Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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 102-52-3, Computed Properties of C7H16O4

1. The starting precursor 2-bromomalonaldehydewas prepared using procedure given in literature [S. Trofimenko, J.Org. Chem. 28(11) (1963), 3243-3245.], [W.J. Tomsho, J.J. McGuire, K. Coward, Org. Biomol. Chem. 3(18) (2005)3388-3398.].To a 100 ml of aqueous solution of 1,1,3,3-tetramethoxypropane (1) (100g, 0.12 M) added concentrated HCl (4.3 ml) and stirred untilit forms homogeneous solution, the temperature of the reaction mixturemaintained was below 35 0C,then slowly added bromine (0.15 M) solution drop wise.After the completeaddition of bromine, stirring was continued for another 30 minutes. Then thereaction mixture was concentrated under vacuum, maintaining the temperature below50 0C until thick slurry was obtained. The obtained slurry waswashed with 200 ml cold water and 100 ml of cold dichloromethane and dried invacuum. Yield: 65%, MP: 148 0C (Lit: 146-147 0C [W.J. Tomsho, J.J. McGuire, K. Coward, Org. Biomol. Chem. 3(18) (2005)3388-3398.],148 0C [M.J. Grard, Compt. Rend. Acad. Sciences. 190 (1930)187:Ann.1930, 13, 336.].

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; Yallur, Basappa Chanabasappa; Katrahalli, Umesha; Krishna, Panchangam Murali; Hadagali, Manjunatha Devagondahalli; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 222; (2019);,
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Related Products of 1836-62-0, 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.

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-(2-Methoxyphenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Synthetic Route of 707-07-3, 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. 707-07-3 name is (Trimethoxymethyl)benzene, 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.

Method 2; Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in xylene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for 4 h. The mixture is cooled down to 0 0C and the mother liquor is separated. The solid is subsequently washed with xylene (14 ml) and a mixture of xylene (8 ml) and ethyl acetate (8 ml). After drying 14,3 g (81 ,0 %) of the “chlorenol” compound are isolated as yellow crystals.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71523; (2009); A1;,
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1484-26-0, name is 3-Benzyloxyaniline, 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. HPLC of Formula: C13H13NO

4-Chloro-6-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7Hpyrrolo-[2,3-d]pyrimidine [8] (600 mg, 1.46 mmol) and 3-(benzyloxy)aniline (585 mg, 2.94 mmol) were dissolved in nbutanol(12 mL) under an N2-atmosphere. The reaction mixturewas agitated at 100 °C for 6.5 hours. Following work-up asdescribed in Section 2.4.1, the crude product was purified twiceby silica-gel column chromatography (n-pentane/THF, 9/2, Rf = 0.37). Drying gave 661 mg(1.15 mmol, 79percent) of a orange solid.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reiers°lmoen, Ann Christin; Han, Jin; Sundby, Eirik; Hoff, Bard Helge; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 562 – 578;,
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Reference of 5111-65-9, 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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows.

SYNTHESIS EXAMPLE 1; According to a reaction path of Reaction Scheme 1, compound 19 represented by Formula 19 was synthesized: Synthesis of Compound 19; Synthesis of Intermediate A; 7.5 g (32 mmol) of 2-bromo-6-methoxynaphthalene, 4.6 g (25 mmol) of phenoxazine, 3.7 g (38 mmol) of sodium tert-butoxide ((t-BuO)Na), 0.3 g (0.33 mmol) of Pd2(dba)3 [(tris(dibenzylidine acetone) dipalladium (0))], and 0.11 g (0.55 mmol) of tri(tert-butyl)phosphine were dissolved in 125 mL of toluene and were reacted for 12 hours at 80 C.After the reaction was completed, the reaction mixture was cooled down to an ambient temperature and 200 ml of distilled water was added and quenched. Then, xylene and water were extracted in the volume ratio of 1:1.The collected organic layer was dried and concentrated using MgSO4 and a column chromatography was performed using an eluant formed of toluene and hexane in the volume ratio of 1:2. The obtained effluent was concentrated and dried to obtain 6.8 g (Yield: 80%) of intermediate A. The structure of intermediate A was identified through 1H NMR spectroscopy.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-methoxynaphthalene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Son, Jhun-Mo; Yu, Eun-Sun; Kwon, O-Hyun; Son, Young-Mok; Kim, Yu-Jin; US2007/176541; (2007); A1;,
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Related Products of 332-48-9, A common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

