Tag: M.W=100-200

Reference of 321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5-Bromo-2-chlorobenzoyl chloride 9b (124 g, 0.49 mol)Was dissolved in dichloromethane (600 mL)Cooled to -5 C,2-fluoroanisole (61.8 g, 0.49 mol) was added,Anhydrous aluminum chloride (133 g, 1.0 mol) was added in portions,The resulting mixture was stirred at room temperature for 4 hours.The reaction solution is poured into crushed ice,Extracted with dichloromethane (400 mL x 2)The combined organic phases were washed successively with saturated sodium bicarbonate solution (300 mL)And saturated brine (300 mL)Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,To the residue was added anhydrous ethanol (500 mL) and stirred at 0 C for 30 minutes. The solid was collected by suction filtration,The title compound 9c was obtained as a white solid (129 g, 77%).

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, 1-Fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Gu Zheng; Wu Wuyong; Qu Tong; Tan Haoxiong; Kang Panpan; Deng Bingchu; (48 pag.)CN106892948; (2017); A;,
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Reference of 578-57-4, A common heterocyclic compound, 578-57-4, name is 1-Bromo-2-methoxybenzene, molecular formula is C7H7BrO, 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.

The 186 mg (1mmol) 2 – bromoanisole, 186 mg (2mmol) aniline, 9.05 mg (0.05mmol) Cu (OAc)2, 36.1 mg (0.1mmol) ligand L3, 489mg (1.5mmol) Cs2CO3, 2 ml MeOH, adding 10 ml reaction tube, sealing, 60 C reaction under the condition of 3h. After the stop of the reaction, water, extracted with ethyl acetate, washing, saturated salt water washing, after drying with anhydrous sodium sulfate, filtered, the filtrate is distilled under reduced pressure, purification by silica gel chromatography separation column column, shall be 2 – methoxy – N – phenylaniline 175 mg, yield 88%.

The synthetic route of 578-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Wan Yiqian; Ding Xiaomei; Huang Manna; Zhu Xinhai; Yi Zhou; CN106883132; (2017); A;,
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Related Products of 41365-75-7, 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 41365-75-7 as follows.

1.1 N-(3,3-Diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as described in EP609058) were dissolved in 49 mL of DCM and 12 mL of THF. 11.4 mL of DIPEA, 5.84 g of HOBt, 7.07 g of EDC and 5.45 g of 3,3-diethoxy-propylamine were added sequentially. The mixture was stirred for 23 h at rt, diluted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using Hept/EtOAc from 3/1 to 0/1 as eluant to yield 7.25 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide as a yellowish oil.1H-NMR (CDCl3): 7.04 (s, 1H), 4.51 (t, 1H), 3.45-3.7 (m, 4H), 3.43 (s, 4H), 3.32 (s, 6H), 3.30 (dd, 2H), 1.79 (dd, 2H), 1.19 (t, 6H), 1.12 (s, 3H).

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hilpert, Kurt; Hubler, Francis; Renneberg, Dorte; US2011/207815; (2011); A1;,
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Application of 37466-89-0, 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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Methoxy-2-trifluoromethyl-1H-benzimidazole The compound of Example 11 (6.49 g) was dissolved in trifluoroacetic acid (75.0 mL) under ice cooling, followed by stirring for 5 hours under the condition of heating under reflux. After evaporating the solvent under reduced pressure, the residue was dissolved in ethyl acetate and poured into a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated out, washed with saturated brine, and then dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the resulting solid was suspended in hexane and collected by filtration to obtain the desired product (8.69 g) as a yellowish brown powder. 1H-NMR (CDOl3, 400 MHz): delta 4.01 (3H, s), 6.89 (1H, d, J=8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 7.32 (1H, t, J=8.0 Hz).

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, 3-Methoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; EP2168960; (2010); A1;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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