Month: June 2021

Synthetic Route of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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.

General procedure: To a stirred solution of the respective N-carbamate-protected aminovicinal diol 4 (0.50 mmol, 1 equiv) in CH2Cl2 (10 mL, 0.05 M) were added BF3·OEt2 (50 muL, 0.050 mmol, 0.1 equiv, 1.0 M solution in CH2Cl2) and trimethyl orthobenzoate (0.13 mL, 0.75 mmol, 1.5 equiv) at r.t. The resulting mixture was refluxed or stirred at r.t. under N2 until TLC showed complete conversion of the substrate. The reaction was quenched with sat. aq NaHCO3 and extracted with EtOAc (2 ×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane/EtOAc) to give the desired product 5.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Park, Heemin; Kwon, Yongseok; Shin, Jae Eui; Kim, Woo-Jung; Hwang, Soonho; Lee, Seokwoo; Kim, Sanghee; Synthesis; vol. 49; 12; (2017); p. 2761 – 2767;,
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Reference of 33311-29-4, A common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, molecular formula is C9H13NO2, 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.

To a solution of compound 27-1 in DMF (50 mL) was added dropwise DIPEA (4.55 g, 35.23 mmol) and compound 27-1-1 (5 g, 30.2 mmol) under nitrogen atmosphere at 0 C., and the reaction solution was reacted at 0 C. for 0.5 h, followed by warmed to r.t. and reacted for another 1 h. The resulting reaction solution was diluted with EtOAc (50 mL) and washed with brine (30 mL×3). The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to give a residue was purified by column chromatography (3% to 8% of PE/EtOAc) to afford the title compound (360 mg, 26.3%) as white solid.

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; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
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Reference of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

1-(2-Bromoethoxy)-4-fluorobenzene (25.5 g (0.116 mol)) and N-ethylcyclohexylamine hydrochloride (28.5 g (0.174 mol)) were dissolved in ethanol (400 mL), and then potassium carbonate (48.7 g (0.35 mol)) and sodium iodide (44.1 g (0.232 mol)) were added to the solution. The mixture was stirred for 48 hours under heating at reflux, and the reaction mixture was returned to room temperature. The insoluble fraction was removed by filtration and the solvent was distilled away under reduced pressure. The residue was purified by a silica gel chromatography (petroleum ether: ethyl acetate = 6 : 1) and hydrogen chloride gas was passed into the resulting oil to precipitate a crystal, which was collected by filtration to obtain the target N-ethyl-N-[2-(4-fluorophenoxy)ethyl]cyclohexylamine hydrochloride (5.3 g, 17.6 mmol, yield 24%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Bromoethoxy)-4-fluorobenzene, its application will become more common.

Reference:
Patent; M’s Science Corporation; EP2357165; (2011); 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. 2525-16-8, name is 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Methoxy-3,4,5,6-tetrahydro-2H-azepine

I. 3-Methyl-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one 25 g 2-bromo-4-methylbenzoic acid was treated with 150 mL of 28% aqueous ammonia, 50 g gaseous ammonia, 1 g CuSO4 at 140 C. for 12 hours in an autoclave, then concentrated in vacuo, dissolved in a minimal amount of water, pH adjusted to 6 with 4N HCl. The precipitate was filtered, washed with ice cold water, and dried at 60 C. The residue was extracted with THF and concentrated in vacuo, giving a light brown crystalline solid. Yield of combined material: 14 g 4-methylanthranilic acid. 6.4 g of this acid was suspended with stirring in 100 mL toluene. 11 mL 1-Aza-2-methoxy-1-cycloheptene (1) (Aldrich) were added and the mixture was refluxed under a Dean-Stark trap for 12 hours. Then the toluene was removed by distillation in vacuo, followed by removal of excess (1) in vacuo (11 mm Hg) at 140 C. The dark brown residue crystallized. It was purified by column chromatography (6:1 chloroformethyl acetate) followed by recrystallization from hexane-ethyl acetate to give 7.1 g of pure 3-methyl-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one as white, shiny crystals.

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; Warner-Lambert Company; US5486512; (1996); A;,
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These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. Quality Control of p-Bromophenetole

A mixture of 4-bromophenetole (1.0 mmol), phenylboronic acid (1.2 mmol), organic solvents (6 mL), bases (2.0 mmol) and 0.5 mol % of catalyst was stirredat 80 C under air. After the reaction, the catalyst was separated by filtration. The filtrate was dried over Na2SO4 and filtered. The products were quantified by GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a 0.25mm × 30 m DB-WAX capillary column). The typical GCMS analysis program was as follows: initial column temperature 100 C, hold 2 min, ramp temperature to 280 C at 15 C/min, and hold for 5 min.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Zhi-Qiang; Yang, Xiao-Li; Ye, Yuan-Feng; Hao, Lin-Yun; Bulletin of the Korean Chemical Society; vol. 35; 4; (2014); p. 1121 – 1127;,
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Reference of 41789-95-1, 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 41789-95-1 as follows.

