Month: July 2021

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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6F3NO

Stepl : 1-azido-2-(trifluoromethoxy)benzene (27a) Concentrated HCl (7.9 mL) was added to a solution of 2-(trifluoromethoxy)aniline (1.1 mL, 7.9 mmol) in EtOAc (26 mL) at 0 C. After 10min, a solution of sodium nitrite (1.6 g, 23.7 mmol) dissolved in water (4.6 mL) was added slowly over 5 min. The mixture was stirred for 30min, and then treated with a solution of sodium azide (1.5 g, 23.7 mmol) in water (5.3 mL) slowly over 5min. The reaction was stirred for 1 h then treated with phosphate buffer saline (pH 7.4, 50 mL). The mixture was extracted with EtOAc, the organics were washed with brine, dried over Na2S04 and concentrated to give compound 27a.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KROPF, Jeffrey, E.; SCHMITT, Aaron; WATKINS, William, J.; XU, Jianjun; GEGE, Christian; (92 pag.)WO2016/96116; (2016); A1;,
Ether – Wikipedia,
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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 768-70-7 as follows. category: ethers-buliding-blocks

Weigh 10 mg of the above catalyst, 0.5 mmol of compound 1, and 1 mmol of K3PO4 solids into a 10 ml Shrek tube.Seal the nozzle with a rubber stopper and protect it with vacuum argon.Using a microsampler, 1 mmol of Compound 2 and 5 ml of DMF solvent were injected into the reaction system through a rubber stopper.Place the reaction tube in an oil bath at 160 C.After 5h of reaction, the catalyst was filtered off,Obtain a uniform reaction solution, wash with water to remove DMF,Then, it is dried and separated by column chromatography to obtain 2- (3-methoxyphenyl) benzofuran of the following structural formula 5,NMR yield was 91%.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Tsingtao Biological Energies And Process Institute; Yang Yong; Ji Guijie; Duan Yanan; Zhang Shaochun; (10 pag.)CN110386909; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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 11 (Z)-3-((2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl)amino)-1-(3,4,5-trimethoxyphenyl) prop-2-en-1-one (10x) To a stirred solution of (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)aniline (5d) (100 mg, 0.317 mmol) in ethanol (5 ml) 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one (6x) (69.7 mg, 0.317 mmol) was added. The reaction mixture was stirred at a temperature of 30 C. for 4 h and the reaction was monitored by TLC using ethyl acetate/hexane (1:1) as a solvent system. Then water (10 ml) was added to reaction mixture. A yellow colour solid appears which was filtered and washed with ethanol. (yield: 120 mg, 70%); mp: 120-122 C.; 1H NMR (CDCl3, 500 MHz) delta (ppm): 12.09 (d, J=12.5 Hz, NH), 7.23-7.21 (m, 1H), 7.2 (s, 2H), 7.15 (d, J=1.8 Hz, 1H), 6.96 (dd, J=6.56 Hz, 1.8 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.54 (s, 2H), 6.49 (q, J=12.2 Hz, 2.44 Hz, 2H), 5.92 (d, J=7.9 Hz, 1H), 3.96 (s, 3H), 3.93 (s, 6H), 3.9 (s, 3H), 3.85 (s, 3H), 3.71 (s, 3H); FABMAS:(M+H)=536.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, its application will become more common.

Reference:
Patent; Council of Scientific and Industrial Research; Ahmed, Kamal; Gajjela, Bharath Kumar; Anver, Basha Shaik; Vangala, Santhosh Reddy; Mahesh, Rasala; US2015/322009; (2015); A1;,
Ether – Wikipedia,
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Electric Literature of 79128-08-8,Some common heterocyclic compound, 79128-08-8, name is 1,3-Diisopropoxybenzene, molecular formula is C12H18O2, 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.

at 0 adding n-butyllithium (2.5M, 40mL, 100mmol) in hexane solution was added to the compoundIt was 2 (19.4g, 100mmol) in THF (10 mL), and the mixture was stirred at 15 2 hours.After the mixture was cooled to 0 again, iodine (25.4g, 100mmol) were added thereto, and 10 The mixture was stirred for 16 hours. Saturated aqueous solution of sodium sulfite (50 mL) was added to the reaction solution toThe reaction was quenched, and the organic solvent was removed under reduced pressure. Thereafter, ethyl acetate (50mL × 3) extraction residue.The organic layer was dehydrated over sodium sulfate and concentrated. By using petroleum ether as eluent, concentrate purified by silica gel columnThereof, whereby the compound 3.

