Tag: M.W=100-200

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 398-62-9 as follows. Formula: C8H9FO2

To a suspension of sulfur trioxide N, N-dimethylformamide complex (4. [108G,] 27 mmol) in 1,2-dichloroethane was added 4-fluoroveratrole (3.49g, 22 mmol) dropwise. The mixture was slowly heated to [85C] in an oil bath. After 2.5h, the solids had dissolved to afford a golden yellow solution. A trace of starting material was still present and heating was continued for a further 4.5h. The oil bath was removed and thionyl chloride (1.95 mL, 27 mmol) added dropwise. The mixture was heated 4h at [85C] and allowed to cool to room temperature. The solution was poured into water and extracted with dichloromethane [(3X50] mL), the combined organics washed with water, dried over magnesium sulfate and evaporated. Remaining traces of N, N-dimethylformamide were removed azeotropically with toluene to afford the product as an off-white solid that was used without further purification.

According to the analysis of related databases, 398-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-la Roche AG; WO2004/13120; (2004); A1;,
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Application of 38336-04-8,Some common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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.

To a solution of tert-butyl 4-((6-bromopyridin-3-yl)oxy)piperidine-1-carboxylate (200 mg, 0.280 mmol), 2-(benzyloxy)ethanamine (50.8 mg, 0.336 mmol), sodium 2-methylpropan-2-olate (81 mg, 0.840 mmol), and 2-(dicyclohexylphosphino)-2?,4?,6?-triisopropylbiphenyl (13.34 mg, 0.028 mmol) in THF (5 mL) was added tris(dibenzylideneacetone)dipalladium(0) (25.6 mg, 0.028 mmol). The reaction mixture was stirred at 70 C. for 15 h before cooling to RT and partitioning with water (10 mL) and EtOAc (10 mL¡Á3). The combined organic layers were washed with water (20 mL¡Á3), dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (1/1 EtOAc/petroleum ether) to provide the title compound.

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

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
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910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, 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. Computed Properties of C2H5BF3KO

In a 4 mL vial were combined NiCl2 dimethoxyethane adduct (3.4 mg, 0.015 mmol, 0.12 equivalents) and 4,4′-di-ter/-butyl-2,2′-dipyridyl (4.15 mg, 0.015 mmol, 0.12 equivalents) in /V,/V-di methyl acetamide (1.0 mL). Example 1G (60 mg, 0.13 mmol, 1.0 equivalents), potassium trifluoro(methoxymethyl)borate (58 mg, 0.39 mmol, 3.0 equivalents), cesium carbonate (105 mg, 0.32 mmol, 2.5 equivalents) and bis[3,5-difluoro-2-[5-(trifluoromethyl)-2- pyridyl] phenyl] iridium(l+); 2-(2-pyridyl)pyridine; hexafluorophosphate (4.3 mg, 0.004 mmol, 0.03 equivalents) were added, followed by dioxane (1.0 mL). The reaction was irradiated overnight using a 450 nm LED photoreactor. The reaction was filtered and purified by reverse-phase preparative HPLC on a Waters XBridge C8 5 pm column (75 mm x 30 mm). A gradient of methanol (A) and 25 mM ammonium bicarbonate buffer (pH 10) in water (B) was used, at a flow rate of 40 mL/minute (0- 0.5 minutes 15% A, 0.5-8.0 minutes linear gradient 15-100% A, 8.0-9.0 minutes 100% A, 9.0- 9.1 minutes linear gradient 100-15% A, 9.1-10.0 minutes 15% A) to afford 5-[3-(benzyloxy)-l- fluoio-7-(methoxymethyl)naphthalen-2-yl]- 1 / 2,5-thiadiazolidinc- 1, 1,3-trione (52.4 mg, 94% yield).

The synthetic route of 910251-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; FARNEY, Elliot; SHIROODI, Roohollah, Kazem; XIONG, Zhaoming; ZHANG, Qingwei, I.; O’CONNOR, Matthew; HALVORSEN, Geoff; ZHAO, Hongyu; BAUMGARTNER, Christina; FROST, Jennifer, M.; KYM, Phil; ABBOTT, Jason, R.; BOGDAN, Andrew; ECONOMOU, Christos; WANG, Xueqing; (375 pag.)WO2019/246513; (2019); A1;,
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Related Products of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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 Concentrated hydrochloric acid plus purified water (1) after dilution,Transfer to a 10L reactorWarm up to about 30C. Under nitrogen protection,The dimethylamino acetaldehyde diethyl acetal was slowly added dropwise to the diluted hydrochloric acid,About 2 hours after the addition,The reaction was stirred overnight at about 30C. MakeBefore use, neutralize to neutral with solid sodium carbonate,Inorganic salts are filtered away.

