Ethers-buliding-blocks

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 1484-26-0 as follows. 1484-26-0

A mixtureof triethyl orthoformate (92 mL, 0.55 mol) and 2,2-dimethyl- [1, 3] – dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at55 C for 90 minutes and then cooled to45 C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period 45 minutes while maintaining the reaction temperature below50 C. The reaction was then heated at45 C for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1 C, and the product was isolated by filtration and washed with cold ethanol (-400 mL) until the filtrate was colorless.5-{[(3- Benzyloxy) phenylimino]methyl}-2,2-dimethyl- [1, 3] -dioxane-4,6-dione (170.65 g) was isolated as a tan, powdery solid. ‘H NMR (300MHz, DMSO-d6) : 8 11.21 (d, J= 14.2 Hz, 1H), 8. 61 (d, J= 14.2 Hz, 1H), 7.49-7. 30 (m, 7H), 7.12 (dd, J= 8. 1,1. 96 Hz, 1H), 6.91 (dd, J= 8.4, 2.1 Hz, 1H), 5.16 (s, 2H), 1. 68 (s, 6H).

According to the analysis of related databases, 1484-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/48933; (2005); A2;,
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1535-73-5, 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. 1535-73-5 name is 3-Trifluoromethoxyaniline, 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 3-trifluoromethoxy aniline (0.5 g, 2.8 mmol) in CH2Cl2 (70 ml) is added dropwise, phenyl chloroformate (1.06 ml, 8.5 mmol) and pyridine (0.226 ml, 2.8 mmol) at 0 C. The reaction mixture is stirred at 0 C. for 30 min. The solution is washed with 0.1 N HCl, 5% NaHCO3, brine, and concentrated under vacuum. The resulting solid is crystallized from n-heptane to give white needles 0.6 g (71% yield). HRMS (EI) calcd for C14H10F3NO3 297.0613, found 297.0613. Example 405 (from 4-amino-3-methylphenol and phenyl 3-(trifluoromethoxy)phenylcarbamate) is prepared by following Method D, making non-critical modifications. The resulting residue is triturated with CH3CN to give an off white solid 0.07 g (33% yield). HRMS (ESI) calcd for C15H13N2O3F3+H 327.0956, found 327.0954.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Trifluoromethoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
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929-75-9, Adding a certain compound to certain chemical reactions, such as: 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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 929-75-9.

General procedure: A two-neck flask equipped with a magnetic stirrer and a reflux condenser was filled with dry argon and then charged with diazacrown ether 3 or 4 (0.2 mmol), Pd(dba)2 (8-16 mol.%), the phosphine ligand BINAP (9-18 mol.%), and anhydrous dioxane (10 mL). After stirring for 2-3 min, an appropriate amine 5 (0.2 mmol) and ButONa (0.6 mmol) were added. The reaction mixture was refluxed for 24 h. After completion of the reaction, the precipitate that formed was filtered off and washed with CH2Cl2 (10 mL). The combined filtrates were concentrated in vacuo. The residue was dissolved in CH2Cl2 (5 mL) and washed with water (3¡Á10 mL). The organic layer was separated, and the aqueous layers were combined to extract organic matter with CH2Cl2 (3¡Á10 mL). The combined organic fractions were dried over 4 A molecular sieves and concentrated in vacuo. The residual thick dark oil was chromatographed on silica gel using the following sequence of eluents: CH2Cl2, CH2Cl2-MeOH (100 : 1)-(3 : 1), CH2Cl2-MeOH-NH3 (100 : 20 : 1)-(10 : 4 : 1).

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, 1,11-Diamino-3,6,9-trioxaundecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chernichenko; Averin; Buryak; Beletskaya; Russian Chemical Bulletin; vol. 63; 9; (2014); p. 2056 – 2063; Izv. Akad. Nauk, Ser. Khim.; 9; (2014); p. 2056 – 2063,8;,
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These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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. 54314-84-0

Example 25; 5-{(lJ?)-2-[({l-[3-(Benzyloxy)propyl]-4-hydroxypiperidin-4-yl}methyl)amino]-l- hydroxyethyl}-8-hydroxyquinoin-2(lJH)-one; i) l-(3-Benzyloxy-propyl)-piperidin-4-oneA suspension of benzyl 3-bromo-propyl ether (2.29g), 4-piperidinone hydrate hydrochloride (1.69g), potassium carbonate (anhydrous) (3.45g) and potassium iodide (830mg) were stirred in dry DMF (40ml) at 85¡ãC and continued for 24 h. The reaction was poured into water (200 mL plus brine 25 mL) and extracted with EtOAc. The organic extract was evaporated and the residue was chromatographed on silica gel eluting with 4:3 EtOAc/isohexane giving the sub-titled compound as a colourless oil. Yield: 1.8g 1U NMR (300Mz, CDCl3) delta 7.39 – 7.32 (4H, m), 7.31 – 7.25 (IH, m), 4.52 (2H, d), 3.60 – 3.53 (2H, m), 2.79 – 2.70 (4H, m), 2.61 – 2.54 (2H, m), 2.48 – 2.41 (4H, m), 1.89 – 1.80 (2H, m)

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 54314-84-0.

