Ethers-buliding-blocks

Some common heterocyclic compound, 109-85-3, name is 2-Methoxyethylamine, molecular formula is C3H9NO, 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. Computed Properties of C3H9NO

To an ice-cooled solution of 2-methoxyethylamine (623 mg, 8.29 mmol) and triethylamine (1.50 mL, 10.8 mmol) in anhydrous DCM (50 mL) under argon was added dropwise chloroacetyl chloride (795 muL, 10.0 mmol). After 4 h the mixture was flushed through a Strata SI-1 silica cartridge (20 g Giga Tube), eluting with DCM. Fractions containing the target material (Rf 0.65, 100% EtOAc) were combined and evaporated to afford 2-chloro-N-(2-methoxyethyl)acetamide (1.14 g, 7.50 mmol; 90%) as a brown oil: deltaEta (300 MHz, CDCI3): 6.92 (1 H, br s), 4.02 (2 H, s), 3.44-3.49 (4 H, m), 3.34 (3 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109-85-3, its application will become more common.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF GLASGOW; HERIOT-WATT UNIVERSITY; MOUNTFORD, Joanne; MILLIGAN, Graeme; ADAMS, Dave; (95 pag.)WO2016/92327; (2016); A1;,
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Electric Literature 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.

To a solution of alpha-bromo~2′-acetonaphthone (386.2 g, 1.57 mol) in dichloromethane (2.5 L) at 00C was added compound 3 (249.1 g, 1.65 mol) in 30 min, followed by the addition of triethylamine (220.7 mL, 1.57 mmol) in 45 min. After stirring at 00C for 40 min, the reaction mixture was warmed to room temperature and stirred overnight. The reaction solution was then washed with water (2x) and the aqueous layer was re-extracted with dichloromethane (2x). The combined organic extract was dried over sodium sulfate and concentrated in vacuo. The ketone, compound 4, was obtained as a reddish oil (513.3 g, quantitative), was used in the next step without further purification: ‘H NMR (CDCl3, 500 MHz) 8.50 (s, IH), 8.01(d, J= 8.5 Hz, IH), 7.92 (d, J = 8.0 Hz, IH), 7.88-7.85 (m, 2H)5 7.60-7.54 (m, 2H), 7.26-7.23 (m, IH), 6.97-6.94 (m, 2H), 6.82 (dd, J- 8.0, 2.5 Hz, IH), 3.88 (s, 2H), 3.75 (s, 3H), 3.69 (s, 2H), 2.42 (s, 3H); ESI MS m/z 320 [M+ H]+.

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; BRISTOL-MYERS SQUIBB COMPANY; ALBANY MOLECULAR RESEARCH, INC.; WO2009/149258; (2009); A2;,
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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. 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H13NO

To a solution of ethyl N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]sulfamoylacetate dihydrochloride (0.51 g) obtained in example 59(a) in ethanol (5 ml) were added successively 7-methoxy-3,4,5,6-tetrahydro-2H-azepine (0.34 g) and triethylamine (0.60 ml) at room temperature, and the resulting mixture was stirred at room temperature for 18 hours and then evaporated in vacuo.. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 25 % acetonitrile/water).. Subsequently, to a solution of the amorphous solid obtained in ethanol (5 ml) was added a 4N solution of hydrogen chloride in dioxane (1 ml), and the resulting mixture was evaporated to dryness in vacuo.. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.14 g, yield: 24 %) as a colorless amorphous solid. 1H NMR (400MHz, DMSO-d6) delta ppm: 1.23 (3H, t, J=7.0), 1.46-1.76 (8H, m), 2.01-2.10 (2H, m), 2.86-2.89 (2H, m), 3.45-3.50 (2H, m), 3.57-3.70 (2H, m), 3.85-3.97 (2H, m), 4.20 (2H, q, J=7.0), 4.34 (2H, s), 4.45 (2H, d, J=6.0), 4.70-4.76 (1H, m), 6.45 (1H, dt, J=16.0, 6.0), 6.55 (1H, d, J=16.0), 7.39 (2H, d, J=9.0), 7.54 (2H, d, J=9.0), 7.54 (1H, t, J=8.0Hz), 7.69-7.73 (2H, m), 7.90 (1H, s); IR (KBr, cm-1): 1737, 1674, 1629, 1351, 1158.

According to the analysis of related databases, 2525-16-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; EP1375482; (2004); 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Fluoro-2-methoxybenzene

Initially, 2-fluoroanisole (II) was used to synthesize 3-fluoro-4-methoxyacetophenone (III). AlCl3 (0.6 mol) and acetic anhydride (0.4 mol) were placed in 250 ml of dry dicloromethane. The 2-fluoroanisol (0.2 mol) was added dropwise over a period of 30 minutes to the reaction mixture which was then stirred with a magnetic stir bar for two hours. The reaction was judged complete by TLC. The reaction mixture was then poured in ice and stirred for one hour. The CH2 Cl2 layer was separated and the water layer was extracted twice with CH2 Cl2. Organic layers were combined and washed with 3N HCl and water, dried with MgSO4 and passed through a thick pad of silica. The solvent was rotary evaporated to obtain the crude product, which was crystallized from 7% (v/v) ethyl acetate in hexanes to obtain 70% yield of the crystallized product, 3-fluoro-4-methoxyacetophenone (III).

