Tag: M.W=100-200

Synthetic Route of 74654-07-2, A common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, molecular formula is C7H17NO3, 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.

General procedure: A solution of compound (ZDR019) (3.0 g, 7.88 mmol), dimethylamine hydrochloride (1.92 g, 23.6 mmol), sodium triacetoxyborohydride (3.32 g, 15.7 mmol) and N,N- diisopropylethylamine (4.8 ml_, 27.5 mmol) in 1,2-dichloroethane (150 mL) was stirred at room temperature for 18 h. The reaction was quenched through the addition of water (100 mL) and the pH adjusted to pH 6-7 using aqueous phosphate buffer solution (0.5 M, pH 7) . The mixture was then diluted with dichloromethane (100 mL) and the separated aqueous layer further extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with aqueous phosphate buffer solution (0.5 M, pH 7) (100 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash chromatography (dichloromethane/methanol, 20: 1 10: 1 7: 1) afforded compound (ZDR022) as a white solid (2.40 g, 5.86 mmol, 74%).

The synthetic route of 74654-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTAGO INNOVATION LIMITED; BRIMBLE, Margaret Anne; COOK, Greg Murray; FERGUSON, Scott Andrew; HEIKAL, Adam; RENNISON, David; (130 pag.)WO2019/125185; (2019); 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., SDS of cas: 1836-62-0

Example -4: Preparation of carvedilol In a dry reaction flask charged 25.0 g 4 – (2,3-epoxy propoxy) carbazole (0.104 moles), 39.35 g of 2 – (2- methoxy phenoxy) ethylamine (0.235moles) in 250 ml dimethyl sulfoxide. The temperature of the reaction mass was raised to about 70C under stirring and maintaining the reaction mixture at 68 – 72C for 18 – 20 hrs. The reaction mass was cooled to about 30C and quenched the reaction mass in 250 ml water, stirred and extracted the resultant solution in 250 ml dichloromethane. The organic layer was separated and washed with aqueous sulphuric acid till pH of the washings about 7.0 – 8.0. The organic layer was separated and further adjusted the pH with the aqueous sulfuric acid to 4.0 – 4.5 to precipitate carvedilol sulphate salt. The precipitated salt was filtered and taken in 300 ml ethyl acetate and made alkaline with 10% sodium carbonate solution. The reaction mass was stirred and separated the organic layer. The ethyl acetate was distilled under vacuum, and 330 ml toluene was added to it. The solid obtained was filtered and crystallized from ethyl acetate to obtain pure carvedilol. Yield = 58 – 62%.

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; IPCA Laboratories Limited; EP1741700; (2007); A1;,
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Reference of 710-18-9, A common heterocyclic compound, 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, molecular formula is C8H7F3O2, 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.

Under N2 atmosphere, an oven-dried 4 mL vial was charged with l-methoxy-4- (trifluoromethoxy)benzene (57.6 mg, 45.5 mu, 0.300 mmol, 1.00 equiv), palladium complex 1 (11.4 mg, 15.0 muetaiotaomicron, 5.00 mol ), Ag(bipy)2C104 (16.0 mg, 30.0 muetaiotaomicron, 10.0 mol ), and NFBS (0.189 g, 0.600 mmol, 2.00 equiv). Acetonitrile (0.75 mL, c = 0.40 M) was added and the reaction mixture was stirred in a sealed vial at 23 C for 24 h. Subsequently, triethylamine (30.5 mg, 42.0 mu, 0.300 mmol, 1.00 equiv) was added and the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with hexanes/EtOAc (19: 1 to 4: 1 (v/v) with 1% triethylamine), to afford 89.2 mg of the title compound as a colorless solid (61 yield). [00215] Rf = 0.30 (hexanes/EtOAc 4: 1 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDC13, 23 C, delta): 7.97 (d, J = 7.6 Hz, 4H), .65-1.69 (m, 2H), 7.54 (t, J = 7.6 Hz, 4H), 7.29 (dd, J = 9.5, 2.9 Hz, 1H), 6.95 (d, J = 2.9 Hz, 1H), 6.85 (d, J = 8.6 Hz, 1H), 3.43 (s, 3H). 13C NMR (125 MHz, CDC13, 23 C, delta): 156.8, 141.8, 139.8, 134.0, 128.9, 128.9, 126.5, 125.1, 123.4, 120.6 (q, J = 255 Hz), 112.4, 55.8. 19F NMR (375 MHz, CDC13, 23 C, delta): -59.9. Mass Spectrometry: HRMS (ESI-TOF) (m/z): calcd for C20H2oF3N206S2 [M + NH4]+, 505.0709, found, 505.0721.