Reference:
Patent; ASTRAZENECA AB; WO2007/102771; (2007); A1;,
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366-99-4, 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 366-99-4 as follows.

To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro-p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5 mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g, 97percent); mp 194¡ã C.; HPLC: Inertsil ODS 3V C18, 40:30:30 v:v:v [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 33.2 min, 97.6percent purity; MS (TOF ES+) m/z 396 (35.0); 394 (M+H, 100).

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
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768-70-7, 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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 ¡Á 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3.

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; Dhara, Kalyan; Kapat, Ajoy; Ghosh, Tridev; Dash, Jyotirmayee; Synthesis; vol. 48; 23; (2016); p. 4226 – 4268;,
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1579-40-4, Name is Di-p-tolyl Ether, 1579-40-4, 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.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

Statistics shows that Di-p-tolyl Ether is playing an increasingly important role. we look forward to future research findings about 1579-40-4.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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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 14869-41-1 as follows. 14869-41-1

2-Chlorethoxyacetic acid (1.11 g, 8 mmol) is dissolved in dichloromethane (22 mL), and thereto are added thionyl chloride (1.17 mL, 16 mmol) and dimethylformamide (30 muL, 0.4 mmol) successively at room temperature. After stirring at room temperature for 2.5 hours, the mixture is concentrated, and the residue is dissolved in dichloromethane (22 mL). To the mixture are added methyl 4-aminobenzoate (661 mg, 4 mmol) and pyridine (674 muL, 8 mmol) under ice-cooling, followed by stirring overnight. The reaction solution is washed with dilute hydrochloric acid, dried, and concentrated. The residue is subjected to silica gel column chromatography to give ethyl 4-(2-chloroethoxyacetylamino)benzoate (540 mg, 23.6percent).

According to the analysis of related databases, 14869-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1640373; (2006); 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. 22236-08-4, name is 3-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 22236-08-4

General procedure: A two neck round bottom flask under argon equipped with acondenser was charged with aldehyde 4 (1.0 equiv.) and 4-chloroaniline 3l (1.1 equiv.) in 2-pentanol [0.3 M] and stirred atreflux for 2 h. The tetronic acid 5 (1.1 equiv.) in 2-pentanol (minimumamount) was then added at reflux. After another 10 min atreflux, the third component aniline 3 (1.0 equiv.) was added neat.The reaction mixture was refluxed for an additional 30 min. Allvolatiles were evaporated under vacuum and the crude product purified by recrystallization in ethanol or by flash chromatographyon silica gel

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; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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402-07-3,Some common heterocyclic compound, 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, molecular formula is C8H6BrF3O, 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.

Synthesis of (2-(Hydroxy(2-methoxy-4-(trifluoromethyl)phenyl)methyl)- 1 ‘-tosyl-l – 1 ,3 ‘- bipyrrol-2’-yl)(2-methoxy-4-(trifluoromethyl)phenyl)methanone (37). To a solution of l-bromo-2-methoxy-4-(trifiuoromethyl)benzene (720 mg, 2.88 mmol) in dry THF (5 mL) at -78 C under N2 was slowly added n-BuLi (1.15 mL, 2.5 M in n-pentane, 2.88 mmol). After being stirred for 30 min, a solution of 36 (550 mg, 1.06 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4C1 (15 mL) solution and extracted with EtO Ac (10 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtO Ac/petroleum) to give 37 (400 mg, 54% yield) as a light yellow solid. 1H NMR (400 MHz, CDCI3) delta 2.44 (s, 3H), 3.59 (br s, 3H), 3.84 (s, 3H), 5.77 (br s, 1H), 6.17-6.32 (m, 3H), 6.49 (br s, 1H), 6.70 (br s, 1H), 6.83 (d, J= 7.6 Hz, 1H), 7.13 (br s, 1H), 7.21 (br s, 1H), 7.35-7.37 (m, 4H), 7.42 (d, J= 2.8 Hz, 1H), 7.92 (d, J= 8.0 Hz, 2H) ppm; 13C NMR (CDC13, 100 MHz) delta 21.67, 55.75, 55.88, 67.96, 105.60, 105.64, 108.13, 108.03, 111.28, 116.78, 116.78, 116.78, 120.85, 120.85, 124.97, 126.20, 127.10, 127.30, 127.63, 127.63, 129.14, 129.14, 129.98, 129.98, 132.50, 132.56, 133.21, 133.45, 135.92, 145.38, 155.48, 157.01, 180.50 ppm; IR (KBr) 3444, 3137, 2923, 1668, 1562, 1447, 1361, 1180, 1014, 752, 668 cm”1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-methoxybenzotrifluoride, its application will become more common.

Reference:
Patent; CHONGQING ZEIN PHARMACEUTICAL CO., LTD.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; QIN, Yong; CHENG, Chunwei; SONG, Hao; LI, Rongshi; LIU, Yan; WO2014/116634; (2014); A1;,
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