Month: August 2021

Related Products 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.

Example 6 To a mixture of 16.6 g of compound according to example 2 in toluene (600 ml) trimethyi ortobenzoate (120 ml) and camphenesulphonic acid (4 g) were added. The mixture was stirred vigorously at rt for 3 h, then 80 % acetic acid (160 ml) was added. After further 1 h of stirring the biphasic mixture obtained was separated, the organic phase was diluted with toluene (600 ml), washed with water (800 ml) and sat. NaHC03 (2 x 600 ml), dried, filtered and evaporated. The resulting oil was dropped into 600 ml of heptane and seeded. The white crystalline compound was filtered, washed and dried to yield 1 10.3 g of acceptor (a compound of general formula 6, wherein R|= Bn, R2= 4-chlorobenzoyl, R3= benzoyl, ORj in beta). [a]D = +17.13 (c = 1 DCM), Mp 156-157 C.

Statistics shows that (Trimethoxymethyl)benzene is playing an increasingly important role. we look forward to future research findings about 707-07-3.

Reference:
Patent; GLYCOM A/S; BAJZA, Istvan; DEKANY, Gyula; AGOSTON, Karoly; PEREZ, Ignacio Figueroa; BOUTET, Julien; HEDEROS, Markus; HORVATH, Ferenc; KOVACS-PENZES, Piroska; KROeGER, Lars; ROeHRIG, Christoph; SCHROVEN, Andreas; VRASIDAS, Ioannis; TRINKA, Peter; KALMAR, Laszlo; KOVACS, Imre; DEMKO, Sandor; AGOSTON, Agnes; RISINGER, Christian; WO2011/100980; (2011); A1;,
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37466-89-0, name is 3-Methoxybenzene-1,2-diamine, 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. SDS of cas: 37466-89-0

A solution of 2,3-diaminoanisole (400 mg, 2.89 mmol) and chloroacetic acid (557 mg, 6 mmol) in 4 N HCl was heated to 105 C. for 16 hours. The mixture was then cooled, neutralized (to a pH of 8) with aqueous sodium bicarbonate, and extracted twice with dichloromethane. The organic fractions were then dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel flash chromatography using a 1:1 mixture of hexanes:ethyl acetate as an eluent to give 1H-2-chloromethyl-4-methoxybenzimidazole as a yellow foam in a yield of 386 mg (68%). 1H NMR (CDCl3) delta 3.96 (s, 3H), 4.85 (s, 2H), 6.71 (m, 1H), 7.19 (m, 2H).

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bridger, Gary; Kaller, Al; Harwig, Curtis; Skerlj, Renato; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; McEachern, Ernest J.; Atsma, Bem; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher D.; Di Fluri, Maria R.; US2004/19058; (2004); A1;,
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Application of 111-95-5,Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl)amine (372 mul_, 335.5 mg, 2.52 mmol), HOBt-H2O (459 mg, 3.00 mmol), and EDC-HCI (575 mg, 3.00 mmol) were stirred together in DMF (20 m._) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned withEtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHCO3 and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. Purification by radial flash chromatography (SiO2, 10/1 CHCI3-MeOH) afforded 228.7 mg (53% yield) of Example 1 as an orange foam: 1H NMR (300MHz, CDCI3), delta 4.92 (s, 4 H), 3.76 (apparent t, J = 5.4 Hz, 4 H), 3.70 (apparent t, J = 5.6 Hz, 4 H), 3.64 (apparent t, J = 5.4 Hz, 4 H)1 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5- 95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 3.14 min on 30 mm column, (M+H)+ = 429. UV/vis (100 muM in PBS) lambdaabs = 394 nm. Fluorescence (100 nm) lambdaex = 394 nm.lambdaem = 550 nm.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
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Reference of 332-48-9, The chemical industry reduces the impact on the environment during synthesis 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 6 In a similar manner to Example 3, a mixture of 4-(dimethylaminomethyliminomethyl)piperidine (6.42 g), 2-bromoethyl 4-fluorophenyl ether (8.3 g), triethylamine (5.3 ml) and toluene (20 ml) was heated on a steam bath for 16 hours to give 4-aminomethyl-1-[2-(4-fluorophenoxy)ethyl]piperidine as an oil.

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-(2-Bromoethoxy)-4-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KNOLL Aktiengesellschaft; US5760035; (1998); A;,
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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. 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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