The synthetic route of 79128-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Polypropylene Corporation; Tanna, Akirahisashi; Sato, Naomasa; Konishi, Yohei; Oishi, Yasuo; (27 pag.)CN105593235; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 702-24-9, Formula: C9H13NO

N-methyl-4-methoxybenzylamine (30.2 mg, 0.2 mmol),Manganese chloride tetrahydrate (5.9 mg, 0.03 mmol),And a stirrer in the reaction tube,After replacing inert gas,Add 1 ml DMF,Seal the reaction tube.Place the reaction tube in a 150°C oil bath reaction pot.Stir the reaction for 10 hours;After cooling to room temperature,Diluted with 15mL water,And extracted three times with ethyl acetate,15mL each time;Combine the extracts,Dry with anhydrous sodium sulfate and filter.The filtrate was concentrated under reduced pressure.With ethyl acetate:The crude product was purified by column chromatography with petroleum ether = 1:2 (containing 1percent triethylamine) as eluent to give the pure product.Yellow oil,Yield 54percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-N-methylbenzylamine, and friends who are interested can also refer to it.

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Zhang Jingyu; (19 pag.)CN107986927; (2018); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

In a 250 mL round bottom flask was added 4-(diethylamino)thiobenzamide (2.29 g, 11 mmol) dissolved in ethanol (60 mL).Then 2-bromo-1,1-dimethoxyethane (1.86 g, 11 mmol) and p-toluenesulfonic acid (1.89 g, 11 mmol) were added and the reaction was heated to 95 C. overnight.After the reaction is completed, the mixture is cooled to room temperature, and the solvent is evaporated under reduced pressure. The crude product is purified by column chromatography (petroleum ether/ethyl acetate/triethylamine (V/V/V)=2/1/0.05).A white solid was obtained (1.40 g, 55%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,1-dimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, YINGJUN; ZHANG, JIANCUN; WANG, XIAOJUN; LIN, RUNFENG; CAO, SHENGTIAN; WANG, ZHAOHE; LI, JING; (226 pag.)TWI607995; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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. Quality Control of 4-(Difluoromethoxy)aniline

General procedure: Step-1:4-amino-2,6-dichloro pyrimidine: 2,4,6-trichloro pyrimidine (1.0 mmol) in ethanol (5 mL) was treated with an aromatic amine (1.1 mmol) in the presence of Na2CO3 (1.1 mmol) at rt. The mixture was stirred at reflux for 2-4 h until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, an equal volume of water was added with cooling. The resulting white precipitate was filtered, washed with water, and dried in vacuum over night to yield 4-substituted 2,6-dichloro pyrimidine. In case of no precipitation, ethanol was removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 4-amino-2,6-dichloro pyrimidines in 85-95% yield. Step-2: 2,4-diamino-6-chloropyrimidine: 4-amino-2,6-dichloro pyrimidine (1.0 mmol) prepared from the above procedure was treated with another aliphatic amine or aromatic amine (2.0 mmol) in the presence of DIEPA (5.0 mmol) in n-BuOH (5 mL) at rt. For an aliphatic amine the reaction mixture was stirred at rt for overnight. For an aromatic amine the reaction mixture was refluxed for 24-72 h or placed in microwave (150 C, 2-7 h) until completion of the reaction. The reaction progress was followed by TLC. After completion of the reaction, solvents were removed by rota vap., and the residue was dissolved in CH2Cl2. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography (EtOAc/hexane) to afford the 2,4-diammino-6-chloropyrimidines in 85-90% yield. Step-3: 2,4,6-triaminopyrimidine: 2,4-diamino-6-chloropyrimidine (1.0 mmol) prepared from the above procedure was treated with another suitable aliphatic amine or aromatic amine (3.0 mmol). For an aliphatic amine, 2,4-diamino-6-chloropyrimidine (1.0 mmol) was treated with aliphatic amine (3.0 mmol) and DIPEA (5.0 mmol) in n-BuOH (5 mL) and placed in microwave (150 C) for 3-7 h. After the completion of the reaction (monitored by TLC), solvents were removed and the residue was dissolved in EtOAc. The organic layer was washed twice with water, brine, dried (Na2SO4), filtered, and concentrated. The resulting crude was purified by column chromatography to afford the 2,4,6-triaminopyrimidines 90-95% yield. For aromatic amine; 2,4-diamino-6-chloropyrimidine (1.0 equiv) was dissolved in dioxane under argon and to that were added Pd2(dba)3 (10 mol %), Xantphos (10 mol %), aromatic amine (1.2 mmol), t-BuOK (1.2 mmol). The resulting solution was degassed with argon for 5 min and heated to 85 C for overnight. The reaction mixture was filtered through a pad of celite, washed with CH2Cl2 (2 × 10 mL) and the resulting filtrate was concentrated. The resulting crude was purified by flash column chromatography to yield 2,4,6-triaminopyrimidines in 90-95% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22236-10-8, its application will become more common.

