol by a Dean-Start trap for 30 min. The resulting precipitate is poured into heptane and filtered to afford 10.83 g (73%) of the 6-bromo-8-trifluoromethoxyquinoline ethyl ester. A mixture of the quinoline ethyl ester (5.0 g) and 4-chlorobenzylamine (12.0 mL) are heated to 190 C for 1 h. The mixture is diluted with toluene (25 mL), allowed to cool to rt, and filtered. The crude product is recrystallized (HOAc, water) to afford 5.03 g (80%) of the amide. The resulting amide (469 mg), bis(triphenylphosphine)palladium (II) chloride (175 mg), and triethylamine (5.0 mL) are dissolved in DMF (50 mL). Propargyl alcohol (2.5 mL) is added over 20 h at 90 C. The reaction mixture was allowed to cool to rt, poured into aq. ammonium chloride (200 mL) and extracted with ethyl acetate (4 x 50 mL). The organic layer is washed with sat. aqueous brine (10 mL). The aqueous layer is back-extracted with ethyl acetate (20 mL). The combined organic layers are dried (MgSO4) and concentrated. The crude product is purified by column chromatography (dichloromethane/ methanol, 100/1; 50/1; 100/3) to afford 580 mg (26%) of the title compound as a white solid. Physical characteristics are as follows: Mp 262 C dec.1H NMR (DMSO-d6) delta 12.89, 10.12, 8.64, 8.20, 7.86, 7.42-7.34, 5.42, 4.55, 4.35.13C NMR (CF3CO2D) delta 175.7, 167.4, 144.1, 139.1, 134.8, 133.3, 131.5, 129.2, 129.1, 127.3, 126.3, 123.6, 123.2, 120.6, 107.3, 84.8, 84.1, 55.5, 44.1.IR (drift) 1936 (w), 1657 (s), 1602, 1574, 1544, 1517 (s), 1279 (s), 1268, 1223 (s), 1212 (s), 1183, 1161 (s), 1048, 1020, 802 cm-1.MS (ESI-) m/z 449 (M-H)-.Anal. Found for C21H14ClF3N2O4: C, 55.86; H, 3.16; N, 6.09; Cl, 7.96

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 175278-09-8.

Reference:
Patent; Pharmacia & Upjohn Company LLC; EP1042295; (2005); B1;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Fluoro-2-methoxybenzene

A mixture of 2-fluoroanisole (1.78 mL, 15.9 mmol), cyclopropanecarbonitrile (4.68 mL, 63.6 mmol), and KHMDS (0.5 M solution in toluene, 50 mL, 24 mmol) was stirred and heated to 60 C. under N2. After 5 h, the mixture was allowed to cool to room temperature, then treated with 1 N HCl and extracted twice with toluene. The toluene extracts were combined, washed with brine, dried over Na2SO4, filtered, and the solvent was removed in vacuo. The oily residue was dissolved in CH2Cl2 and purified by chromatography on silica gel (gradient 3:1 hexanes/CH2Cl2 to CH2Cl2) to provide compound 6 (530 mg, 21%) as a clear, colorless oil: 1H NMR (300 MHz, CDCl3) delta 7.19-7.34 (m, 2H), 6.88-6.93 (m, 2H), 3.93 (s, 3H), 1.58-1.63 (m, 2H), 1.23-1.27 (m, 2H).

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; Termin, Andreas; Grootenhuis, Peter D.J.; Wilson, Dean M.; Molteni, Valentina; Mao, Long; Castellino, Angelo; Yang, Zhicai; Pechulis, Anthony; Suto, Mark; US2003/229091; (2003); A1;,
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