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; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; NGAI, Ming-Yu; BOURSALIAN, Gregory, Bagrad; MCNEILL, Eric, Andrew; RITTER, Tobias; WO2015/31725; (2015); A1;,
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Synthetic Route of 910251-11-5, The chemical industry reduces the impact on the environment during synthesis 910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, I believe this compound will play a more active role in future production and life.

4-Fluoro-2-(4-fluorophenyl)-5-isopropoxy-6-(methoxymethyl)-N- methylbenzofuran-3-carboxamide A mixture of 6-bromo-4-fluoro-2-(4-fluorophenyl)-5-isopropoxy-N- methylbenzofuran-3-carboxamide (600 mg, 1.414 mmol) , potassium methoxymethyltrifluoroborate (2149 mg, 14.14 mmol), PdCl2(dppf) (310 mg, 0.424 mmol) and cesium carbonate (2074 mg, 6.36 mmol) in a mixture of toluene (60 mL) and water (20 ml) was flushed with N2 and then stirred at 85C for 48 hrs. The mixture was diluted wih EtOAc (200 mL). The water layer was removed. The organic layer was filtered and then concentrated to give a crude solid, which was purified by column chromatography (Biotage 25m, EtOAc/Hexane = 0 to 30%) to give 280 mg (51 %) of the product as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.99 – 7.92 (m, 2H), 7.41 (s, 1H), 7.21 – 7.13 (m, 2H), 6.12 (br. s., 1H), 4.62 (d, J=0.5 Hz, 2H), 4.56 – 4.47 (m, 1H), 3.51 – 3.47 (m, 3H), 3.07 (d, J=5.0 Hz, 3H), 1.37 (m, 6H). LCMS R, = 3.151 min., m/z 390 (M + H). The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Phenomenex Luna 3muiotaeta C18, 2 x 50 mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoro acetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute.

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, Potassium trifluoro(methoxymethyl)borate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; EASTMAN, Kyle J.; PARCELLA, Kyle E.; WO2014/159559; (2014); A1;,
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Electric Literature of 645-36-3, 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. 645-36-3 name is 2,2-Diethoxyethanamine, 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.

First, 1-naphtaldehyde (1.6 g, 10 mmol) and 2,2-dietoxyethanamine (1.3 g, 10 mmol) were mixed, and the mixture was stirred at 100C for from 30 min to 1 h. After allowed to cool, the reaction mixture was mixed with EtOH (25 mL), and the resulting mixture was stirred and made homogeneous. Next, a small amount of NaBH4 (0.38 g, 10 mmol) was gradually added and the mixture was then stirred at room temperature for from 1 h to overnight. After completion of the reaction, EtOH was distilled away while the mixture was concentrated under reduced pressure. (An appropriate amount of) Water was added to the resulting residue, and a product was extracted with AcOEt. A separated organic layer was washed with saturated saline and dried with Na2SO4. After that, the sample was filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (AcOEt/hexane = 5/1) to yield compound 1 (2.3 g, 8.5 mmol, 85%) as colorless transparent liquid.

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

Reference:
Patent; National University Corporation Tottori University; KanonCure, Inc.; SHIOTA, Goshi; ITABA, Noriko; KANKI, Keita; SETO, Kenzo; SHIMIZU, Hiroki; KOUNO, Yohei; KUNITA, Shinya; ADUMI, Zyunya; SAKABE, Tomohiko; ABE, Kenichiro; MORIMOTO, Minoru; OKA, Hiroyuki; (77 pag.)EP3150207; (2019); B1;,
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Application of 1535-75-7, These common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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.

