Month: June 2021

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. 39538-68-6, name is 2-Methoxy-4-methylaniline, A new synthetic method of this compound is introduced below., Safety of 2-Methoxy-4-methylaniline

General procedure: In a threaded ACE glass pressure tube with a sealed Teflon screw cap equipped with a magnetic stirring bar, a mixture of 11a (0.200 g, 1.65 mmol), 12a (0.185 g, 1.65 mmol), p-TsOH (0.028 g, 0.16 mmol), and MS 4A (0.20 g) in toluene (10 mL) was stirred and heated at 130 C for 4.5 h under microwave irradiation (100 W). The solvent was removed under vacuum and the residue purified by column chromatography (silica gel, hexane-EtOAc, 98:2) to give 7a (0.32 g, 91%) as a brownishoil; Rf = 0.75 (hexane-EtOAc, 7:3).

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; Hernandez-Benitez, R. Israel; Zarate-Zarate, Daniel; Delgado, Francisco; Tamariz, Joaquin; Synthesis; vol. 49; 18; (2017); p. 4357 – 4371;,
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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 20781-20-8 as follows. COA of Formula: C9H13NO2

To a solution of 2,4-dimethoxybenzylamine (Sigma-Aldrich) (6.6 mL, 43.5 mmol) in DCM (85 mL) was added saturated aqueous sodium bicarbonate solution (85 mL) and the mixture was stirred vigorously at RT for 15 min. Stirring was stopped; then thiophosgene (6.6 mL, 87 mmol) was added via syringe to the bottom layer. The mixture was stirred at RT for 90 min then the aqueous layer was separated and the organic layer was washed with brine, dried over Na2S04 and concentrated in vacuo twice from DCM to give l-(isothiocyanatomethyl)-2,4- dimethoxybenzene

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KHAN, Tanweer; SMITH, Elizabeth; WILLIAMS, Peter; WISCOUNT, Catherine; MCKITTRICK, Brian; MCCAULEY, John; (72 pag.)WO2018/106519; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, category: ethers-buliding-blocks

To a solution of 3-bromo-5-fluoroanisole (500 mg, 2.44 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (64 mg, 2.56 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After reaching room temperature, 4-bromobenzaldehyde (542 mg, 2.93 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 80 C overnight. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was used in the next step without further purification. C14H12BrFO2; MW 311.

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; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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These common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, 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. SDS of cas: 2688-84-8

A solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40percent hydrobromic acid (50 ml) at 0° C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40percent hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5percent hydrochloric acid, 10percent potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45percent) was obtained by column purification of the crude intermediate using pet ether as eluent

The synthetic route of 2-Phenoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/15237; (2008); A1;,
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These common heterocyclic compound, 107622-80-0, name is (4-Phenoxyphenyl)methanamine, 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. name: (4-Phenoxyphenyl)methanamine

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

The synthetic route of (4-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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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. 6358-77-6, name is 5-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-methoxyaniline

A 50-mL round-bottom flask was charged with 5-bromo-2-methoxy aniline(Alfa Aesar, 1.00 g, 4.95 mmol), 3-chloro-4-methylphenylboronic acid (Acros, 1.69 g, 9.90 mmol), 1,1 ‘-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.81 g, 0.99 mmol), and purged with nitrogen. 1,4-Dioxane (37.1 ml) and an aqueous sodium carbonate solution (1.9 M, 12.4 mL) were introduced and the reaction mixture was warmed to 80 C. After 90 min, the reaction mixture was allowed to cool to ambient temperature and diluted with aqueous HCI solution (1.0 M, 25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 0 to 40% EtOAc in heptane with DCM as a 5% additive) to afford 3′-chloro-4-methoxy-4′-methyl-[l,l’-bipheny 1]-3-amine (1.03 g, 4.16 mmol, 84.0 % yield) as a tan solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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Reference 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.

