Month: December 2020

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, 702-24-9

A solution of p-methoxybenzylmethylamine (1.11 g; 7.34 mmol) and EtOH (10 mL) was added to a solution of 3,4,6-trichloropyrazine (1.28 g; 6.99 mmol), TEA (0.983 mL; 6.99 mmol) and anhydrous EtOH (20 mL) and the reaction stirred overnight at room temperature. The solvent was evaporated and the residue partitioned between EtOAc and H2O. The phases were separated, the water washed with EtOAc, and the combined EtOAc solutions washed with water and brine. The solution was dried (MgSO4), filtered and evaporated. The product was purified by silica gel chromatography and eluted with an EtOAc:hexane mixture (5:95–>30:70) to yield 89 as a white solid (1.3 g; 62percent).

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, 4-Methoxy-N-methylbenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

7252-83-7, A common compound: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90 C. for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H2O (200 mL), adjusted to pH 10 with saturated NaHCO3 aqueous solution and extracted with DCM (200 mL*3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60%).

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-Bromo-1,1-dimethoxyethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; Zhang, Yingjun; Zhang, Jiancun; Wang, Xiaojun; Lin, Runfeng; Cao, Shengtian; Wang, Zhaohe; Li, Jing; US2015/87639; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

10578-75-3, A common compound: 10578-75-3, name is 2-(Benzyloxy)ethanamine hydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

2,4-Dichloro-6,7-dimethyl-3-nitropyridine (26.89 g, 121.7 mmol), anhydrous N,N-dimethylformamide (400 mL), anhydrous triethylamine (48.84 mL), and the benzyloxyethylamine hydrochloride salt (27.4 g, 146.0 mmol) from Part B were combined under nitrogen and heated to 90 C. for 20 minutes, 60 C for 1 hour, and then 90 C. for 1 hour. The reaction was complete as determined by TLC analysis using 8/2 hexane/ethyl acetate. The reaction mixture was concentrated under reduced pressure, and the resulting orange solids were triturated with water. The resulting solids were filtered off and recrystallized from ethyl acetate. Recrystallized solids were rinsed with hexane and dried under vacuum at 50 C. for 30 minutes to provide 21.8 g of yellow fluffy solid for use in the next step. NMR analysis confirmed the N-[2-(benzyloxy)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine and a minor amount of residual salts.; Under a nitrogen atmosphere, triethylamine (40.4 mL, 290 mmol) was added to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (12.0 g, 58.0 mmol), prepared according to the general method of Part A of Example 1 using 2,4-dihydroxy-6-methyl-3-nitropyridine in lieu of 2,4-dihydroxy-5,6-dimethyl-3-nitropyridine, in anhydrous N,N-dimethylformamide (DMF) (200 mL). To the resulting dark brown solution was added 2-(benzyloxy)ethylamine hydrochloride (11.97 g, 63.76 mmol), and the mixture was stirred at room temperature for 23 hours. The volatiles were then removed under reduced pressure, and the residue was mixed with water and ethyl acetate. The organic layer was washed with water (3¡Á200 mL), aqueous sodium bicarbonate (2¡Á200 mL), and brine (3¡Á250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The crude product (18.1 g) was purified by column chromatography on silica gel (700 g, eluting with 80:20 hexane:ethyl acetate) to provide an oil which was triturated with 80:20 hexane:ethyl acetate. The resulting crystals were isolated by filtration and dried to provide 4.7 g of [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine as a yellow solid.

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-(Benzyloxy)ethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, molecular formula is C8H10FNO, 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. 123652-95-9

Compound 33; To a solution of compound 32 (0.185 mmol, 100 mg, 1.0 equiv.) in NMP (2 ml) was added 3- fluoro-4-methoxybenzylamine (1.850 mmol, 287 mg, 10 equiv.). The reaction mixture was heated to 100 0C and stirred overnight. Mixture was then poured into H2O and extracted withEtOAc. The combined organic layers were washed with water and brine, dried (Na2SC>4), filtered and concentrated in vacuo. 70 mg of compound 33 was obtained in 62% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123652-95-9, its application will become more common.

