Tag: M.W=100-200

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. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., Recommanded Product: 2′-Methoxyphenyl acetylene

1-Ethynyl-2-methoxybenzene (2a, 265 mg, 2 mmol) and benzyl azide (266 mg, 2 mmol) were added to a 1 : 1 water-tert-butyl alcohol mixture (8 mL). A freshly prepared 1 M aqueous solution of sodium ascorbate (200 muL, 0.2 mmol) and an aqueous solution of CuSO 4 ¡¤ 5 H 2 O (65 muL, 5 mg, 0.02 mmol) were then added in succession, and the mixture was stirred for ~14 h at room temperature (TLC). The mixture was diluted with 30 mL of ice water and kept for 15 min in an ice bath, and the white precipitate was filtered off, thoroughly rinsed with cold water (2 ¡Á 15 mL), and dried under reduced pressure. Yield 474 mg (89%), off-white solid. 1 H NMR spectrum, delta, ppm: 8.11 s (1H), 7.58 d (2H, J = 7.4 Hz), 7.42 t (1H, J = 8.5 Hz), 7.34-7.28 m (3H), 7.16 d (1H, J = 7.1 Hz), 7.00-6.94 m (2H), 6.13 s (2H), 3.70 s (3H). 13 C NMR spectrum, delta C , ppm: 159.5, 139.5, 136.7, 131.6, 129.2, 128.5, 128.1, 126.5, 120.3, 109.2, 104.1, 56.1, 54.0. Mass spectrum: m/z 266.1214 [M + H] + . Calculated for C 16 H 16 N 3 O: 266.1217.

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jabeen; Khera; Iqbal; Asgher; Russian Journal of Organic Chemistry; vol. 55; 9; (2019); p. 1416 – 1422; Zh. Org. Khim.;,
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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 50592-87-5 as follows. category: ethers-buliding-blocks

In an appropriate vessel for microwave was mixed 1-bromo-6-methoxyhexane (183 mg ; 0.94 mmol ; 1eq) and tributylphosphine (209 mg (95% pure : 220 mg) ; 1.03 mmol ; 1.1 eq) under inert atmosphere (glove box). Then the mixture was irradiated under microwave (200W) at 130C for 2 hours. The obtained viscous mixture was washed, triturated and centrifuged twice with Et2O, then the supernatant was removed and the obtained residue was taken up into DCM and dried over high vacuum. It led to a pale yellow oil (338 mg ; 0.85 mmol ; 90%). 1H-NMR (CDCl3, 400MHz): delta 3.36 (t, 2H, J 6.4 Hz), 3.31 (s, 3H), 2.41 (m, 8H), 1.47-1.61 (br, 18H), 1.41 (quint, 2H, J 7.2), 0.96 (t, 9H, J 6.6 Hz). 13C-NMR (101 MHz ; CDCl3): delta 72.5, 58.7, 30.7, 29.3, 25.7, 24.1, 22, 19.5, 19, 13.6 ; 9 signals obscured or overlapping. 31P-NMR (162 MHz ; CDCl3): delta 33.78. ESI MS : 317.3 m/z : M+ ; 713.5 m/z : [Br-M+]M+. Elemental analysis: calc % (C19H42BrOP 1/3 CH2Cl2): C, 53.24 ; H, 9.85. Found %: C, 52.94 ; H, 10.22.

According to the analysis of related databases, 50592-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brunel, Frederic; Lautard, Christelle; Garzino, Frederic; Giorgio, Suzanne; Raimundo, Jean M.; Bolla, Jean M.; Camplo, Michel; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3770 – 3773;,
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Application of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

