Month: July 2021

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 38380-85-7 as follows. name: 1-Bromo-4-cyclopropoxybenzene

Step 1 : A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for 2 hours. The solution was quenched with NH4Cl (aq. 1 mL) at – 78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 * 15 mL). The organic layer was dried with anhydrous Na2S04, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 min (method 2), m/z = 162.8 [M + H]+.

According to the analysis of related databases, 38380-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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Related Products of 854391-95-0,Some common heterocyclic compound, 854391-95-0, name is Bis(4-methoxybenzyl)amine hydrochloride, molecular formula is C16H20ClNO2, 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.

Preparation of intermediate II-22; A mixture of 2-chloro-5-bromopyrimidine (1.0 g, 5.16 mmol), N-(4- methoxybenzyl)(4-methoxyphenyl)methanamine hydrochloride, (cas 854391-95- 0) (1.59 g, 5.418 mmol) and DIPEA (2.68 mL, 15.48 mmol) in dry dioxane (10 mL) was heated for 1 h at 160C under microwave irradiation. On cooling, the mixture was diluted with EtOAc (200 mL) and the organic phase was washed with saturated aqueous NaHC03 (50 mL), brine (50 mL), dried (MgS04) and the solvent removed in vacuo to give a residue that was purified by column chromatography (hexane/EtOAc mixtures -20:1 to 10:1- as eluent) to give desired product as a white solid (1.81 g, 85% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(4-methoxybenzyl)amine hydrochloride, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. Formula: C6H15NO2

A mixture of 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl) amine (372 mL, 335.5 mg, 2.52 mmol), HOBt-H20 (459 mg, 3.00 mmol), and EDC-HC1 (575 mg, 3.00 mmol) were stirred together in DMF (20 mL) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned with EtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHC03 and brine. The solution was dried over anhydrous Na2S04, filtered and concentrated. Purification by radial flash chromatography (Si02, 10/1 CHCb-MeOH) afforded 228.7 mg (53% yield) of Example 4 as an orange foam: lH NMR (300MHz, CDC1 ), 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), 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCL3)? 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 muMu in PBS) abs = 394 nm. Fluorescence (100 muiotaeta) lambda6Chi = 394 nm

The synthetic route of Bis(2-methoxyethyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIBEACON INC.; DORSHOW, Richard, B.; ROGERS, Thomas, E.; (90 pag.)WO2016/183351; (2016); 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. 22236-08-4, name is 3-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-08-4

General procedure: A two neck round bottom flask under argon equipped with acondenser was charged with aldehyde 4 (1.0 equiv.) and 4-chloroaniline 3l (1.1 equiv.) in 2-pentanol [0.3 M] and stirred atreflux for 2 h. The tetronic acid 5 (1.1 equiv.) in 2-pentanol (minimumamount) was then added at reflux. After another 10 min atreflux, the third component aniline 3 (1.0 equiv.) was added neat.The reaction mixture was refluxed for an additional 30 min. Allvolatiles were evaporated under vacuum and the crude product purified by recrystallization in ethanol or by flash chromatographyon silica gel

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; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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Application of 578-57-4, 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. 578-57-4, name is 1-Bromo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

n-BuLi (3.5 ml of a 1.6 M solution in hexane) was added with stirring at 0 C to a solution of 2-bromoanisole (1.0 g, 5.34 mmol) in dry hexane (10 ml) and the mixture was allowed to stir at room temperature. After 2 h stirring the n-butyl bromide formed in the reaction mixture was evaporated under reduced pressure without introduction of air. Dry THF (10 ml) was added followed by the addition of the finely ground selenium powder (0.42 g, 5.34 mmol) at 0 C. It was stirred for 4 h. It was poured to the ice-cooled saturated NaHCO3 solution and O2 gas was passed to the mixture in a moderate rate for 15 min. The compound was extracted with diethyl ether and dried with anhydrous Na2SO4. The solvent was evaporated to obtain yellow-colored solid. The compound was purified in flash chromatography using petroleum ether and ethyl acetate as solvent. It was characterized by NMR spectroscopy. Yield: 0.58 g (31%), 1H NMR (CDCl3), delta (ppm): 3.91 (s, 6H, OCH3), 6.80-6.83 (d, 2H, ArH), 6.85-6.89 (m, 2H, ArH), 7.19-7.23 (m, 2H, ArH), 7.53-7.55 (d, 2H, ArH); 13C NMR (CDCl3), delta (ppm): 56.4, 110.6, 119.1, 122.4, 128.6, 131.0, 157.3; 77Se NMR (CDCl3), delta (ppm): 328. ESI-MS: m/z: calcd for C14H13O2Se2 [M+Na]+: 396.9222; found: 397.0495.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bhowmick, Debasish; Mugesh, Govindasamy; Tetrahedron; vol. 68; 51; (2012); p. 10550 – 10560,11;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

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

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
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Adding a certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2752-17-2, COA of Formula: C4H12N2O

