Tag: M.W=100-200

Application of 20469-61-8, A common heterocyclic compound, 20469-61-8, name is 1-Methoxy-2,3,5-trimethylbenzene, molecular formula is C10H14O, 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.

(2) Synthesis of 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride In 500 ml of methylene chloride was dissolved 4.5 g of 2,3,5-trimethylanisole and the solution was cooled to -5 C. to -10 C. A solution of 6.0 ml of chlorosulfonic acid in 400 ml of methylene chloride was added dropwise, and then the temperature was allowed to rise to room temperature. The mixture was poured into an ice–5% aqueous sodium hydrogen carbonate mixture. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off, and the residue was crystallized from n-hexane. Yield 5.0 g (67.0%). m.p. 56-58 C.

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; Takeda Chemical Industries, Ltd.; US4476051; (1984); A;,
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Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 suspension of the appropriate quinolonecarboxylic acid (1mmol) in 6mL of dry THF at 25C, HOBt (1.5mmol), WSC (1.5mmol) and the appropriate aminoalcohol (1.5mmol) were added sequentially. The mixture was stirred at room temperature under nitrogen, then the solvent was evaporated, water was added and the solid formed filtered. The crude product was purified by flash chromatography.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Beretta, Giangiacomo; Dallavalle, Sabrina; Tetrahedron; vol. 70; 52; (2014); p. 9797 – 9804;,
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Electric Literature of 24599-58-4, A common heterocyclic compound, 24599-58-4, name is 2,5-Dimethoxytoluene, molecular formula is C9H12O2, 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.

In a more recent development of the invention, work toward the synthesis of oosporein has progressed via several approaches. One set of approaches to the synthesis of oosporein utilizes 2,5-dimethoxytoluene (1) (commercially available, and available in one step in high yield from the very inexpensive starting material methylhydroquinone) as the initial starting material. Proper choice of oxidant and reaction conditions allowed preparation of either biphenyl derivative (2) or diquinone (3), both in high yield and good purity (Scheme 1).

The synthetic route of 24599-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PhytoMyco Research Corporation; US2007/110726; (2007); A1;,
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Application of 10541-78-3,Some common heterocyclic compound, 10541-78-3, name is 2-Methoxy-N-methylaniline, 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.

General procedure: Dichloromethane (20 mL) and phenylpropynoic acid (11 mmol) were added into a 50 mL round bottom glass flask, and then N-alkylaniline (10 mol) was added at 0 C. Thereafter, a solution of DCC (15 mol), DMAP (0.5 mmol) and dichloromethane (20 mL) was slowly added dropwise with stirring. The reaction mixture was allowed to warm to room temperature and then stirred overnight. The mixture was washed with 5 mL saturated NaCO3 solution, 5 mL saturated NaCl solution, and 5 mL water. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as the eluent) affording the corresponding N-phenylpropynamide 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-N-methylaniline, its application will become more common.

Reference:
Article; Chen, Yuan; Chen, Yu-Jue; Guan, Zhi; He, Yan-Hong; Tetrahedron; vol. 75; 51; (2019);,
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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 1579-40-4 as follows. Safety of Di-p-tolyl Ether

82 g (1.2 mol) of 50% hydrogen peroxide was slowly added into a mixture of 109 g (0.55 mol) of 4,4′-oxybis(methylbenzene) and 370 g (2.2 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). 4,4′-oxybis((bromomethyl)benzene) was obtained with a yield of 650% after removing the solvent from the crude product by evaporation.

According to the analysis of related databases, 1579-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ETERNAL MATERIALS CO., LTD.; HSUEH, Sheng-Yao; CHEN, Chih-An; LIN, You-Han; BAI, Hao-Tien; (19 pag.)US2017/36981; (2017); A1;,
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Some common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-methylaniline, 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. Recommanded Product: 2-Methoxy-4-methylaniline

General procedure: To a magnetically stirred ice-bath cooled solution of the selected succinic monoamide derivative (4 mmol) in anhydrous dioxane (20 ml) neat oxalyl chloride was added (8 mmol). After stirring over 30 min the reaction mixture was warmed to room temperature. Two hours later, the reaction mixture was re-cooled to 0 C in ice bath followed by drop wise addition of the particular aromatic amine (4 mmol) in pyridine (10 mL) to the reaction mixture. After stirring over 30 min the reaction mixture was warmed to room temperature and allowed to stir over 24 h. Subsequently, the reaction was carefully quenched with saturated sodium bicarbonate solution (200 mL). Finally, the mixture was filtered to offer the products as whitish to gray solids that were re-crystallized from acetone (see Scheme 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39538-68-6, its application will become more common.