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-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; Hangzhou East China Pharmaceutical Group New Drug Institute Co., Ltd.; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Yin Jianming; Lv Yubin; Li Bangliang; (13 pag.)CN107141261; (2017); A;,
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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 437-83-2 as follows. name: 3-Fluoro-2-methoxyaniline

A mixture of 3-fluoro-2-methoxyaniline (1.0 g, 7.1 mmol) and K2CO3 (1.04 g, 7.8 mmol) in DMF (15 mL) was added 1-bromobut-2-yne (981 mg, 7.1 mmol) was stirred at r.t. overnight. The resulting mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-20% EtOAc in PE) to afford the title compound (552 mg, 40% yield) as a yellow oil. LC-MS (ESI): m/z (M+1) = 193.91.

According to the analysis of related databases, 437-83-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIIV HEALTHCARE UK LIMITED; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WEATHERHEAD, Jason Gordon; (225 pag.)WO2017/93938; (2017); 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 4,4-Diethoxybutan-1-amine

To 0.95 g 1-isocyanatonaphthalene (5.62 mmol) dissolved in 20 cm3 of dry benzene 0.90 g 4,4-diethoxybutan-1-amine (5.59 mmol) was added. The mixture was stirred at room temperature for 12 h. The precipitate was filtered off,washed with 10 cm3 benzene, and dried in vacuum(0.01 torr, 4 h, r.t.) to give 6 as white solid. Yield 1.63 g(88%); m.p.: 121-122 C (from ethanol); 1H NMR[600 MHz, (CD3)2SO]: d = 1.11 (6H, t, J = 6.86 Hz,CH3), 1.48-1.52 (2H, m, CH2), 1.56-1.60 (2H, m, CH2),3.14-3.17 (2H, m, CH2), 3.42-3.47 (2H, m, CH2),3.55-3.60 (2H, m, CH2), 4.50 (1H, t, J = 5.49 Hz, CH),6.56 (1H, t, J = 5.48 Hz, NH), 7.41 (1H, t, J = 7.96 Hz,CHAr), 7.49-7.55 (3H, m, CHAr), 7.88 (1H, d,J = 8.23 Hz, CHAr), 7.99 (1H, d, J = 7.68 Hz, CHAr),8.08 (1H, d, J = 8.23 Hz, CHAr), 8.44 (1H, s, NH) ppm;13C NMR [150 MHz, (CD3)2SO]: d = 15.8, 25.6, 31.4,39.5, 61.1, 102.6, 116.9, 121.8, 122.4, 125.8, 126.0, 126.2,126.4, 128.8, 134.2, 135.7, 156.1 ppm; MS (MALDITOF):m/z = 353 ([M+Na]+).

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:
Article; Smolobochkin, Andrey V.; Gazizov, Almir S.; Voronina, Julia K.; Burilov, Alexander R.; Pudovik, Michail A.; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 535 – 541;,
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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. 62257-15-2, name is 2-Fluoro-5-methoxyaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8FNO

2-Fluoronicotinic acid methyl ester (0.3 g, 1.934 mmol) and 2-fluoro-5-methoxyaniline(0.278 ml, 2.32 1 mmol) were heated by microwave irradiation at 130 C for 20 mm. SomeDCM was added and the mixture was washed twice with 1120. Organic phase was dried overNa2SO4, filtered and evaporated. Crude product was purified by trituration with diethylether. 0.324 g of the title compound was obtained.?H NMR (400 MHz, CDCJ3) oe ppm 3.82 (s, 3 H) 3.95 (s, 3 H) 6.49 (dt, 1 H) 6.78 (dd, I H) 7.03 (dd, I H) 8.27 (dd, I H) 8.33 (dd, I H) 8.42 (dd, 1 H) 10.42 (hr. s., I H).