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

Statistics shows that 2-(Trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 1535-75-7.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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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. 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 6443-69-2

3,4,5-Trimethoxytoluene (1.82 g, 10 mmol) was dissolvedin a mixture of acetic acid (10 mL) and catalytic H2SO4 (0.01 mL), then a solution of the oxidant (15 mmol) was added dropwise over 10 min. The mixture was stirred and heated at 50C for 1 h. After cooling, the reaction mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic phases were washed with H2O and NaHCO3, then dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EtOAc, 5:1) to give CoQ0. CoQ0, red-colored needles, m.p. 55C-58C (Lit.1357C-59C).1H NMR (400 MHz, CDCl3): delta = 6.44 (q, J = 1.7 Hz, 1H),4.02 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 2.04 (d, J = 1.6 Hz,3H, CH3).13C NMR (101 MHz, CDCl3): delta = 184.4 (C=O), 184.2(C=O), 145.0, 144.8, 144.0, 131.2, 61.2 (OCH3), 61.1(OCH3), 15.4 (CH3).MS (ESI): m/z = 205 [M + Na]+.The spectroscopic data are in accord with the literature.

The synthetic route of 6443-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Bin; Qiu, Yong-Fu; Qi, Shi; Wang, Jin; Journal of Chemical Research; vol. 43; 11-12; (2019); p. 553 – 556;,
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Synthetic Route of 33170-72-8, 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. 33170-72-8 name is 2-Bromo-1,1-dimethoxypropane, 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.

A solution of methyl 5-amino-6-bromopyrazine-2-carboxylate (500 mg, 2.15 mmol, 1.00 equiv), 2-bromo-1,1-dimethoxypropane (1.2 g, 6.56 mmol, 3.00 equiv), p-toluenesulfonic acid (76 mg, 0.44 mmol, 0.20 equiv) in acetonitrile (20 mL) was stirred for 12 h at 80 C. The mixture was concentrated under vacuum and the residue was purified by a silica gel column eluting with dichloromethane/methanol (10:1). This resulted in 400 mg (69%) of the title compound as a yellow solid. LC-MS (ES, m/z): 270 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,1-dimethoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Blaquiere, Nicole; Castanedo, Georgette; Feng, Jianwen A.; Hu, Baihua; Staben, Steven; Yuen, Po-wai; Wu, Guosheng; Lin, Xingyu; Burch, Jason; US2015/57260; (2015); A1;,
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Reference of 24599-58-4, The chemical industry reduces the impact on the environment during synthesis 24599-58-4, name is 2,5-Dimethoxytoluene, I believe this compound will play a more active role in future production and life.

General procedure: Standard reaction conditions: a 1.0 mmol sample of the aryl ether was dissolved in 1.8mL of acetonitrile and was added slowly over several minutes to a rapidly stirred solution of CAN (1.92g, 3.5mmol) which had been dissolved in 1.8 mL of distilled water in a 10mL round-bottom flask. After the addition was complete, the mixture was stirred for an additional 1 hour at room temperature open to the air. The mixture was diluted with 25 mL of water, and the resulting precipitate collected by suction filtration. The precipitate was washed with several 10 mL portions of water and then finally with approximately 5mL of ice cold ethanol. The resulting yellow solid (diquinone) was dried at room temperature under vacuum.

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, 2,5-Dimethoxytoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Love, Brian E.; Simmons, Alexander L.; Tetrahedron Letters; vol. 57; 50; (2016); p. 5712 – 5715;,
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Application of 19500-02-8, These common heterocyclic compound, 19500-02-8, name is 3-Methoxy-2-methylaniline, 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.

A mixture of 1-methoxy-2-methyl-3-aminobenzene 15.0 g, triphosgene 48.7 g and toluene 350 mL was stirred withheating under ref lux for three hours. The reaction mixtures after standing to cool were condentrated under reduced pressure to give 1-methoxy-3-isocyanato-2- methylbenzene 17.0 g.?H NMR (CDC13) : 2.19(3H, S), 3.82(3H, 5), 6.69(1H, d, J=8.2Hz), 6.72(1H, dd, J=0.5, 8.0Hz), 7.09(1H, t, J=8.2Hz)

Statistics shows that 3-Methoxy-2-methylaniline is playing an increasingly important role. we look forward to future research findings about 19500-02-8.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; YOSHIMOTO, Yuya; TAKAHASHI, Teruki; OOHIRA, Daisuke; AZUMA, Shuhei; WO2013/162077; (2013); A1;,
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