Month: April 2021

These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. name: 2-(2-Chloroethoxy)acetic acid

In a three-necked round-bottom flask under nitrogen atmosphere equipped with a mechanical stirrer, a thermometer, a condenser and a dropping funnel 6.87 g (0.05 mol) phosphorus trichloride and 10.75 g (0.05 mol) Amberlyst-15 (hydrogen form, dry) were mixed with 50 ml chlorobenzene . Slowly 6.90 g of (0.05 mol) 5-chloro-3- oxapentanoic acid was added drop-wise. After completed addition the reaction mixture was heated to 50 ¡ãC for 4 h. During the addition and reaction time the evolution of CO was observed. Then 10 ml water was added and the Amberlyst- 15 was filtered off. The solution was analyzed by ChiEta- and 31P-NMR spectroscopy and 4-Chloro-2-oxabutanyl-l-phosphonic acid observed at 58.9 percentw/w.

The synthetic route of 2-(2-Chloroethoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STRAITMARK HOLDING AG; BURCK, Sebastian, R., W.; NOTTE, Patrick; WO2013/17564; (2013); A2;,
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Application of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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: Dimethyl 5-hydroxyisophthalate (1, 6 mmol), 1,omega-dialkylating agent (18 mmol) and K2CO3 (60 mmol) were stirred in anhydrous DMF (60 mL) at a room temperature for 18 h. The reaction mixture was Celite filtered, washed with dichloromethane and toluene. The combined filtrates were evaporated to dryness and the residual colorless oil was chromatographed (dichloromethane, then dichloromethane:methanol, 100:1, v/v) to give a crude product which was a white solid. The yields ranged from 18 to 80%. Some reactants prepared as above have been obtained previously by diverse methods: dimethyl 5-(2-bromoethoxy)isophthalate (2a) [11], dimethyl 5-(5-bromopentoxy)isophthalate (2b) [12] and dimethyl 5-(3-bromopropoxy)isophthalate (2d) [13].

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

Reference:
Article; Gierszewski, Mateusz; Falkowski, Michal; Sobotta, Lukasz; Stolarska, Magdalena; Popenda, Lukasz; Lijewski, Sebastian; Wicher, Barbara; Burdzinski, Gotard; Karolczak, Jerzy; Jurga, Stefan; Gdaniec, Maria; Tykarska, Ewa; Sikorski, Marek; Mielcarek, Jadwiga; Goslinski, Tomasz; Journal of Photochemistry and Photobiology A: Chemistry; vol. 307-308; (2015); p. 54 – 67;,
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Application of 588-63-6, These common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)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: A solution of the appropriate aryloxyalkylbromides 9?16(5 mmol) commercially available or prepared as above-described,imidazole 7 or 1,2,4-triazole 8 (7.5 mmol), TEA (5 mmol) and catalyticamount of TBAB (0.1 g) in acetonitrile (3 mL) was heated undermicrowaves irradiation in a sealed vial at 100 C, 200 W, 150Psi, for 30?45 min. The solvent was removed in vacuo to give a residuewhich was suspended in water, alkalinized with NaOH 0.1 Nand extracted with dichloromethane (3 50 mL); the combinatedextracts were washed with water, dried, and evaporated to obtaina residue which was purified by flash column chromatography onsilica gel using ethyl acetate or ethyl acetate/methanol 9:1 as eluent.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salerno, Loredana; Pittala?, Valeria; Romeo, Giuseppe; Modica, Maria N.; Siracusa, Maria A.; Di Giacomo, Claudia; Acquaviva, Rosaria; Barbagallo, Ignazio; Tibullo, Daniele; Sorrenti, Valeria; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5145 – 5153;,
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Application of 160911-11-5, These common heterocyclic compound, 160911-11-5, name is 1-Fluoro-3-methoxy-5-methylbenzene, 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.

(40b) 1-Fluoro-5-methylphenol A solution of 1-fluoro-3-methoxy-5-methylbenzene obtained in Example (40a) (0.92 g, 6.56 mmol) and boron tribromide (1.0 M solution in methylene chloride, 8.53 mL, 8.53 mmol) in methylene chloride (20 mL) was stirred at 0C for 10 hours. Water (100 mL) was added to the reaction solution, followed by extraction with methylene chloride (100 mL). Then, the organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (hexane:ethyl acetate, 1:1) to obtain the title compound (0.83 g, yield: 99%) as a yellow oil. 1H-NMR (CDCl3, 400 MHz) delta: 2.06 (3H, s), 4.97 (1H, s), 6.37 (1H, dt, J = 2.4, 10.2 Hz), 6.44 (1H, s), 6.48 (1H, d, J = 8.6 Hz).

The synthetic route of 160911-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2138484; (2009); A1;,
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Synthetic Route of 1836-62-0,Some common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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.

A mixture of 9.7 g 4-(OXIRANE-2-YLMETHOXY)-9H-CARBAZOLE (II), 53.7 g of anhydrous hydrogen sulphate of 2-(2-METHOXYPHENOXY) ETHYLAMINE (III) and 28 g of anhydrous potassium carbonate in 200 ML ISOPROPANOL are, with intensive stirring, heated at 80 C for six hours. When the epoxide has reacted, the mixed salts are filtered off from the reaction mixture and isopropanol is distilled off from the filtrate. The obtained honey-like concentrate is diluted with heating in 50 ml of ethylacetate, the solution is cooled to the temperature of 40 C, it is inoculated and stirred at the temperature of 40 C for two hours. After the crystal precipitates, the mixture is cooled to the temperature of 0 C, and is kept like that with stirring for a minimum of four hours. After filtration and washing with cooled ethylacetate, 5.2 g of wet, crude Carvedilol is obtained (HPLC contents 95.2 area %, HPLC contents of the bis-derivative 2.8 area %).