Reference:
Patent; N.V. ORGANON; PHARMACOPEIA INC.; WO2008/51826; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

In a 25 mL single neck flask, the intermediate 4 (0.4 g, 1.21 mmol), (3- methoxyphenyl)-N-methylmethanamine (1.09 g, 7.23 mmol), Cul (0.023 g, 0.12 mmol) and l-methylpyrrolidin-2-one (3 mL) were added and the resulting mixture was heated at 150 0 C for 12 h and worked up. The reaction mixture was partitioned in dichloromethane/water and the organic layer was separated. The organic phase was dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by prep-HPLC to obtain the pure 7-(N-(3-methoxybenzyl)-N-methylamino)-l-benzyl-6-fluoro-l, 4-dihydro-4- oxoquinoline – 3-carboxylic acid (25 mg); Yield: 4.63%; H NMR (400 MHz, CDCb): delta 15.0 (s, IH), 8.77 (s, IH), 8.01 (d, J=14, IH), 7.33 (s, 3H), 7.22-7.26 (t, IH), 7.04 (d, J=18.4, 2H), 6.82 (d, J=7.2, IH), 6.70-6.74 (m, 2H), 6.52 (d, J=5.6, IH), 5.30 (s, 2H), 4.43 (s, 2H), 3.71- 7.76 (m, 3H), 2.92(s, 3H); MS(ESI): 447.0(M+H); HPLC: 98.0%.

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 41789-95-1.

Reference:
Patent; NIROGYONE THERAPEUTICS, INC.; SANDANAYAKA, Vincent; WU, Qiong; (80 pag.)WO2016/81464; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7. 5414-19-7

To a room temperature mixture of the [T-BUTYL-2- ( {4- [4- (2-] ethoxyethoxy) phenyl] phenyl) sulfonyl) acetate product (4) from Part C (800 mg, 1.9 mmol) in 8 mL DMF was added 18-crown-6 (150 mg, 0.6 mmol), potassium carbonate (1.3 g, 9.5 mmol), and bis (2-bromoethyl) ether (480 mg, 2.1 mmol). The mixture was stirred at room temperature for 18 hr. Subsequently, no starting material (4) was detectable by HPLC. The resulting mixture was concentrated, diluted in cold ether, and filtered to produce 800 mg (86% yield) of the desired compound (5). LCMS: [[M+NA] =] 513.2.

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 1-Bromo-2-(2-bromoethoxy)ethane.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/811; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 450-91-9, name is 4-Fluoro-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 450-91-9

Step 1: 2-bromo-4-fluoro-6-methoxyaniline To a solution of 4-fluoro-2-methoxyaniline (14.4 g, 0.1 mol) in 300 mL of dry DMF was added NBS (17.8 g, 0.1 mol) in small portions at 0-5¡ã C. under nitrogen, then the resulting mixture was stirred at room temperature overnight. The mixture was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-bromo-4-fluoro-6-methoxyaniline (28 g crude).

The synthetic route of 450-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arrington, Kenneth L.; Burgey, Christopher; Gilfillan, Robert; Han, Yongxin; Patel, Mehul; Li, Chun Sing; Li, Yaozong; Luo, Yunfu; Lei, Zhiyu; US2014/100231; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

60789-54-0, Adding a certain compound to certain chemical reactions, such as: 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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 60789-54-0.

3-Benzyloxybutyl-cyclopent-2-enone A solution of a Grignard reagent was prepared following the procedure described in the synthesis of 3-(5-hexenyl)cyclopent-2-enone, using Mg turnings (302 mg, 12 mmol), THF (11 mL), and benzyl 4-bromobutylether (2.75 g, 11.3 mmol).

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, ((4-Bromobutoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Massachusetts Institute of Technology; US6465664; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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. 59557-91-4

(0900) Under the protection of nitrogen gas, 4-bromo-2-methoxyaniline (15 g, 74.24 mmol) was dissolved in 1,4-dioxane (250 mL), and a solution of sodium bicarbonate (15.8 g, 188.07 mmol) in water (150 mL) was added. At 0 C., carbobenzoxy chloride (19.1 g, 111.96 mmol) was added dropwisely to the reaction system. After the addition, the reaction was carried out at room temperature for 20 min. TLC detection showed that raw materials disappeared. The mixture was extracted with ethyl acetate (100 mL¡Á3). The organic phases were combined, washed with saturated saline solution (100 mL¡Á2), dried with anhydrous sodium sulfate, and concentrated in vacuum. The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether=1:5) to get the title compound as a white solid (15 g, yield: 60%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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.

Synthesis of 3-fluoro-4-methoxybromobenzene Into a flask of 5 l were charged 384 g (3.04 mol) of 2-fluoroanisole and 2.5 l of chloroform, to which was added dropwise 504 g (3.16 mol) of bromine over about 3 hours while cooling on an ice water bath at 10 C. The resulting mixture was stirred at room temperature over a night and heated under reflux for 8 hours. After the air cooling, the product was added with 1 l of water and 50 g of sodium bisulfite and sufficiently shaken to separate into two layers. The resulting organic layer was washed with an aqueous solution of 5% sodium hydrogen carbonate and further with 1 l of water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and distilled under a reduced pressure (4 mmHg, bp: 93-96 C.) to obtain 585 g (yield: 94%) of 3-fluoro-4-methoxybromobenzene.

The synthetic route of 1-Fluoro-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Mining Co., Ltd.; US5098602; (1992); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem