Category: ethers-buliding-blocks

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. 7664-66-6, name is 4-Isopropoxyaniline, A new synthetic method of this compound is introduced below., Product Details of 7664-66-6

To a solution of 4-isopropoxyaniline (9.06 g, 60.0 mmol) in CH2Cl2 (120 mL) and pyridine (30 mL) was added 4-nitrophenyl chloroformate (10.9 g, 54.0 mmol) portionwise with stirring over 1 min with brief ice-bath cooling. After stirring at room temperature for 1 h, the homogeneous solution was diluted with CH2Cl2 (300 mL) and washed with 0.6 M HCl (1*750 mL) and 0.025 M HCl (1*1 L). The organic layer was dried (Na2SO4) and concentrated to give the title compound as a light violet-white solid (16.64 g, 98%). 1H NMR (CDCl3) delta 8.31-8.25 (m, 2H), 7.42-7.32 (m, 4H), 7.25-7.20 (m, 2H), 6.93 (br s, 1H), 2.90 (sep, J=6.9 Hz, 1H), 1.24 (d, J=6.9 Hz, 6H). LC/MS (ESI) calcd for C16H17N2O5 (MH)+ 317.1, found 633.2 (2 MH)+.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281755; (2006); A1;,
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Electric Literature of 1579-40-4, 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. 1579-40-4 name is Di-p-tolyl Ether, 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.

Tolyl ether (10 g, 0.05 mol), benzoic acid (7.5 g, 0.06 mol), zinc chloride (20 g, 0.15 mol) and phosphorus oxychloride (15 ml, 0.16 mol) were heated at 95C for two hours. The mixture was cooled to room temperature and ethyl acetate (25 ml) was added to form a suspension. The suspension was poured into 500 ml stirring DI water at room temperature. The mixture was heated under reflux for 15 minutes and cooled down to room temperature overnight. The mixture was filtered and washed with water (100ml). The damp cake was suspended with 300 ml of methanol and stirred to boil for 2 or 3 minutes. The resultant suspension was allowed to cool to room temperature over a period of 3 hrs and was then filtered, washed with methanol and dried to give the title compound as a solid (14 g, 91. 8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Di-p-tolyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; ISIS PHARMACEUTICALS, INC.; WO2005/77966; (2005); 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. 109-85-3, name is 2-Methoxyethylamine, A new synthetic method of this compound is introduced below., Product Details of 109-85-3

Example 8: BenzvI-{l-f2-(lH-indoI-4-ylV4-morpholin-4-vI-thieno[3,2- dl py rimidine-6-y Imethyll -piperidin-4-yl) -(2-methoxy-ethyl)-amine; l-BOC-4-piperidone (2.00 g) and 2-methoxyethylamine (872 mul) were stirred together in methanol (20 ml) at room temperature for 12 hours. Sodium borohydride (760 mg) was added in several aliquots over 30 minutes and the reaction mixture stirred for a further 12 hours at ambient temperature. The solvents were removed in vacuo and the residue diluted with dichloromethane (50 ml) and washed with brine, dried (MgSO4). The solvents were removed in vacuo to give a residue which was purified by flash silica chromatography to give 4-(2-methoxy-ethylamino)-piperidine- 1-carboxylic acid tert-butyl ester (1.69 g) as a colourless oil.

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; PIRAMED LIMITED; WO2007/122410; (2007); A1;,
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Application of 801282-00-8, The chemical industry reduces the impact on the environment during synthesis 801282-00-8, name is 2-Fluoro-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

2,2-dimethyl-l ,3-dioxane-4,6,-dione (4.58 g, 31.78mmol) in trimethyl orthoformate (27.3mL, 245.9 mmol) was refiuxed at 100 C for 1 hr. 2-fluoro-3-methoxyaniline (3.9 g, 27.63 mmol) was then added and refluxing was continued for an additional hour. The reaction was cooled to room temperature and the suspension was filtered. The solid was washed with MeOH (60 mL) and dried under vacuum to yield the title compound. XH NMR H20438-004-04 (400MHz, chloroform-d) delta= 1 1.36 – 1 1.38 (m, 1H), 8.63-8.60 (m, 1H), 7.26- 6.83 (m, 3H), 3.92 (s, 3H), 1.75 (s, 6H).

