Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 116557-46-1, name is 3-Bromo-2-methoxyaniline, 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 116557-46-1, Recommanded Product: 116557-46-1

A suspension of 3-bromo-2-methoxyaniline (500 mg, 2.47 mmol), bis(pinacolato)diboron (755 mg, 2.97 mmol) and potassium acetate (729 mg, 7.42 mmol) in 1,4-dioxane (8 mL) was sparged with nitrogen for 5 min. Pd(dppf)Cl2·DCM (173 mg, 0.21 mmol) was added and the mixture was heated under reflux for 2.5 h then cooled to room temperature. The reaction was diluted with DCM (35 mL) and washed with water (35 mL). The organic phase was concentrated under reduced pressure then purified by flash column chromatography, eluting with 0-100% EtOAc in isohexane, to return 49h (358 mg, 58%) an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 6.72-6.83 (m, 3H), 4.80 (s, 2H), 3.64 (s, 3H), 1.28 (s, 12H).

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; Newton, Rebecca; Bowler, Katherine A.; Burns, Emily M.; Chapman, Philip J.; Fairweather, Emma E.; Fritzl, Samantha J.R.; Goldberg, Kristin M.; Hamilton, Niall M.; Holt, Sarah V.; Hopkins, Gemma V.; Jones, Stuart D.; Jordan, Allan M.; Lyons, Amanda J.; Nikki March; McDonald, Neil Q.; Maguire, Laura A.; Mould, Daniel P.; Purkiss, Andrew G.; Small, Helen F.; Stowell, Alexandra I.J.; Thomson, Graeme J.; Waddell, Ian D.; Waszkowycz, Bohdan; Watson, Amanda J.; Ogilvie, Donald J.; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 20 – 32;,
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3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, 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. Application In Synthesis of 2,2-Diethoxy-N,N-dimethylethanamine

Synthesis Example B6Synthesis of 12H-benzofuranyl[3,2-a]carbazole (compound 6)Compound 5 (2.8 g, 1 eq.) is added to acetic acid (30 ml) and heated to reflux. (Dimethylamino)acetaldehyde diethyl acetal (95percent; 20.3 g, 10 eq.) is added dropwise in portions to the solution.The reaction is stirred at reflux overnight.Then further (dimethylamino)acetaldehyde diethyl acetal (95percent; 2.0 g) is added and stirred further at reflux after 3 h.Subsequently, the flask contents are diluted with CH2Cl2 at room temperature and washed in a separating funnel with distilled water and NaCl (saturated).Organic phase is dried with Na2SO4 and concentrated. LC (SiO2, 15:85 ethyl acetate/cyclohexane) gives the product 6 (1.92 g, 62.2percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.88 (br s, 1H), 8.16 (d, 1H), 8.12 (d, 2H), 7.66 (d, 1H), 7.62 (d, 1H), 7.42-7.53 (m, 4H), 7.31 (dd, 1H).

The synthetic route of 3616-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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Electric Literature of 645-36-3, These common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, 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.

2,2-Diethoxyethylamine (430 muL, 2.95 mmol) and Na2CO3 (0.285g, 2.69 mmol) were added to a stirred soln of pyrimidine 717 (0.645g, 2.69 mmol) in i-PrOH (20 mL). After 5 min, H2O (50 mL) was added and the product was extracted with CH2Cl2 (2 × 50 mL). The organic layers were combined, washed with H2O (2 × 20 mL), dried(Na2SO4), and concentrated. The residue was purified by flash chromatography[silica gel, hexane-benzene (1:1); Rf = 0.15] to give a yellow solid; yield: 0.40 g (44%); mp 71.5-73.5 C.IR (KBr): 3364 (NH) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.28 (t, J = 7.2 Hz, 6 H, 2 × CH3),2.58 (s, 3 H, SCH3), 3.61 (dq, 2J = 9.3 Hz, 3J = 7.2 Hz, 2 H,2 × CHAHBCH3), 3.73-3.85 (m, 4 H, NCH2 and 2 × CHAHBCH3),4.69 (t, J = 5.4 Hz, 1 H, OCH), 8.17 (br s, 1 H, NH).13C NMR (75 MHz, DMSO-d6): delta = 14.5, 15.7, 44.3, 62.3, 99.8,124.6, 152.6, 154.6, 173.0.Anal. Calcd for C11H17ClN4O4S: C, 39.23; H, 5.09. Found: C,39.21; H, 5.07.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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Application of 54149-17-6, These common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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.