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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7664-66-6, name is 4-Isopropoxyaniline, 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. Recommanded Product: 4-Isopropoxyaniline

Into a stirringmixture of ethyl acetate (20 mL), tetrahydrofuran (4 mL), water(4 mL), sodium carbonate (0.8 g, 7.9 mmol, 0.6 equiv.), and 4-isopropoxyaniline (2.0 g, 13.2 mmol, 1 equiv.), phenyl chloroformate(2.3 g, 14.5 mmol, 1.1 equiv.) was added dropwise at 0 C.The reaction was stirred at room temperature overnight, then itwas evaporated under reduced pressure and the resultant wasadded into 20 mL water, the precipitate was filtered and washedwith water, then dried under vacuum to afford 3.2 g of 13a as whitesolid; yield: 90%; MS (ESI) m/z: 286.1 [MH], 308.1 [MNa].

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

Reference:
Article; Li, Yingxiu; Ye, Tianyu; Xu, Le; Dong, Yuhong; Luo, Yong; Wang, Chu; Han, Yufei; Chen, Ke; Qin, Mingze; Liu, Yajing; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

3,3-diethoxypropan-1-amine (6 g, 40.76 mmol, 1.00 equiv) was dissolved in1,4-dioxane (30 mL) in the presence of TEA (4.45 g, 43.98 mmol, 1.08 equiv), then cooled to 0C. (Boc)20 (9.6 g, 43.99 mmol, 1.08 equiv) diluted in 20 mL of 1,4- dioxane was added drop-wise. The solution was agitated 2 hours at 0C then overnight at ambient temperature before being neutralised with 10 mL of water. The pH was adjusted to 5 with HC1 (1 %). The solution was extracted 3 times with 50 mL of EtOAc.The organic phases were combined, dried over sodium sulfate, filtered and concentrated to yield 8.21 g (81 %) of compound 1ZD in the form of a pale yellow oil.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174064; (2014); A1;,
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Synthetic Route of 1836-62-0,Some common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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.

A mixture of 9.7 g 4-(OXIRANE-2-YLMETHOXY)-9H-CARBAZOLE (II), 53.7 g of anhydrous hydrogen sulphate of 2-(2-METHOXYPHENOXY) ETHYLAMINE (III) and 28 g of anhydrous potassium carbonate in 200 ML ISOPROPANOL are, with intensive stirring, heated at 80 C for six hours. When the epoxide has reacted, the mixed salts are filtered off from the reaction mixture and isopropanol is distilled off from the filtrate. The obtained honey-like concentrate is diluted with heating in 50 ml of ethylacetate, the solution is cooled to the temperature of 40 C, it is inoculated and stirred at the temperature of 40 C for two hours. After the crystal precipitates, the mixture is cooled to the temperature of 0 C, and is kept like that with stirring for a minimum of four hours. After filtration and washing with cooled ethylacetate, 5.2 g of wet, crude Carvedilol is obtained (HPLC contents 95.2 area %, HPLC contents of the bis-derivative 2.8 area %).

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

Reference:
Patent; Zentiva, A.S.; WO2004/41783; (2004); A1;,
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Application of 160911-11-5, These common heterocyclic compound, 160911-11-5, name is 1-Fluoro-3-methoxy-5-methylbenzene, 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.

(40b) 1-Fluoro-5-methylphenol A solution of 1-fluoro-3-methoxy-5-methylbenzene obtained in Example (40a) (0.92 g, 6.56 mmol) and boron tribromide (1.0 M solution in methylene chloride, 8.53 mL, 8.53 mmol) in methylene chloride (20 mL) was stirred at 0C for 10 hours. Water (100 mL) was added to the reaction solution, followed by extraction with methylene chloride (100 mL). Then, the organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1) to obtain the title compound (0.83 g, yield: 99%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) delta: 2.06 (3H, s), 4.97 (1H, s), 6.37 (1H, dt, J = 2.4, 10.2 Hz), 6.44 (1H, s), 6.48 (1H, d, J = 8.6 Hz).

The synthetic route of 160911-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2138484; (2009); A1;,
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