28.a. 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (This product is obtained according to Sugasawa T; Toyoda T; Adachi M; Sasakura K, J. Am. Chem. Soc., 100 (1978), p.4842-4852). Boron trichloride (1M in heptane, 156 ml, 156 mmol) is added dropwise, under an argon atmosphere at 0¡ã C. to a solution of 3-fluoro-4-methoxy-aniline (20 g, 142 mmol) in anhydrous dichloromethane (200 ml). The pink suspension thus obtained is maintained under agitation for 5 minutes, then propionitrile (33 ml, 420 mmol) is added dropwise followed by aluminium trichloride (20.8 g, 156 mmol) in small portions. The reaction medium is heated under reflux for 3 hours, cooled down to 0¡ã C., hydrolyzed by cautiously adding 2N hydrochloric acid (100 ml), then heated at reflux for 45 minutes. After cooling down to 0¡ã C. a precipitate is obtained which is filtered out, washed with dichloromethane, then taken up in water (300 ml). The aqueous phase is basified to an alkaline pH, extracted with dichloromethane then ethyl acetate. The organic phase is dried (MgSO4) then evaporated to produce a crude product which is purified by column chromatography (SiO2, AcOEt/Hpt: 1/99 to 20/80). 15.3 g of a yellow solid is obtained. NMR-1H (CDCl3): 1.20 (t, 3H); 2.92 (q, 2H); 3.83 (s, 3H); 6.2 (s, 2H); 6.40 (d, 2H); 7.32 (d, 2H). IR (KBr): 857; 1148; 1240; 1561; 1583; 1662.

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Societe de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6815546; (2004); B2;,
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Synthetic Route of 20781-20-8, These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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.

Step 1: synthesis of methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate (86) A mixture of 2,4-dimethoxybenzylamine (58.7 mmol, 8.81 ml, 9.81 g), methyl 5-chloro-4-nitrothiophene-2-carboxylate (45.1 mmol, 10 g) and potassium carbonate (180 mmol, 24.94 g) were stirred at rt in Acetonitrile (226 mL) for 1 h. Reaction was quenched with water and the resulting precipitate was collected to give methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate 86 (15.5 g, 97%). NMR (400 MHz, CDCl3) 3.82 (s, 3H), 3.85 (s, 3H), 3.86 (s, 3H), 4.45 (d, J=5.9 Hz, 2H), 6.46 (dd, J=8.2 Hz and 2.3 Hz, 1H), 6.50 (d, J=2.3 Hz, 1H), 7.20 (d, J=8.2 Hz, 1H), 7.99 (s, 1H), 8.89 (br s, 1). (m/z)=353 (M+H)+.

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Folmer, Brigitte Johanna Bernita; Man, de Adrianus Petrus Antonius; Gernette, Elisabeth Sophia; Corte Real Goncalves Azevedo, Rita; Ibrahim, Hemen; US2013/79341; (2013); A1;,
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Synthetic Route of 20265-97-8, A common heterocyclic compound, 20265-97-8, name is 4-Methoxyaniline hydrochloride, molecular formula is C7H10ClNO, 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 solution of 2-oxazolidinone (1.5 g, 17.2 mmol) in 2-(2-ethoxyethoxy)ethanol (20 mL) was treated with p-anisidine hydrochloride (2.1 g, 17.2 mmol) and heated in the microwave at 150 C. at 300 W for 10 min. The solution was cooled to rt and Et2O (50 mL) was added. The resulting solid precipitate was filtered and washed with Et2O (3¡Á20 mL). HPLC: Rt=0.23. MS (ESI): mass calcd. for C9H14N2O, 166.1; m/z found, 150 [M-16]+.

The synthetic route of 20265-97-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allen, Darin; Choong, Ingrid; Lew, Willard; US2008/207683; (2008); A1;,
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These common heterocyclic compound, 767-91-9, name is 2′-Methoxyphenyl acetylene, 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. Recommanded Product: 2′-Methoxyphenyl acetylene

General procedure: A mixture of aryl iodide (2 mmol), aryl alkyne (2.4 mmol), Ni(OAc) 2 (10 mol %), Et3N (6 mmol) and 1,4-dioxane (15 mL) were charged into the reactor (steel bomb). The reactor was closed and pressurized to ~2bar CO and then stirred at 100 C for 4 h. The reaction Progress was monitored by TLC. The reaction mixture was cooled to room temperature, before being filtered through a pad of Celite. The filtrate was concentrated and purified by silica gel with a mixture of hexane and ethyl acetate to give the pure product. For all examples, reactions were performed on 100 mg scale of corresponding aryl iodides.

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

Reference:
Article; Charugandla, Renuka; Vangala, Markandeya Sarma; Chidara, Sridhar; Korupolu, Raghu Babu; Tetrahedron Letters; vol. 59; 34; (2018); p. 3283 – 3287;,
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Electric Literature of 1836-62-0, These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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.

Example 1 : Preparation of carvedilol phosphate 4-(Oxiranylmethoxy)-9H-carbazole (75 gm) was added to 2-(2- methoxyphenoxy)ethylamine (140 gm) at room temperature, followed by stirring the reaction mixture for 37 hours at room temperature. Ethyl acetate (385 ml) was added to the reaction mass, followed by maintaining the resulting mass at room temperature for 1 hour 30 minutes. The resulting mass was cooled to 0 to 5C and then maintained at the same temperature for 1 hour 30 minutes. The separated solid was filtered, washed with chilled ethyl acetate and then dried to obtain carvedilol. To the carvedilol obtained was added acetone (300 ml) and water (100 ml) at room temperature. To the reaction mixture was added phosphoric acid (5 ml), followed by stirring the reaction mixture at room temperature. The separated solid was filtered and then dried to obtain 90 gm of carvedilol phosphate.

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; MURALIDHARA REDDY, Dasari; SUBASH CHANDER REDDY, Kesireddy; VAMSI KRISHNA, Bandi; WO2014/108921; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 2734-70-5, name is 2,6-Dimethoxyaniline, 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 2734-70-5, Application In Synthesis of 2,6-Dimethoxyaniline

[0729j N-(2,6-dimethoxyphenyl)-6-methylnicotinamide, Example 370.1. To a stirred solution of 6-methylnicotinic acid (3.1 g, 22.8 mmol) and TEA (9.5 mL, 68.5 mmol) in DMF (76 mL) was added HATU (9.6 g, 25.1 mmol). After 3 mi 2,6- dimethoxyaniline (3.5 g, 22.9 mmol) was added. The resulting mixture was stirred at RT until LCMS analysis indicated that the reaction was complete. The reaction mixture was quenched using a mixture of saturated aqueous sodium bicarbonate and brine, then was extracted with EtOAc (4X). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 25-100percent EtOAc/hexanes) to provide 370.1 (4.2 g, 68percent yield) as atan solid. LCMS-ESI (POS), mlz: 273.2 (M+H).

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; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (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. 634-36-6, name is 1,2,3-Trimethoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H12O3

General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.

The synthetic route of 634-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Methoxy-5-(trifluoromethyl)aniline

EXAMPLE 22 3-{4-[3-(2-Methoxy-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide 82.4 mg (0.278 mmol) of triphosgene, followed by 0.223 cm3 of triethylamine, are added, at a temperature in the region of 20 C., under an argon atmosphere, to 0.2 g (0.793 mmol) of 3-(4-aminophenyl)-1H-pyrrolo-[3,2-b]pyridine-2-carboxamide in solution in 18 cm3 of tetrahydrofuran. After stirring for 1 hour at a temperature in the region of 20 C., 182 mg (0.952 mmol) of 2-methoxy-5-trifluoromethylphenylamine in solution in 17 cm3 of tetrahydrofuran are added. After stirring for 16 hours at a temperature in the region of 20 C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give a residue which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile] (90/5/5 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 109 mg of 3-{4-[3-(2-methoxy-5-trifluoromethylphenyl)ureido]-phenyl}-1H-pyrrolo[3,2-b]pyridine-2-carboxamide are obtained in the form of a yellow solid that melts at around 194 C.; 1H NMR (300 MHz, (CD3)2SO d6, -delta in ppm): 3.99 (s: 3H); 6.97 (broad s: 1H); from 7.18 to 7.27 (m: 2H); 7.33 (dd, J=9 and 1 Hz: 1H); 7.56 (d, J=9 Hz: 2H); 7.63 (d, J=9 Hz: 2H); 7.66 (very broad s: 1H); 7.81 (dd, J=8 and 1.5 Hz: 1H); 8.40 (dd, J=4.5 and 1.5 Hz: 1H); 8.58 (m: 2H); 9.56 (s: 1H); 11.88 (very broad s: 1H). MS-ES+: m/z=470(+)=(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; AVENTIS PHARMA S.A.; US2007/259910; (2007); A1;,
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