2,7-dibromofluorene (Sigma Aldrich) (15.7 g, 0.048 mol) was dissolved in anhydrous tetrahydrofuran (150 mL) and cooled to 5 C. under argon atmosphere. Sodium tert-butoxide (10.5 g, 0.109 mol) was added portionwise, giving a deep red colour. After completion of addition, the reaction mixture was stirred at room temperature for 20 minutes. A solution of 1-bromo-2-(2-methoxyethoxy)ethane (Sigma Aldrich) (20 g, 0.109 mol) in anhydrous THF (50 mL) was added dropwise. The solution turned dark purple and an exotherm to 30 C. was observed. The reaction mixture was stirred at room temperature for 72 hours then diluted with water and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate (2*). The combined organic layers were washed with water and brine then dried (Na2SO4) and filtered. Concentration of the filtrates in vacuo followed by purification of the residue by dry flash chromatography (0 to 40% ethyl acetate in heptane) gave 2,7-dibromo-9,9-Bis[2-(2-methoxyethoxy)ethyl]-9H-fluorene as a yellow oil (10 g, 40%). 1H NMR (300 MHz, CDCl3) 7.52-7.42 (m, 6H), 3.27 (m, 10H), 3.16 (m, 4H), 2.76 (m, 4H), 2.34 (m, 4H).

Statistics shows that 1-Bromo-2-(2-methoxyethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 54149-17-6.

Reference:
Patent; Wuhan Xinqu Chuangrou Optoelectronics Technology Co., Ltd.; SIMMS, Michael James; OGIER, Simon Dominic; (47 pag.)US2019/131533; (2019); 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. 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, A new synthetic method of this compound is introduced below., Computed Properties of C10H14O3

To a two-necked round-bottom flask containing a solution of (CH2O)n (0.030 g, 1 mmol) and HCl (37%, 0.5 mL) in AcOH (5 mL) was added, by means of a syringe pump (rate=10 mL/h), a solution of 3,4,5-trimethoxy-toluene (0.182 g, 1 mmol) in AcOH (5 mL) over a period of 30 min at 20 C. The solution was stirred for another 30 min. The mixture was then poured into EtOAc (40 mL) and washed with H2O (1×40 mL) and a saturated NaHCO3 aqueous solution (3×40 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a transparent oil (0.209 g) containing 2-chloromethyl-3,4,5-trimethoxytoluene in 77% yield, and 2,2′,3,3′,4,4′-hexamethoxy-6,6′-dimethylbiphenyl-methane (23%) as the main by-product. Purification of 2-chloromethyl-3,4,5 trimethoxytoluene by alumina or silica gel chromatography was fruitless since 2-chloromethyl-3,4,5-trimethoxytoluene, in the presence of traces of H2O, reacted to give the corresponding benzyl alcohol. Using the NMR spectra of a pure sample of 2,2′,3,3′,4,4′-hexamethoxy-6,6′-dimethylbiphenylmethane as reference (see Supporting Information in Appendix E), the characteristic signals of 2-chloromethyl-3,4,5-trimethoxytoluene were detected in the NMR spectra of the final reaction mixture. 1H NMR (200 MHz, CDCl3, ppm): delta2.37 [s, 3H, CH3], 3.84-3.96 [9H, 3×OCH3], 4.68 [s, 2H, CH2], 6.52 [s, 1H, ArH]. 13C NMR (200 MHz, CDCl3, ppm): delta18.7, 38.6, 55.7, 60.6, 61.4, 109.3, 121.9, 133.4, 140.0, 152.2, 153.4. MS m/z (%): 230 (31), 215 (1), 195 (100), 180 (40), 165 (5), 150 (12), 137 (12), 120 (6), 105 (7), 91 (5), 77 (6), 66 (5).

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; Bjorsvik, Hans-Rene; US2008/287702; (2008); A1;,
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Related Products of 41365-75-7, The chemical industry reduces the impact on the environment during synthesis 41365-75-7, name is 1-Amino-3,3-diethoxypropane, I believe this compound will play a more active role in future production and life.