Reference:
Article; Sagi, Vasudeva Naidu; Liu, Tianyu; Lu, Xiaoying; Bartfai, Tamas; Roberts, Edward; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7210 – 7215;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5, Computed Properties of C6H15NO2

Step E 3-[[Bis(2-methoxyethyl)amino]methyl]-2-(4-methoxyphenyl)-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide To a solution of the product of Step D (1.19 g, 3.68 mmol) and triethylamine (1.24 g, 12.3 mmol) in anhydrous THF (50 mL) was added methanesulfonic anhydride (1.07 g, 6.13 mmol). After 30 min, bis(2-methoxyethyl)amine (3 mL) was added and stirring continued for 18 h at ambient temperature. The reaction mixture was heated at reflux temperature for 1 h, cooled, poured into a saturated solution of sodium bicarbonate (100 mL) and this mixture was extracted with ethyl acetate (2*100 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate/hexane) to give a viscous oil (1.16 g, 72%).

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US5538966; (1996); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 6298-96-0,Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

The solid compound A (422 g) obtained in the above step was dissolved in 2.0 L of methanol and 10 L of a reaction flask was added.Lithium hydroxide (26 g) was weighed, dissolved in 2.0 L of pure water, and an aqueous solution of lithium hydroxide was added to the reaction flask. The temperature was controlled at 25-30 C for 1 hour, and the reaction was complete.Add water (4.0L) to the reaction flask, with 1N hydrochloric acid to adjust rhoH- = 2-3, a large number of solid precipitation, the solid material filter out, filter, with 2.9L dichloromethane solid solution Clear, magnetic stirrer slowly stirring.Weigh the s-p-methoxyphenylethylamine (151g), dissolved in 1.0L dichloromethane, the amine solution slowly added to the solution, dropping 40-50 minutes, the temperature control at 18 ~ 22 C, After the dropwise addition, the mixture was allowed to stand for 1 hour, and a large amount of fine granular solid and flocculent solid were precipitated. The granular solid sank into the bottom of the container and the floc floats on the upper part of the solution.After overnight, the supernatant was carefully poured out and the bottom solid was filtered and dried at 35 C under reduced pressure to give compound C, solid: 271 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Methoxyphenyl)ethylamine, its application will become more common.

Reference:
Patent; Shanghai Jinhe Bio-pharmaceutical Co., Ltd.; Zhang Weizhong; Wang Quanyong; Cai Zhixia; Xie Bin; Feng Leiyu; Wu Yujuan; Tong Zebin; (12 pag.)CN106632368; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 887581-09-1 as follows. category: ethers-buliding-blocks

Step 3: tert-butyl (2-bromo-5-methoxybenzyl)carbamate To a solution of 1-(2-bromo-5-methoxyphenyl)methanamine (3.2 mmol) in DCM (15 mL) was added BOC2O (3.2 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give tert-butyl (2-bromo-5-methoxybenzyl)carbamate (3.1 mmol, 95%).

According to the analysis of related databases, 887581-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem