Ethers-buliding-blocks

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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline

Example 8 (Z)-1-(3-hydroxy-4-methoxyphenyl)-3-((2-methoxy-5-((Z)-3,4,5-trimethoxystyryl)phenyl)amino) prop-2-en-1-one (10q) To a stirred solution of (Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)aniline (5d) (100 mg, 0.317 mmol) in ethanol (5 ml) 1-(3-hydroxy-4-methoxyphenyl)prop-2-yn-1-one (6q) (55.85 mg, 0.317 mmol) was added. The reaction mixture was stirred at a temperature of 24 C. for 4 h and the reaction was monitored by TLC using hexane/ethyl acetate (6:4) as a solvent system. Then appropriate water was added to reaction mixture. A yellow colour solid appears which was filtered and washed with ethanol. (yield: 110 mg, 70%); mp: 88-91 C.; 1H NMR (CDCl3, 300 MHz) deltadelta (ppm): 3.71 (s, 6H), 3.85 (s, 3H), 3.94 (s, 6H), 5.68 (s, 1H), 5.91 (d, J=8.3 Hz, 1H), 6.49 (d, J=13.6 Hz, 4H), 6.79 (d, J=8.3 Hz, 1H), 6.96-6.87 (m, 2H), 7.12 (s, 1H), 7.24-7.18 (m, 1H), 7.50 (d, J=6.7 Hz, 2H), 12.06 (d, J=12.1 Hz, NH); FABMAS:(M+H)=478.

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; Council of Scientific and Industrial Research; Ahmed, Kamal; Gajjela, Bharath Kumar; Anver, Basha Shaik; Vangala, Santhosh Reddy; Mahesh, Rasala; US2015/322009; (2015); A1;,
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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 450-91-9 as follows. Safety of 4-Fluoro-2-methoxyaniline

In a flask equipped with a water cooled condenser a phenyl amine (1.0 equiv.), bis(2- chloroethyl)amine hydrochloride (1.5 equiv.), potassium carbonate (1.5 equiv.) and sodium iodide (0.4 equiv.) were suspended in diglyme. The resulting reaction mixture was allowed to heat to reflux over a period of one hour and allowed to stir at reflux for an additional 2.5 hours. It was then partitioned between dichloromethane and distilled water. The pH of the water layer was adjusted to basic pH (9-10) with 5% aqueous sodium hydroxide. The water phase was extracted thrice with dichloromethane. The combined organic layers were washed once with 10% aqueous sodium thiosulfate to remove iodine, dried over anhydrous sodium sulfate and the solvent removed in vacuo. The product was purified by column chromatography in 2M ammonium/methanol and dichloromethane mixtures.; l-(4-Fluoro-2-methoxy-phenyl)-piperazine was synthesized from 4-Fluoro-2-methoxy- phenylamine (151.5 mg, 1.07 mmol), bis(2-chloroethyl)amine hydrochloride (287.4 mg, 1.61 mmol), potassium carbonate (222.5 mg, 1.61 mmol) and sodium iodide (64.5 mg, 0.43 mmol) in diglyme. Column chromatography 10% 2M ammonia/methanol in dichloromethane provided the product as a dark brown oil (89.8mg, 40%). 1H NMR (300 MHz, CDCl3): delta(ppm) 6.78-6.90(m, IH), 6.57-6.65(m, 2H), 3.86(s, 3H), 3.14(broad t, 2H), 3.05(broad t, 4H), 2.95(t, IH), 2.72(broad t, 2H).

According to the analysis of related databases, 450-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/71730; (2006); A1;,
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Application 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.

To a stirred mixture of 2,2-diethoxy-IV,JV-dimemylcthanapiiine (15.7 g, 97.5 mmol) and water (16.4 mL) at room temperature under a nitrogen atmosphere was added aq. 37percent HCl (16.4 mL, 195 mmol). After addition the mixture was stirred at 40°C (bath) for 25 hours. It was then cooled to 0 °C (bath) to give Solution A. KOH (14.0 g, 250 mmol) was dissolved in water (75 mL) at room temperature under a nitrogen atmosphere. It was then cooled to 0 °C (bath) to give Solution B. To a stirred heterogeneous mixture of compound 160 (19.97 g, 39.0 mmol) at room temperature under a nitrogen atmosphere was added a rninirnurn amount of DMA (60 mL) to give a homogeneous solution. LiCl (1.65 g, 39.0 mmol) was then added and the resulting mixture was stirred atO °C (bath) for 15 min. The cold Solution B was then added and the reaction was stirred at 0 °C for 2 min. Cold Solution A was then added and the final reaction mixture was stirred further at 0 °C under a nitrogen atmosphere. The reaction was monitored by TLC (DCM/MeOH=10:l). After 30 min more KOH (s) (5.0 g, 89 mmol) was added and the reaction was stirred further at 0 °C for 1.5 hours. It was then poured into water (1,000 mL). Petroleum ether (1,000 mL) was added and the mixture was stirred at room temperature for 20 min. The petroleum ether layer was decanted before more petroleum ether (600 mL) was added and the mixture was again stirred for 15 min. The solid was collected by filtration, washed with water (5×200 mL) and dried under reduced pressure over silica gel/KOH to give (2J3)-iV-[4-(3-bromo-4-fluoroanilino)pyrido[3,4-Lambda(|pyrimidin-6-yl]-4- (dimethykmino)-2-butenamide (161) (16.9 g, 97percent).