Step 1 : N-(3,3-diethoxypropyl)pyridine-3-carboxamide (2a) Pyridine-3-carbonyl chloride (10 g, 56.2 mmoles, 1 eq.) was dissolved in DMF (50 mL) and CH3CN (200 mL) with TEA (19.5 mL, 140.4 mmoles, 2.5 eq.). 3,3-diethoxypropan-1 -amine (10.35 g, 70.2 mmoles, 1 .25 eq.) in CH3CN (20 mL) was added at 0C. The solution was stirred overnight then was concentrated, diluted with DCM and washed with sat. NaHC03 and brine. The organic phase was then separated, dried over sodium sulphate and evaporated in vacuum to obtain N-(3,3-diethoxypropyl)pyridine-3- carboxamide 2a (6.8 g, Y= 45%). LC-MS (M-H+): 253.0.

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-Amino-3,3-diethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; GAROFALO, Barbara; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; CORSO, Gaia; MAGARO’, Gabriele; FURLOTTI, Guido; IACOANGELI, Tommaso; (108 pag.)WO2016/96631; (2016); A1;,
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Related Products of 41365-75-7, A common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

Step 1: tert-Butyl (3,3-diethoxypropyl)carbamate A solution of di-tert-butyl dicarbonate (6.74 g, 31.0 mmol) in DCM (50 mL) was added to a solution of 1-amino-3,3-diethoxypropane (5.0 g, 34.0 mmol) in DCM (50 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with 10% aqueous potassium hydrogen sulfate and the organic phase dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the title product (8.13 g, 100%). 1H NMR (400 MHz, CDCl3): delta 5.00 (s, 1H), 4.56-4.53 (m, 1H); 3.69-3.62 (m, 2H); 3.54-3.46 (m, 2H); 3.24-3.20 (m, 2H); 1.84-1.80 (m, 2H); 1.49 (s, 9H); 1.23-1.19 (m, 6H).

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

Reference:
Patent; Chiesi Farmaceutici S.p.A.; RANCATI, Fabio; Linney, Ian; Knight, Chris; Schmidt, Wolfgang; US2014/163066; (2014); A1;,
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Electric Literature of 43229-65-8, The chemical industry reduces the impact on the environment during synthesis 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, I believe this compound will play a more active role in future production and life.

1) A compound of the formula II (178.1 g) and a compound of the formula III (161.7 g) are added to a reaction flask and stirred.Heat to internal temperature 90-100 C, reaction 2-3h, to internal temperature 120-130 C, reaction 2-3h to complete(HPLC detection, the peak area is calculated according to the normalization method, and the compound of the formula III is less than 10%, the reaction is considered complete), and the compound of formula IV is obtained, 320.5g,After cooling to 70 ± 5 C, it was dissolved in anhydrous ethanol (220 mL) to prepare for the next step.

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, N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Health Yuan Breathe Pharmaceutical Engineering Co., Ltd.; Shanghai Fangyu Health Pharmaceutical Technology Co., Ltd.; Yu Xiong; Xiao Duzheng; Zheng Guangji; Chen Yuhua; Yuan Xilun; (28 pag.)CN109535027; (2019); 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-1,1-dimethoxyethane

[000398] A mixture of Compound 24A (10 g, 89 mmol), 2-bromo-l,l- dimethoxyethane(15 g, 89 mmol), K2C03 (18.4 g, 134 mmol), KI (100 mg) in DMF (100 mL) was stirred at reflux for 3 h, then cooled to rt, and filtered. The filtrate was added water (200 mL), extracted with ethyl acetate (100 mL x 2), washed with water (100 mL x 3), brine (100 mL x 1), dried over Na2S04, concentrated, and purified by silica gel column chromatography (ethyl acetate in petroleum ether, 10% v/v) to render Compound 24B (15 g, yield 85%>) as a colorless liquid. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.46 (s, 6H), 3.96 (d, J= 5.2 Hz, 2H), 4.71 (t, J= 5.6 Hz, 1H), 6.90 (m, 2H), 7.26 (m, 2H).

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
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Related Products of 886762-08-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 886762-08-9 name is 5-Bromo-2-(trifluoromethoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
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