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; Displaytech, Inc.; US5422037; (1995); A;,
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Electric Literature of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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 a solution of substituted benzyl-1H-1,2,3-triazole-4-carboxylic acids (18a-e, 1 mmol) in dry dimethylformamide, EDCI (1.2 mmol) and HOBT (1.2 mmol) were added and the reaction mixture was stirred for 20 min. To the reaction mixture, amino Z-stilbenes (16, 17, 1 mmol) was added and stirred at room temperature for 12 h. The solvent was removed and the residue was dissolved in dichloromethane (50 mL), washed with 5% HCl (2 20 mL), 5% NaHCO3 (2 20 mL), and brine solution (20 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and the solvent was removed to give a crude product which was purified by chromatography (ethyl acetate/hexanes) to givethe desired product (6a-e, 7a-e).

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Bajee; Nayak, V. Lakshma; Nagaraju, Burri; Kapure, Jeevak Sopanrao; Shaheer Malik; Shaik, Thokhir Basha; Prasad; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5155 – 5167;,
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Reference of 5888-51-7, 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. 5888-51-7, name is 4-Ethyl-1,2-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A sealed tube equipped with a magnetic stirring bar was charged with ethylarene (1, 1.0 mmol), aq NH3 (2, 25% aq solution,10.0 mmol), I2 (1.1 mmol), and TBHP (6.0 mmol, 70% aq solution) at r.t. The resulting mixture was heated to 100 C for 3.0 h. After completion of the reaction (monitored by TLC), sat.Na2S2O3 solution (10 mL) was added to the reaction mixture,and it was extracted with EtOAc (2 ¡Á 20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on 100-200 mesh silica gel using EtOAc-n-hexane (1:2) as the eluent to obtain the corresponding benzamide 3.

The chemical industry reduces the impact on the environment during synthesis 4-Ethyl-1,2-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vadagaonkar, Kamlesh S.; Kalmode, Hanuman P.; Prakash, Sattey; Chaskar, Atul C.; Synlett; vol. 26; 12; (2015); p. 1677 – 1682;,
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Application of 1836-62-0, 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. 1836-62-0 name is 2-(2-Methoxyphenoxy)ethylamine, 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.

Step 2: Synthesis of 2-{4-[3-(2-methoxyphenoxyethylamino)propoxy]phenyl}3- (3,5-dimethoxyphenyl)acrylic acid methyl esterA suspension of 2-[4-(3-bromopropoxy)phenyl]-3-(3,5-dimethoxyphenyI) acrylic acid methyl ester (0.56 g, 1.3 mmol), 2-(2-methoxyphenoxy)ethylamine (0.23 mL, 1.5 mmol) and potassium carbonate (0.53 g, 3.8 mmol) in DMF (8 mL) was heated to 80 0C for 4 hours. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (2 x 100 mL). The ethyl acetate layer was washed with water (100 mL x 3), dried over anhydrous Na2SO4 and concentrated to afford the crude compound, which was purified by column chromatography using 2% methanol in dichloromethane as the eluent, to furnish the title compound (0.05 g, 7.5 % yield). 1H NMR (DMSO-d6) delta (ppm): 1.86-1.90 (2H, m, -CH2), 2.72-2.76 (2H, t, – CH2), 2.87-2.90 (2H, t, -CH2), 3.53 (6H, s, -OCH3), 3.70 (3H, s, -OCH3), 3.73 (3H, s, – OCH3), 3.99-4.02 (2H, t, -CH2), 4.04-4.07 (2H, t, -CH2), 6.27-6.28 (2H, d, Ar-H), 6.38- 6.39 (IH, m, Ar-H), 6.87-6.89 (2H, m, Ar-H), 6.94-6.97 (4H, m, Ar-H), 7.07-7.09 (2H, d, Ar-H), 7.67 (IH, s, =CH). MS m/z: 522.2 (M+l).

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

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED; WO2009/60282; (2009); A2;,
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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., Recommanded Product: 4-Methoxy-N-methylbenzylamine

A mixture of 3-(5-amino-2-chloro-4-fluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (2.5 g, 7.4 mmol) and 4-methoxy-N-methylbenzylamine (4 mL) was heated to 180¡ã C. under N2 for 3 h. After cooling, the reaction mixture was diluted with Et2O. The precipitate was filtered, washed with water, and dried to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 89percent yield). 1H NMR (400 MHz, DMSO-d6): delta 8.47 (s, 1H), 7.77 (s, 1H) 7.22 (m, 2H), 7.17 (d, J=8.0 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 5.86 (d, J=9.6 Hz, 1H), 6.30 (s, 1H), 5.32 (s, 2H) 4.87 (s, 1H), 3.72 (s, 3H), 3.52 (s, 3H), 3.09 (s, 3H); MS (ESI) m/z: 453.2[M+H]+.

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; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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Reference of 538-86-3,Some common heterocyclic compound, 538-86-3, name is (Methoxymethyl)benzene, molecular formula is C8H10O, 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: A sealed tube was charged with isochroman (or benzylic ether;1 mmol), DTBP (1.5 mmol), thiol (or thiophenol; 1.5 mmol). Thereaction mixture was stirred at 120 ¡ãC for 6 h. The reactionmixture was then cooled to obtain a brown liquid. The organicsolutions could be purified directly by column chromatographyon silica gel to give the pure product (hexane?EtOAc, 20:1).

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

Reference:
Article; Feng, Jie; Lu, Guoping; Lv, Meifang; Cai, Chun; Synlett; vol. 26; 7; (2015); p. 915 – 920;,
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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

General procedure: The starting hydrazide 4, 8e-i (10 mmol) was added to a mixture of the appropriate triethyl orthoester (10 mol) and 0.1 g p-TsOH in 20 mL of xylene and kept under reflux for 3 h (TLC). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane/AcOEt, 1:2 v/v) or crystallised from benzene/hexane mixture.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Ejsmont, Krzysztof; Tetrahedron; vol. 67; 40; (2011); p. 7838 – 7845;,
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