General procedure: To a solution of 2,6-bis(chloromethyl)pyridine (1 mmol) in anhydrous acetonitrile (10 mL) was added cesium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 5 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (100:1, v/v) to give the title compound as a colorless liquid or a white solid.

According to the analysis of related databases, 41789-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Related Products of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: A mixture of 2.73 mmol appropriate alkyl halide (i.e., 17a-c, or18a-c), 0.6 g K2CO3 (4.34 mmol), and 0.6 g NaI (4.00 mmol) in ACN(12 mL) was mixed for 5 min in a 30 mL microwave reaction vessel.Then, 8.2 mmol appropriate amine derivative (i.e., 1-6, as shown inScheme 3) was added and the resulting content was mixed foradditional 2 min. The reaction vessel was capped, and insertedinside the microwave instrument (i.e., A CEM Model Single ModeMicrowave Instrument) and heated for 32 min at 105 C at thedynamic mode of the instrument automatically calibrating theradiation and temperature balance with respect to the change inpressure. Then, acetonitrile was distilled out under vacuum andthe residue thus obtained was mixed with 20 mL of K2CO3 solution(5.0%) and this mixture was heated at 60 C for 1 h. Then the mixturewas cooled down to room temperature and the aqueous phasewas extracted 3 times with 20 mL of ethylacetate. Combinedorganic extracts were dried over MgSO4 and concentrated underreduced pressure to give the product (i.e., free base). The free basewas dissolved in 10 mL acetone and HCl gas was continuouslypassed until HCl salt precipitation took place.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Gulcan, Hayrettin Ozan; Unlu, Serdar; Esiringu, Ilker; Ercetin, Tugba; Sahin, Yasemin; Oz, Demet; Sahin, Mustafa Fethi; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5141 – 5154;,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. category: ethers-buliding-blocks

l-Bromo-2-(2-methoxyethoxy)ethane (1.83 g, 10 mmol, diluted in 10 mL of dried DMF) was added dropwise to a stirred mixture of tert- butyl 4-hydroxyphenethylcarbamate (2.61 g, 11 mmol) and NaH (0.44 g, 11 mmol, 60% dispersion in mineral oil) in dry DMF (40 mL) under N2 at 0 C. The reaction was stirred at room temperature for 14 h. After this time, the reaction mixture was stirred at 60 C for 8 h. The reaction was quenched with ice-water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography to afford the title compound as colorless oil (2.311 g, 68% yield). NMR (500 MHz, CDCb) S: 7.19- 7.01 (m, 2H), 6.93-6.81 (m, 2H), 4.58 (s, 1H), 4.13 (dd, J= 9.8, 4.9 Hz, 2H), 3.86 (dd, J= 9.5, 5.1 Hz, 2H), 3.79-3.67 (m, 2H), 3.65-3.53 (m, 2H), 3.40 (dd, J= 4.0, 1.8 Hz, 3H), 3.34 (s, 2H), 2.73 (s, 2H), 1.44 (s, 9H).

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Ether – Wikipedia,
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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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 54149-17-6

Example 1.2.1 4-Bromo-3,5-dimethylphenol (10.05 g, 50.0 mmol) and K2CO3 (9.0 g, 65.2 mmol) were stirred for 10 minutes in DMF (25 mL). 1-Bromo-2-(2-methoxyethoxy)ethane was added, and the reaction mixture was heated at 45 C. overnight under argon. After cooling to room temperature, the reaction mixture was poured into ~300 mL DCM; filtered off white solids. Flash column (silica; 100% hexane) gave 12.95 g (85% yield) of product 5.

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 54149-17-6.

Reference:
Patent; Nitto Denko Corporaton; US2010/308310; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, A new synthetic method of this compound is introduced below., Formula: C11H9BrO

The reaction route is as follows:250mL three-necked flask was added 2.66g (0.01mol)1,1-bis (4-aminophenyl) cyclohexane,10.65 g (0.045 mol) of 4-methoxy-1-bromonaphthalene,4.80 g (0.05 mol) sodium tert-butoxide,53g toluene.Nitrogen gas protection 0.09 g (4.0 × 10 -4 mol) of palladium acetate,0.462 g (8.0 × 10 -4 mol) Xantphos,The temperature was raised to 100 C to 108 C and refluxed for 10 hours.Completed the reaction,Add 50g water twice,Dried over anhydrous sodium sulfate,The solvent was removed under reduced pressure to give a tan solid.The above crude product was treated with THF,Ethanol (mass ratio of 3: 6) recrystallization,5.4g white powder was obtained,Yield: 60.5%.

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; CECEP Wanrun Co., Ltd.; Hu Zhenyu; Ren Huicai; Cao Yuan; Pang Maoyin; Chen Shuai; Tian Shaozhen; Wang Yonglei; Luo Wei; Hu Baohua; Meng Fanmin; (17 pag.)CN106565507; (2017); A;,
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