Tag: M.W=100-200

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 1515-95-3 as follows. HPLC of Formula: C9H12O

General procedure: In a 25 ml dry round-bottom flask was suspended polymeric PhIO (0.25 equivalent) indry acetonitrile at 23C. Then, Al(NO 3 ) 3 (0.35 equivalent) was added and stirred for10 min, afterward, it was cooled to 0C. The benzylic aryl derivative (1 equivalent) wasincorporated in one portion. The reaction was warmed to 23C for a period of 2-4 huntil the starting material was fully consumed judging its advance by TLC. The reactionmixture was quenched by the addition of NH 4 Cl saturated solution (25 mL) and thenextracted with EtOAc (3 10 mL). The organic extracts were collected, dried overanhydrous sodium sulfate, filtered, and concentrated in vacuo to remove the solventand yield the crude of the reaction. The product was purified by flash column chroma-tography on silica gel (100-200 mesh) with EtOAc/hexane system.

According to the analysis of related databases, 1515-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yahuaca-Juarez, Berencie; Gonzalez, Gerardo; Ramirez-Morales, Marco A.; Alba-Betancourt, Calara; Deveze-Alvarez, Martha A.; Mendoza-Macias, Claudia L.; Ortiz-Alvarado, Rafael; Juarez-Ornelas, Kevin A.; Solorio-Alvarado, Cesar R.; Maruoka, Keiji; Synthetic Communications; vol. 50; 4; (2020); p. 539 – 548;,
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Related Products of 80936-82-9, 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. 80936-82-9, name is 4-(Methoxymethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

The synthetic route of 4-(Methoxymethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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10541-78-3, name is 2-Methoxy-N-methylaniline, 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: C8H11NO

General procedure: To a stirred solution of amine derivative (3 .0 mmol ) in 10 mL of anhydrous py ridine under ice cooling, was addeda solution of 2 chlorosulfonyl benzoic acid 3.6 mmol ) in dichloroethane 10 mL) dropwise. The reaction mixturewas stirred at room temper ature under the nitrogen atmosphere for overnight. After completion of the reactio n(monitored by TLC), reaction mixture was diluted with chloroform (20 mL) and quenched with water (10 mL),extracted with chloroform (3x 3 0 mL), the organic layer was washed with 1N HCl (50 mL), then with water (50mL) The combined organic layers were dri ed over Na 2 SO 4 and evaporated in vacuo . The crude compoundrecrystallized from ethanol to afford the desired product 1a m

The synthetic route of 10541-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junmin; Wang, Qiuhong; Li, Xiangkang; Zhao, Yongli; Arkivoc; vol. 2019; 6; (2019);,
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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. 801282-00-8, name is 2-Fluoro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Safety of 2-Fluoro-3-methoxyaniline

Preparation of compound 10[00177] To a solution of compound 9 (13 g, 92 mmol) in DMF (100 mL) was added a solution of NBS (16.4 g, 92 mmol, 1.0 eq) in DMF (100 mL) drop-wise. The reaction mixture was stirred at room temperature for 3h, then diluted with ethyl acetate (500 mL) and washed with brine (2xl50mL). The organic phase was dried (Na2S04), filtered and concentrated to give the title compound (10) as brown oil (23 g, 98%) yield). ESI-MS (M+H)+: 219.9.

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; TONG, Youzhi; WO2011/29392; (2011); A1;,
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Electric Literature of 1535-75-7,Some common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, molecular formula is C7H6F3NO, 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: General Procedure A: To a pressure tube containing ethyl 4,4,4- trifluoroacetoacetate (1.2 eq) and Eaton”s reagent [7.5% wt. phosphorous pentoxide p- toluenesulfonic acid solution ( 1 mL/0.3 mmol)], was added the corresponding aniline (1 eq). Then the pressure vessel was sealed and heated to 130 , and the reaction mixture was stirred overnight. After cooling to 0 C, the reaction was poured into ice water (~5 mL/1 mmol) and the solution pH was adjusted to 5 by the addition of saturated aqueous potassium carbonate. In situations when a pale yellow precipitate was formed, the solution was filtered and the residue was washed with water and cold ethanol, then dried in vacuo to yield the crude 4-hydroxyquinoline. Alternatively, the solution could be extracted with CHCl3 (20 mL x 3) and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo to give the crude 4-hydroxyquinoline. Then the residue was purified by column chromatography using hexane”EtOAc as an eluent (30% of EtOAc) to give the desired products with yields ranging from 45% to 60%. (0217) Characterization data for compound 1 and 1a e have been reported by Kozikowski. [0140] 8-trifluoromethoxy-2-trifluoromethyl-4-quinolinol (compound 1): Yield 51%.1H NMR (DMSO-d6) 7.19 (1H, s), 7.74 (1H, apparent t, J = 8.4 Hz), 7.88 (1H, d, J = 7.2 Hz), 8.28 (1H, d, J = 8.4 Hz), 9.71 (1H, br s).13C NMR (DMSO-d6) 101.5 (q, J = 2.4 Hz), 119.9, 120.8 (q, J = 258 Hz), 122.4 (q, J = 273 Hz), 123.5, 123.7, 127.3, 128.8, 141.8 (q, 1.8 Hz), 144.5 (q, J = 36 Hz), 163.9. UVmax: 294 nm, 303 nm, 315 nm

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

Reference:
Patent; THE TRUSTEES OF DARTMOUTH COLLEGE; CHEUNG, Ambrose Lin Yau; NAIR-SCHAEF, Dhanalakshmi R.; WU, Jimmy; CHEN, Ji; (73 pag.)WO2017/136642; (2017); 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 171290-52-1

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in the compound 7d (85.3 mg, 300 mumol),1-ethynyl -3,5-dimethoxy-benzene (121 mg, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. The reaction mixture was stirred at 40 for 47 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) to yield a compound 2d as a brown solid using (98.8mg, 74%) .

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 171290-52-1.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Application of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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.

b) 2-Methyl-2-{[1-(2-phenoxy-ethylamino)-naphthalene-2-carbonyl]-amino}-propionic acid3 mg copper(l)iodide, 127 mg potassium phosphate and 105 mg 2-[(1-bromo- naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester were placed in a reaction vial, which was evaporated and backfilled with argon three times. A solution of 62 mg 2-phenoxyethylamine and 12 mg N,N-diethylsalicylaminde in 0.5 ml of dry DMF was then added via septum. Under inert conditions the reaction mixture was heated to 1000C for 20 h. It was then diluted with ethyl acetate and water, the pH was adjusted to neutral, the layers were separated and the aqueous layer was extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate and evaporated. After purification by RP-HPLC 12 mg 2-methyl-2-{[1-(2-phenoxy- ethylamino)-naphthalene-2-carbonyl]-amino}-propionic acid were obtained.C23H24N2O4 (392.46), LCMS (ESI): 393.16 (MH+).

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

Reference:
Patent; SANOFI-AVENTIS; WO2008/409; (2008); A1;,
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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.

Example 163N-(2,2-diethoxyethyl)-5-{4-[4-({[(2-fluoro-5- methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrole-3-carboxamideA mixture of 5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxylic acid (500mg, 1.12mmol), HATU (467mg, 1.23mmol) and N,N- diisopropylethylamine (322mg, 2.5mmol) in anhydrous DMF (10ml) was stirred at room temperature for 10 minutes, followed by addition of aminoacetaldehyde diethyl acetal (194mg, 1.46mmol). The mixture was stirred for another 10 minutes and poured into 100ml of water. The precipitates were filtered, washed with water and dried in vacuo to give N-(2,2- diethoxyethyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2- yl}-1H-pyrrole-3-carboxamide as white solid. Yield: 580mg, 92%. 1H NMR (DMSO-d6): 11.83 (br. s., 1H), 9.18 (s, 1H), 8.49 (d, J = 2.9 Hz, 1H), 8.38 (d, J = 5.6 Hz, 1H), 7.99 (dd, J = 7.9, 2.3 Hz, 1H), 7.94 (t, J = 6.0 Hz, 1H), 7.54 – 7.60 (m, 2H), 7.40 (dd, J = 3.1, 1.6 Hz, 1H), 7.10 – 7.19 (m, 4H), 7.08 (t, J = 2.2 Hz, 1H), 6.78 – 6.84 (m, 1H), 6.71 (dd, J = 5.6, 2.3 Hz, 1H), 4.56 (t, J = 5.6 Hz, 1H), 3.62 (dq, J = 9.7, 7.0 Hz, 2H), 3.47 (dq, J = 9.7, 7.0 Hz, 2H), 3.24 (t, J = 5.7 Hz, 2H), 2.28 (s, 3H), 1.11 (t, J = 7.0 Hz, 6H) LR MS (ES+): 562 (MH+) LR MS (ES-): 560 (M-H)

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

Reference:
Patent; ALLERGAN, INC.; GUO, Xialing; ZHU, Zhen; WO2015/69287; (2015); A1;,
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Electric Literature of 458-52-6, These common heterocyclic compound, 458-52-6, name is 2-Fluoro-4-methoxyaniline, 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 C 2-Fluoro-4-methoxyphenyl isocyanate A solution of 8.8 grams (0.062 mole) of 2-fluoro-4-methoxyaniline in 70 mL of toluene was stirred, and a solution of 12.3 grams (0.062 mole) of trichloromethyl chloroformate in 30 mL of toluene was added dropwise. Upon completion of addition, the reaction mixture was warmed to reflux, where it was stirred for about 18 hours. After this time the reaction mixture was cooled and concentrated under reduced pressure, yielding about 10.4 grams of 2-fluoro-4-methoxyphenyl isocyanate. The product was used immediately in the next reaction.

The synthetic route of 458-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5399543; (1995); A;,
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Electric Literature of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3). 4.1.11.1. trans-N-(2-Phenoxyethyl)-3-phenyl-1,4-dioxane-2-carboxamide (26a). This compound was prepared starting from 24a and 2-phenoxyethanamine: a solid was obtained (73% yield;mp 109-110 C). 1H NMR (CDCl3) d 3.56 (m, 2H), 3.84e4.01 (m, 6H),4.08 (d, 1H, J 9.0 Hz), 4.42 (d, 1H, J 9.0 Hz), 6.60 (br t, 1H,exchangeable with D2O), 6.86e7.38 (m, 10H). ESI/MS: m/z 328.2[M H]. Anal. Calcd for C19H21NO4: C, 69.71%; H, 6.47%; N, 4.28%.Found: C, 69.87%; H, 6.23%; N, 4.39%.

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

Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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