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, 2-Fluoro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CALDWELL, John, P.; CAPLEN, Mary Ann; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LANKIN, Claire; LI, Derun; LIU, Hong; MCCRACKEN, Amy; MCKITTRICK, Brian; RAO, Ashwin; TAGAT, Jayaram, R.; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; ZHANG, Tianyuan; (132 pag.)WO2018/34917; (2018); 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. 111-95-5, name is Bis(2-methoxyethyl)amine, A new synthetic method of this compound is introduced below., Computed Properties of C6H15NO2

Example 391: N-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]bis(2-methoxyethyl)amine After the [6-[(4-chlorophenylsulfonyl)(2, 5-difluorophenyl)methyl]pyridin-3-yl]carbaldehyde (100 mg, 0.245 mmol) obtained in Example 335, bis(2-methoxyethyl)amine (70 mg, 0.53 mmol) and acetic acid (0.029 ml, 0.51 mmol) were dissolved in 1,2-dichloroethane (5 ml), sodium triacetoxyborohydride (115 mg, 0.515 mmol) was added to the resulting solution at room temperature.. The resulting mixture was stirred at room temperature for 3 days.. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixture.. The mixture was separated and the organic layer thus obtained was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous magnesium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash silica gel chromatography and a fraction obtained from the elution portion with hexane:ethyl acetate = 3:2 was concentrated under reduced pressure to yield a white solid.. The solid was washed with hexane, whereby the title compound (101 mg, 0.192 mmol, 78%) was obtained as a white powder.1H-NMR (400 MHz, CDCl3) delta: 2.73 (4H, t, J = 5.8 Hz), 3.31 (6H, s), 3.47 (4H, d, J = 5.8 Hz), 3.75 (2H, s), 5.93 (1H, s), 6.88-6.97 (1H, m), 6.97-7.07 (1H, m), 7.38 (2H, d, J = 8.8 Hz), 7.50-7.60 (3H, m), 7.76 (1H, dd, J = 8.1, 2.0 Hz), 7.98-8.08 (1H, m), 8.54 (1H, d, J = 2.0 Hz). MS m/z: 525 (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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 707-07-3, name is (Trimethoxymethyl)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 707-07-3, Application In Synthesis of (Trimethoxymethyl)benzene

To a solution containing diol 2 (7.1 g, 49.6 mmol) and trimethyl orthobenzoate (15 ml, 87.3 mmol) in chloroform (150 ml), was added camphor sulphonic acid (500 mg), and the reaction mixture was concentrated to 1/3 of its original volume using a rotavap; TLC revealed that the reaction is not finished, so more chloroform (-100 ml) was added to the mixture, and the solution was concentrated to its 1/3 volume again. This cycle was repeated until TLC indicates the complete consumption of starting material (usually 3-4 cycle needed). Et3N (1 ml) was added to the reaction mixture and the solvent was removed completely; the resulting syrup was treated with a 20% [ACOH-H20] solution (140 ml). After 30 min, the reaction was concentrated to dryness. The syrupy mixture was purified by column chromatography on silica gel using 5% AcOEt-toluene to afford 20 (6.17 g, 50%) and 21 (5.47 g, 44. [6%).’H] NMR (CDCl3, 600 MHz) for 20: [88.] 03 (m, 2H, Bz), 7.55 (m, [1H,] Bz), 7.43 (m, 2H, Bz), 5.94 (ddd, 1H, [J6.] 4,10. 6,17. 0 Hz, H-4), 5.41 (ddd, 1H, J 1.3, 1.3, 17.2 Hz, [H-5_TRANS),] 5.31 (ddd, 1H, J 1.3, 1.3, 10.4 Hz, H-5_cis), 4.57 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J 7.] 7,11. 7 Hz, H-lb), 4.28 (m, 1H, H-3), 3.80 (ddd, 1H, J 3.5, 5.3, 7.7 Hz, [H-2). H] NMR (CDC13,600 MHz) for 21: [88.] 05 (m, 2H, Bz), 7.57 (m, 1H, Bz), 7.44 (m, 2H, Bz), 5.97 (ddd, [1H,] J 7.0, 10.6, 17.4 Hz, H-4), 5.66 (m, 1H, H-3), 5.48 (ddd, 1H, J 1.1, 1.1, 17.2 Hz, H- 5trans), 5.31 (ddd, [1H,] [J0.] 9,0. 9,10. 6 Hz, H-5_cis), 3. 83 (ddd, 1H, [J4.] 4,7. 1,9. 2 Hz, H-2), 3. 78 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J7.] 7,11. 7 Hz, H-lb),