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

Reference:
Patent; Zentiva, A.S.; WO2004/41783; (2004); A1;,
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Reference of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

3,3-diethoxypropan-1-amine (6 g, 40.76 mmol, 1.00 equiv) was dissolved in1,4-dioxane (30 mL) in the presence of TEA (4.45 g, 43.98 mmol, 1.08 equiv), then cooled to 0C. (Boc)20 (9.6 g, 43.99 mmol, 1.08 equiv) diluted in 20 mL of 1,4- dioxane was added drop-wise. The solution was agitated 2 hours at 0C then overnight at ambient temperature before being neutralised with 10 mL of water. The pH was adjusted to 5 with HC1 (1 %). The solution was extracted 3 times with 50 mL of EtOAc.The organic phases were combined, dried over sodium sulfate, filtered and concentrated to yield 8.21 g (81 %) of compound 1ZD in the form of a pale yellow oil.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174064; (2014); A1;,
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7664-66-6, name is 4-Isopropoxyaniline, 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. Recommanded Product: 4-Isopropoxyaniline

Into a stirringmixture of ethyl acetate (20 mL), tetrahydrofuran (4 mL), water(4 mL), sodium carbonate (0.8 g, 7.9 mmol, 0.6 equiv.), and 4-isopropoxyaniline (2.0 g, 13.2 mmol, 1 equiv.), phenyl chloroformate(2.3 g, 14.5 mmol, 1.1 equiv.) was added dropwise at 0 C.The reaction was stirred at room temperature overnight, then itwas evaporated under reduced pressure and the resultant wasadded into 20 mL water, the precipitate was filtered and washedwith water, then dried under vacuum to afford 3.2 g of 13a as whitesolid; yield: 90%; MS (ESI) m/z: 286.1 [MH], 308.1 [MNa].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yingxiu; Ye, Tianyu; Xu, Le; Dong, Yuhong; Luo, Yong; Wang, Chu; Han, Yufei; Chen, Ke; Qin, Mingze; Liu, Yajing; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Electric Literature of 6943-97-1, 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. 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

(16-3) Synthesis of [5-(2-{4-[3-(3-methoxyphenyl)propoxy]-3-trifluoromethylphenyl}ethyl)-2,2-dimethyl-1,3-dioxan-5-yl]carbamic acid t-butyl ester (compound 16-3) Reference Example compound 2-6 (500 mg) was dissolved in N,N-dimethylformamide (10 ml), potassium carbonate (493 mg) and compound 16-2 (328 mg) were added, and the mixture was stirred at 80C for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (800 mg) as a white solid. 1H-NMR(CDCl3) delta (ppm): 1.42(3H, s), 1.44(3H, s), 1.47(9H, s), 1.93-1.98(2H, m), 2.08-2.12(2H, m), 2.51-2.56(2H, m), 2.81(2H, t, J=7.5Hz), 3.69(2H, d, J=11.7Hz), 3.76(3H, s), 3.89(2H, d, J=11.7Hz), 3.99(2H, t, J=6.0Hz), 4.98(1H, brs), 6.72-6.84(4H, m), 7.19(1H, t, J=7.5Hz), 7.24(1H, d, J=1.8Hz), 7.36(1H, d, J=1.8Hz).

The chemical industry reduces the impact on the environment during synthesis 1-(3-Bromopropyl)-3-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2168944; (2010); A1;,
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Some common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-methylaniline, 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. Recommanded Product: 2-Methoxy-4-methylaniline

General procedure: To a magnetically stirred ice-bath cooled solution of the selected succinic monoamide derivative (4 mmol) in anhydrous dioxane (20 ml) neat oxalyl chloride was added (8 mmol). After stirring over 30 min the reaction mixture was warmed to room temperature. Two hours later, the reaction mixture was re-cooled to 0 C in ice bath followed by drop wise addition of the particular aromatic amine (4 mmol) in pyridine (10 mL) to the reaction mixture. After stirring over 30 min the reaction mixture was warmed to room temperature and allowed to stir over 24 h. Subsequently, the reaction was carefully quenched with saturated sodium bicarbonate solution (200 mL). Finally, the mixture was filtered to offer the products as whitish to gray solids that were re-crystallized from acetone (see Scheme 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39538-68-6, its application will become more common.

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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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 168971-68-4 as follows. Product Details of 168971-68-4

n-Butyl lithium (6.17 mL, 9.87 mmol) was added drop-wise at -78 C. to a solution of 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (2.13 g, 8.22 mmol) in diethyl ether (16.5 mL). The reaction was stirred for 30 minutes before drop-wise addition of N-methoxy-N-methylacetamide (1.272 g, 12.34 mmol). The reaction was stirred for 5 minutes at -78 C. then warmed to room temperature and stirred for 30 minutes. The solution was quenched with saturated NH4Cl, extracted with EtOAc, dried with Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash silica gel chromatography, eluting with 10% EtOAc in heptanes provided 1-(2-fluoro-4-(trifluoromethoxy)phenyl)ethanone as a clear oil (1.118 g, 61%)

According to the analysis of related databases, 168971-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Hitchcock, Stephen; Lam, Betty; Monenschein, Holger; Reichard, Holly; (41 pag.)US2016/145218; (2016); A1;,
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