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; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; VESALAINEN, Anniina; WO2015/144976; (2015); A1;,
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Electric Literature of 126829-31-0, The chemical industry reduces the impact on the environment during synthesis 126829-31-0, name is 2-Ethynyl-1,3-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

Example 29; [0139] l,3-Bis(2,6-diisopropylphenyl)-4-(2,6-dimethoxyphenyl)-lH-l,2,3-triazolium hexafluorophosphate (lOal). To a stirred suspension of triazene 8a (3.66 g, 10 mmol), 2,6- dimethoxyphenylacetylene 91 (3.24 g, 20 mmol), and anhydrous potassiumhexafluorophosphate (1.84 g, 10 mmol) in dry dichloromethane (50 mL) in the dark at -78C is added tert-butyl hypochlorite (1.66 mL, 15 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to roomtemperature. The contents are then filtered, and the solid residue is washed withdichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. Ihour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt lOai as an off-white solid (5.25 g, 78%). Analytical samples were obtained after recrystallization by vapor diffusion of diethyl ether in an acetonitrile solution of lOai. 1H-NMR ((CD3)2SO, 300 MHz): delta = 10.03 (s, 1H), 7.79 (t, J = 7.9 Hz, 1H), 7.64-7.57 (m, 3H), 7.54 (t, J = 7.9 Hz, 1H), 7.42 (d, J = 7.9 Hz, 2H), 6.78 (d, J = 8.5 Hz, 2H), 3.71 (s, 6H), 2.43 (sept, J = 6.8 Hz, 2H), 2.29 (sept, J = 6.8 Hz, 2H), 1.27 (d, J = 6.8 Hz, 6H), 1.17 (d, J = 6.8 Hz, 6H), 1.08 (d, J = 6.8 Hz, 6H), 0.99 (d, J = 6.8 Hz, 6H). 13C-NMR ((CD3)2SO, 75 MHz): delta = 158.4, 145.2, 144.7, 139.9, 136.4, 135.2, 133.3, 132.9, 130.2, 129.2, 125.0, 124.8, 104.7, 98.0, 56.9, 28.8, 28.6, 25.8, 23.8, 23.1, 21.7. HR-MS (ESI): Calcd. for C34H44N302 [M+]: 526.3428, found 526.3433.

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-Ethynyl-1,3-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BERTRAND, Guy; GUISADO-BARRIOS, Gregorio; BOUFFARD, Jean; DONNADIEU, Bruno; WO2011/139704; (2011); A2;,
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These common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, 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. Recommanded Product: 3-Methoxy-4-methylaniline

To 6.05 g of dichlorophenylborane dissolved in 40 ml of dichloromethane, at -20 C., are successively added 5.226 g of 3-methoxy-4-methylaniline dissolved in 50 ml of dichloromethane, and 13.4 ml of triethylamine dissolved in 25 ml of dichloromethane. After 30 minutes at -20 C., 5.412 g of 2,6-difluorobenzaldehyde dissolved in 60 ml of dichloromethane are introduced. After 24 hours at room temperature, the mixture is hydrolyzed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. To the oil obtained, dissolved in 80 ml of diethyl ether, are added 80 ml of 2 M sodium hydroxide solution and the mixture is left stirring for 18 hours. The phases are separated by settling and the organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with n-pentane to give 5.069 g of the expected product. 1H NMR delta in ppm (DMSO d6): 1.98 (s, 3H); 3.69 (s, 3H); 4.74 (s, 2H); 5.79 (d, 1H); 5.98 (d, 1H); 6.30 (s, 1H); 6.75 (s, 1H); 7.06 (m, 2H); 7.41 (m, 1H).

The synthetic route of 3-Methoxy-4-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); 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. 101-84-8, name is Diphenyl oxide, A new synthetic method of this compound is introduced below., Recommanded Product: 101-84-8

(1) diphenyl ether (44.2 g, 0.26 mol) was added into a 250 ml four-necked flask and 123.5 g (1.25 mol) of dichloroethane was added and stirred for 1 hour.Cool to -5 ~ 0 ,Bromine (21 g, 0.13 mol) was rapidly added dropwise and stirred for 1 hour. The mixture was cooled to -5~0 C and 30% hydrogen peroxide (15 g, 0.13 mol)With 0.5 to 1 hour dropwise addition and termination,The temperature is controlled between 0 and 5 DEG C, naturally heated to 25 DEG C after dropping, incubated for 32 hours between 27 DEG C and quenched with 49g of 15% sodium bisulfite, after the phase separation,Then washed with water to neutral, to distill dichloroethane distillation, distillation under reduced pressure before recovery of diphenyl ether, and finally collected 4-bromo-diphenyl ether 51.7g, yield 80.0%, content of 98.2%.

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; Binhai Extensive Chemical Co., Ltd.; Wu Fucai; (8 pag.)CN106957220; (2017); A;,
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