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:
Patent; BUNDLE, David, R.; LING, Chang, Chun; ZHANG, Ping; WO2003/101937; (2003); A1;,
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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 886762-08-9 as follows. category: ethers-buliding-blocks

Into a 250-mL 3-necked round-bottom flask, was placed 5-bromo-2- (trifluoromethoxy) aniline (2 g, 7.81 mmol, 1 equiv), ethanol (20 mL), HCl (2 mL). This was followed by the addition of NaN02 (595 mg, 8.62 mmol, 1.10 equiv) dropwise with stirring at 0 C. To this was added water (110 mL), sulfuric acid (5.5 mL). The resulting solution was stirred for 1.5 h at 0 C in a water/ice bath. The resulting solution was allowed to react, with stirring, for an additional 12 h while the temperature was maintained at 100 C in an oil bath. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of sodium bicarbonate. The mixture was dried over anhydrous sodium sulfate. This resulted in 1 g (50%) of the title compound as an oil. Analytical Data: LC-MS: (ES, m/z): RT =1.715min, LCMS 53: m/z = 257 [M+l].

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
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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. 6358-77-6, name is 5-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6358-77-6

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 1000 mg; 5.37 mmol; 1.0 eq.) and formic acid( 1.22 ml32.25 mmol; 6.0 eq.). RM is cooled down to 0 C and sodium formate ( 73.11 mg; 1.07 mmol; 0.2 eq.) is added in this temperature. RM is stirred at room temperature for 2 h. After this time RM is diluted with DCM and sodium formate is filtered off. Filtrate is washed, with water and saturated aqueous solution of NaHC03.0rganic solvent is dried over anhydrous Na2S04 overnight. After this organic solvent is evaporated to afford N-(5-bromo-2-methylphenyl)formamide ( 869.50 mg; yield 68.8 %; 91.0 % by UPLC) as a brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); 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. 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Step C Preparation of 2-[3-(3-Methoxy-phenyl)-propyl]-malonic acid diethyl ester Diethylmalonate (7.65 mL, 0.050 mol) was added slowly to a vigorously stirred suspension of pre-washed NaH (60%) (2.4 g, 0.050 mol) in dry DMF (50 mL) at 0 C. under Ar. After 15 min, 3-(3-methoxyphenyl)propylbromide (11.5 g, 0.050 mol) was added slowly, the ice bath was removed, and the reaction mixture was stirred at 65 C. for 16 hr. The mixture was cooled, partitioned between EtOAc (250 mL) and H2O (200 mL), the organic layer washed with H2O (2*500 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound. FAB MS(M+1) 309.1

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; deSolms, S. Jane; Stokker, Gerald E.; Shaw, Anthony W.; US2002/99007; (2002); 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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Methoxy-4-(methoxymethyl)benzene

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), the ketone (1.0 mmol), 2,6-lutidine (164 mL, 151 mg, 1.40 mmol) and TMSOTf (271 muL, 333 mg, 1.50mmol). The mixture was cooled to 0 Cand p-methoxybenzyl methyl ether (167mL, 167 mg, 1.10 mmol) was added. The reaction mixture was allowed to warmslowly to ambient temperature and stirred for 16 h, then it was passed througha column of silica (2 cm x 1 cm) with Et2O. The solvent was removedin vacuo and the residue was purified by column chromatography (0-5%EtOAc/hexanes).

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; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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