b) 2-({4-Bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2- methyl-propionic acid methyl esterTo 90 mg cesium carbonate and 92 mg 2-[(4-bromo-1-hydroxy-naphthalene-2- carbonyl)-amino]-2-methyl-propionic acid methyl ester in 1 ml abs. DMF 60 mg 4- fluorophenoxyethylbromide was added. After 16 h at room temperature the reaction was poured unto ice-water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. After purification by RP-HPLC 61 mg of 2-({4-Bromo-1-[2-(4- fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester were obtained. _ _ _ . . _ – – c24H23BrFNO5 (504.36), LCMS (ESI): 504.05, 506.05 (MH+, bromo-pattern).

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; SANOFI-AVENTIS; WO2008/409; (2008); A1;,
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Application of 82830-49-7,Some common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, molecular formula is C8H9FO2, 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 an oven-dried round-bottom flask with a stir bar were charged with a solution of secondary amines 2 (1.5 mmol) in 1 mLdry THF at room temperature under an argon atmosphere. To thissolution was slowly added 1.2 mL nBuLi (2.5 mol/L in n-hexane,3.0 mmol) via syringe. After stirring at 25 C for 10 min, a solution of fluoroarene 1 (1.0 mmol) in 1mL dry THF was added to the reaction flask. The reaction mixture was stirred for 0.5 h at 25 C, and then quenched with 2 mL saturated aqueous solution of NaCl and extracted with H2O (20 mL) and ethyl acetate (3 20 mL). The organic layer was separated and dried with anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude product was purified by column chromatography on silica gel using a petroleum ether/ethyl acetate mixture as eluent to afford the pure target compounds.

The synthetic route of 82830-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Yingyin; Li, Meng; Ji, Xinfei; Wu, Jingjing; Cao, Song; Tetrahedron; vol. 73; 11; (2017); p. 1466 – 1472;,
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Synthetic Route of 80936-82-9,Some common heterocyclic compound, 80936-82-9, name is 4-(Methoxymethyl)aniline, molecular formula is C8H11NO, 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.

5.3b (1.1 g, 8.02 mmol, 1.0 equiv) was dissolved in acetone: water (2:1, 9 mL) and cooled toO C. NaHCO3 (1.42 g, 16.86 mmol, 2.1 equiv) and CBZ-Cl (1.78 g, 10.44 mmol, 1.3 equiv) were added and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a residue. The residue was purified by silica gel column chromatography (2-5 % EtOAc in Hexane) to afford product 5.3c (1.56 g, 72 % yield). 1H NMR (400 MHz, DMSO) 6 9.80 (s, 1H), 7.49-7.38 (m, 6H), 7.23 (t, J= 6.5 Hz, 2H), 5.15 (s, 2H), 4.32 (s, 2H), 3.25 (s, 3H).

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

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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 54149-17-6, HPLC of Formula: C5H11BrO2

Example 83 Preparation of 17-[2-(2-methoxyethoxy)ethyl]-N-(pyridin-3-yl)morphinan-3-amine (83), hydrochloride salt Step 1 : Preparation of 17-[2-(2-etaiotabeta1iotaomicronchigamma61iotaomicronchinu)61iotagamma1]etaiotaomicronphi1iotaeta3eta-3-gamma1 trifluoromethanesulfonate, The acetonitrile solution of morphinan-3-yl trifluoromethanesulfonate (2.7 g, 7.19 mmol), l-bromo-2-(2-methoxyethoxy)ethane (2.6 g, 14.4 mmol) and cesium carbonate (2.6 g, 43.2 mmol) was heated at 50 C for 18 hours. After cooling the mixture to room temperature, all solvent was removed and the reaction mixture was extracted with dichloromethane twice. The solvent was evaporated and the residue was purified by silica gel chromatography using Biotage with dichloromethane/methanol eluents. 17-[2-(2- Methoxyethoxy)ethyl]morphinan-3-yl trifluoromethanesulfonate was obtained as a light- yellow liquid (2.5 g, 73% yield), MS (EI) for C22H30F3NO5S: 478.2 (MH+).

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; NEKTAR THERAPEUTICS; ANAND, Neel; AURRECOECHEA, Natalia; CHENG, Lin; DENG, Bo-liang; O’MAHONY, Donogh; MU, Yongqi; KROGH-JESPERSEN, Erik; (215 pag.)WO2016/182840; (2016); A1;,
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