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; AUCKLAND UNISERVICES LIMITED; SMAILL, Jeffrey, Bruce; PATTERSON, Adam Vorn; DENNY, William, Alexander; WILSON, William Robert; LU, Guo-Liang; ANDERSON, Robert, Forbes; LEE, Ho Huat; ASHOORZADEN, Amir; WO2010/104406; (2010); A1;,
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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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-2-(2-bromoethoxy)ethane

Bis-(2-bromoethyl) ether (2.04 ml, 16.2 mmol) and potassium succinimide (1.50 g, 8.10 mmol) were dissolved in dimethylformamide. The solution was heated to 80C and stirred for 19 hours. The solvent was removed under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, dried over anhydrous sodium sulfate, and purified by a silica gel column chromatography (hexane:ethyl acetate = 5:1) to obtain a bromo compound (1.64 g, 68.0%). ESI-MS (m/z) 299 (M+H)+.

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 5414-19-7.

Reference:
Patent; Ajinomoto Co., Inc.; EP2157092; (2010); A1;,
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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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 19056-40-7

Intermediate 235; Diethyl IFf 4-bromo-3-methoxyphenyl)amino1methylenelmalonate; To a solution of 4-bromo-3-methoxyaniline (25 g, 0.12 mol) in CH3CN (150 mL) was added diethylethoxymethylene malonate (27 mL, 0.13 mol). After 20 hours, the solvent was removed under reduced pressure and the residue dissolved in EtOAc. Hexane was added, and the resulting precipitate collected to give 37 g (80percent) off-white solid. 1H NMR: 10.68 (d, 1 H), 8.38 (d, 1 H), 7.52 (d, 1 H), 7.20 (d, 1 H), 6.91 (dd, 1 H), 4.20 (q, 2 H), 4.11 (q, 2 H), 3.86 (s, 3 H), 1.23 (m, 6 H); m/z: 372.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/119046; (2007); A1;,
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Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

N-(3-Benzyloxy-phenyl)guanidine: To a suspension of 3-benzyloxyphenylamine (20.0 g, 100.35 mmol) in 1,4-dioxane (150 mL) was added cyanamide (7.39 g, 175.95 mmol) followed by 4M HCl in 1,4-dioxane (44 ml, 176.00 mmol). The resulting suspension was heated at 80° C. overnight then cooled to ambient temperature and 6N NaOH (35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml in vacuo and the resulting precipitate was collected by filtration. The solid product was dried under vacuum overnight to afford23.8 g in 98.4percent yield. 1H NMR (MeOH-d4) delta 6.4-7.5 (m, 9H), 5.1 (s, 2H)

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cao, Jingrong; Green, Jeremy; Moon, Young-Choon; Wang, Jian; Ledeboer, Mark; Harrington, Edmund; Gao, Huai; US2003/96816; (2003); A1;,
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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 768-70-7 as follows. Application In Synthesis of 3-Ethynylanisole

1.0 mmol of m-methoxyphenylacetylene, 1.5 mol of sodium azide, 1.2 mmol of benzyl bromide, and 0.1 mmol of cuprous iodide were added to 4002.0 mL of polyethylene glycol, and the reaction was stirred at room temperature for 35 minutes, and the reaction was completed. The product was treated by column chromatography V petroleum ether: V ethyl acetate = 3: 1 to obtain 1-benzyl-4- (3-methoxy) phenyl1,2,3-triazole. The product was a white solid. Yield: 92%.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Leshan Normal University; Zeng Hongyao; Xia Liewen; Wang Yinghong; (13 pag.)CN110498772; (2019); A;,
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Reference of 1978-39-8, These common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-methoxyaniline, 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.