Mixed nanosized TiO2-SiO2 oxide (0.27 g, 1.9 mmol) was added to a solution of acetoacetic ester (2) (3.75 g,28.8 mmol), 1,5-diamino-3-oxapentane (1a) (1.00 g, 9.6 mmol), and toluene (6 ml). The reaction mixture was stirred for 20 h at 90C. After the reaction was complete (TLC control, eluent 5:4:1 EtOAc-hexane-CHCl3), the nanosized oxide was separated by centrifugation, and toluene was removed by distillation. The obtained oil was purified by silica gel column chromatography, using CHCl3 as eluent, and dried under ambient conditions. Yield 2.33 g (74%), yellow oil. IR spectrum, nu, cm-1: 1141 (nuas, –Alk); 3291 (N-H); 1652,1505 (-O-N); 2930, 2978 (Alk-). 1H NMR spectrum,delta, ppm: 1.12-1.14 (6H, m, 2CH3); 1.90 (6H, s, 2CH3); 3.35-3.39 (4H, m, 2NCH2CH2); 3.51-3.55 (4H, m, 2NCH2CH2); 3.92-3.97 (4H, m, 232); 4.34-4.35 (2, m, 2); 8.59 (2H, s, 2NH). Found, %: 58.46; 8.43; N 8.69.16H28N2O5. Calculated, %: 58.51; 8.59; N 8.53.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Radionova, Elena S.; Fedorova, Olga V.; Titova, Yulia A.; Rusinov, Gennady L.; Charushin, Valery N.; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 478 – 482; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 478 – 482,5;,
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Application of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, 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 solution of 1,4-dimethyl-3-formylcarbazole (500 mg, 2.2 mmol) in benzene (15 mL) and 2,2-diethoxyethylamine (330 mg, 2.5mmol) was placed in a flask. The mixture was refluxed for 2 h. After the reaction, the solvent was evaporated under the reduced pressure. MeOH (15 mL) was added to the residue. NaBH4 (800 mg, 22mmol) was then added slowly, and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated under the reduced pressure. The residue was extracted with CHCl3 and dried over Na2SO4, andconcentrated under reduced pressure. A solution of the residue in a mixture of MeCN (10 mL) andpyridine (1 mL) was placed in a flask. After the solution was stirred at rt for 0.5 h, 2-nitrobenzenesulfonylchloride (1.0 g, 4.5 mmol) was added, and the reaction mixture was stirred at rt for 24 h. After thereaction, the solvent was evaporated under reduced pressure. The crude product was recrystallized from MeOH, affording N-(2,2-diethoxyethyl)-N-((1,4-dimethyl-9H-carbazol-3-yl)methyl)-2-nitrobenzenesulfonamide (85%, 1.0 g); yellow solid; mp 175.0-176.0 C; 1H NMR (500 MHz, CDCl3) delta 1.46 (6H, t, J= 7 Hz), 2.41 (3H, s), 2.73 (3H, s), 3.41-3.46 (4H, m), 3.61-3.64 (2H, m), 4.56 (1H, t, J = 5.5 Hz), 4.88(2H, s), 7.07 (1H, s), 7.21-7.26 (1H, m), 7.36-7.42 (2H, m), 7.47 (1H, d, J = 8 Hz), 7.52 (1H, d, J = 8 Hz),7.60 (1H, d, J = 8 Hz), 7.77 (1H, d, J = 8 Hz), 8.03 (1H, brs), 8.15 (1H, d, J = 8 Hz); 13C NMR (CDCl3,125 MHz) delta 15.3, 15.9, 16.5, 49.6, 50.6, 63.4, 102.2, 110.6, 116.8, 119.5, 121.9, 122.8, 123.7, 123.8,124.3, 125.1, 128.7, 130.4, 130.8, 131.1, 132.8, 134.4, 138.4, 139.6, 147.8; MS (FAB+) m/z 525 [M+];HRMS (FAB+): calcd for C27H31N3O6S (M+) 525.1933, found 525.1921.

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-Diethoxyethanamine, its application will become more common.

Reference:
Article; Sato, Naoya; Kawai, Yu; Akaba, Yosuke; Honma, Shoji; Sakai, Norio; Konakahara, Takeo; Heterocycles; vol. 92; 4; (2016); p. 664 – 679;,
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Related Products of 150-78-7, These common heterocyclic compound, 150-78-7, name is 1,4-Dimethoxybenzene, 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 starting compound (0.5-1.2 mmol) in DMF-H2O (95:5, v/v, 8-12 mL) mixture was added NBS (4.0-4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20%, 20-30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product.

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Natarajan, Palani; Vagicherla, Vinuta Devi; Vijayan, Muthana Thevar; Tetrahedron Letters; vol. 55; 24; (2014); p. 3511 – 3515;,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 171290-52-1

Cul (0.053g, 0.2mmol) was added to the degassed solution of 5-Iodo-N-(2-methyl-6- nitrophenyl)pyrimidin-2-amine (lg, 2.8mmol) and l-ethynyl-3,5-dimethoxybenzene (0.5g, 3.0mmol) in DMF (5mL) followed by the addition of tetrakis (0.32g, 0.2mmol) in a sealed tube. Stirred the reaction mass for 10 min and added DIPEA (0.75mL, 4.2mmol) and heated the resultant reaction mass to 80 C for 2h. Reaction mass was filtered through celite and washed the celite bed with ethyl acetate. The organic layer washed with water followed by brine, dried over Na2S04, filtered and concentrated. The residue was purified by 60-120 silica gel column chromatography to afford desired title compound (0.7g, 66%). LCMS: m/z = 391.1 (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 171290-52-1.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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