8-Fluoro-5-methoxy-2H-benzoreiri ,2,41thiadiazin-3(4H)-one 1 ,1 -dioxide (lnt-12) (2152) A 250 mL round-bottomed flask was charged with chlorosulfonyl isocyanate (2.058 ml) in nitropropane (20 ml) to give a colorless solution at -40 C under nitrogen. After 10 min, a solution of 5-fluoro-2-methoxyaniline (2.72 g) in nitropropane (10 ml) was added to the reaction mixture. After 10 min, the reaction was warmed to 0 C. After 1 h, aluminum chloride (3.21 g) was added to the reaction mixture. After 5 min, the reaction mixture was warmed to 1 10 C. After 30 min, the reaction mixture was poured in ice/water (400 mL) and stirred for 1 h. The solids were filtered and washed with water. The solids were placed in drying oven overnight at 50 C to obtain the titled compound (2.3 g). LCMS m/z 247.1 (M+H).

The synthetic route of 1978-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
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Application of 74654-07-2,Some common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, molecular formula is C7H17NO3, 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 2 (1000 mg, 1.33 mmol), 1,3-dicyclohexylcarbodiimide (140 mg, 2.03 mmol), and allylamine (150 mg, 2.33 mmol) in 50 cm3 of dichloromethane and 1-hydroxybenzotriazole hydrate (225 mg, 1.46 mmol) dissolved in 15 cm3 of tetrahydrofuran were mixed together and stirred at 0 C for 1 h. After this time, the reaction mixture was stirred at room temperature for a further 24 h. Then the solvents were distilled under reduced pressure to dryness. The residue was suspended in hexane and filtered off to remove the 1,3-dicyclohexylurea by-product. The filtrate was evaporated under reduced pressure and purified by Dry Column Vacuum Chromatography on silica gel (Fluka type 60) to give 3a as a colourless solid (893 mg, 85% yield). Pure compound 3a was dissolved in acetonitrile. The solution was allowed to evaporate at room temperature. After several days the crystals were formed in 57% yield.

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-(2-Methoxyethoxy)ethoxy)ethanamine, its application will become more common.

Reference:
Article; Huczynski, Adam; Janczak, Jan; Stefanska, Joanna; Antoszczak, Michal; Brzezinski, Bogumil; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4697 – 4702;,
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Electric Literature of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 30 mL flamed-dried flask equipped with stir bar and a nitrogen-filled balloon were added 2,2,6,6-tetramethylpiperidine (1.2 equiv) and THF (12 mL). After cooled to 0 C with an ice waterbath, n-BuLi (2.5 M in hexane, 1.2 equiv) was added dropwise and the reaction was stirred at 0 C for 0.5 h. To a 100 mL flame-dried flask equipped with a stir bar and a nitrogen-filled balloon were added THF (30 mL), benzyne precursor (1 equiv), and corresponding ketene silyl acetals9 (1.5 equiv) and was cooled to 78 C with an acetone-dry ice bath before in situ generated lithium tetramethylpiperidine was added dropwise. The reaction was monitored and aqueous NH4Cl was added upon disappearance of the benzyne precursor. After warming to rt, the reaction mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and concentrated under reduced pressure. Acetonitrile (30 mL) was added to the concentrated reaction system and cooled to 0 C with an ice-water bath followed by slow addition of hydrofluoric acid (27.6 M, 10 equiv). Upon completion, the reaction was heated to 40 C overnight before water (100 mL) was added. The mixture was extracted with ethyl acetate (30 mLx3), washed with brine, and dried with Na2SO4. The combined organic extract was concentrated under reduced pressure and purified by column chromatography on silica gel to afford the following compounds. 4.6.2. 8-Ethyl-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (10). Compound 10 was obtained as colorless oil (876 mg) from 6a and tert-butyl((1-methoxybut-1-en-1-yl)oxy)dimethylsilane in 62% yield, Rf=0.8 (Hexane/EtOAc=5:1); 1H NMR (400 MHz, CDCl3) delta 7.40 (dd, J8.4, 7.1 Hz, 1H), 6.99 (d, J7.1 Hz, 1H), 6.78 (d, J8.4 Hz,1H), 4.13-4.06 (m, 4H), 1.98-1.72 (m, 2H), 1.04 (t, J7.5 Hz, 3H). 13C NMR (101 MHz, CDCl3) delta 188.9 (s), 156.0 (s), 153.5 (s), 137.5 (s), 131.1(s), 116.0 (s), 114.6 (s), 65.0 (s), 59.7 (s), 23.3 (s), 11.5 (s). IR: gamma 2963, 2934, 2876, 2359, 2340, 1766, 1602, 1574, 1482, 1455, 1435, 1277, 1157, 1123, 1020, 941, 799 cm-1. HRMS calcd for C16H14NaO2[MNa]: 261.0886, found: 261.0879.

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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen; Savage, Nikolas A.; Dong, Guangbin; Tetrahedron; vol. 70; 27-28; (2014); p. 4135 – 4146;,
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