The product of Example 33D (62 mg, 0.2 mmol) was treated with triethyl orthobenzoate (Aldrich, 0.5 mL) in DMF (1 mL) at 100° C. for 10 h. It was then concentrated. The title product was purified by preparative HPLC (Xterra.(TM)., column, Xterra RP-18, 5 mum, 30.x.100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10), (v. 90/10 to 10/90 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (40.0 mg, 50percent). 1H NMR (500 MHz, CD3OD) delta 1.52-1.64 (m, 1 H), 1.68-1.80 (m, 1 H), 1.80-1.92 (m, 1 H), 2.06-2.18 (m, 1 H), 2.25-2.31 (m, 1 H), 2.75-3.10 (m, 5 H), 3.39-3.49 (m, 1 H), 5.14-5.27 (m, 1 H), 7.55-7.66 (m, 3 H), 7.69 (dd, J=8.5, 1.8 Hz, 1 H), 7.81 (d, J=8.2 Hz, 1 H), 8.00 (d, J=1.5 Hz, 1 H), 8.27 (dd, J=8.1, 1.7 Hz, 2 H), 8.89 (s, 2 H) ppm; MS (DCl/NH3): 399 (M+H)+.

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:
Patent; Abbott Laboratories; US2005/137204; (2005); A1;,
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Synthetic Route of 22483-09-6, The chemical industry reduces the impact on the environment during synthesis 22483-09-6, name is 2,2-Dimethoxyethanamine, I believe this compound will play a more active role in future production and life.

Compound 3 (1.0 g, 6.82 mmol) was dissolved in aqueous NaOH (0.275 g in 20 ml water) to yield a clear solution. Aminoacetaldehyde dimethyl acetal (0.93 ml, 8.58 mmol) was added. The mixture was placed on an oil bath (120-130 C); foaming lasted for 3 h. The mixture was cooled. The resulting grey powder was recovered by filtration, washed with cold water, and dried under high vacuum to give 4 (yield 1.3 g, 88%). 1H NMR (D2O): 2.79 (s, 2H), 2.81 (s, 6H), 3.99 (t, J =5.4 Hz, 1H).

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, 2,2-Dimethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Laos, Roberto; Lampropoulos, Christos; Benner, Steven A.; Acta Crystallographica Section C: Structural Chemistry; vol. 75; 1; (2019); p. 22 – 28;,
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Adding a certain compound to certain chemical reactions, such as: 16728-64-6, name is 3-(Benzyloxy)propan-1-amine, 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 16728-64-6, HPLC of Formula: C10H15NO

Step 3 3-(3-(benzyloxy)propyl)-6-methoxyquinazoline-2,4(1H,3H)-dione To a solution of 6-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione (0.92 g, 4.77 mmol) in THF (10 mL) was added 3-(benzyloxy)propan-l-amine (0.94 g, 5.72 mmol) and then TEA (0.97 g, 9.54 mmol) dropwise. The reaction was heated at 80C for lh, cooled to RT and diluted with EA (20 mL) and water (10 mL). The organic layer was dried over Na2SC>4 and concentrated to a brown oil. The oil was dissolved in THF (10 mL), cooled to 0C, then triphosgene (565 mg, 1.91 mmol) was added. The reaction was stirred at RT for 30 min then TEA (389 mg, 3.82 mmol) was added. The reaction was stirred at RT for 2h and filtered. The filtrate was concentrated and dried to give 3-(3-(benzyloxy)propyl)-6-methoxyquinazoline-2,4(1H,3H)-dione (1.3 g, 80% yield) as a brown oil. LCMS: MH 341 and TR = 1.456 min. Used without further purification.

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, 3-(Benzyloxy)propan-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HYDRA BIOSCIENCES, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHENARD, Bertrand L.; GALLASCHUN, Randall J.; (73 pag.)WO2016/23826; (2016); A1;,
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150-78-7, name is 1,4-Dimethoxybenzene, 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: 150-78-7

Paraformaldehyde (Aldrich, 4.27 g, 144.75 mmol) and HBr/AcOH (Fluka, 33%, 30 mL) were added slowly to a stuffed solution of 1,4-dimethoxybenzene (Aldrich, 10.00 g, 72.37 mmol) in glacial acetic acid (Fisher, 50 mL). The mixture was stirred at 50C for one hour, allowed to cool to room temperature, and then hydrolyzed in water (200 mL). The white solid was collected by filtration, suspended in CHC13 (50 mL), and refluxed for 10 mm. After cooling to room temperature, the white solid was again collected by filtration and washed with water (15.75 g, 67%). NMR spectra were obtained experimentally to confirm the chemical structure of the resulting compound and its purity. NMR results were as follows: ?H NMR (300 MHz, CDC13) 6:6.88 (s, 2H), 4.54 (s, 4H), 3.87 (s, 6H) ppm.

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

Reference:
Patent; ROBERT BOSCH GMBH; MARUNIAK, Autumn; AHMAD, Habib; RAGHUNATHAN, Ashwin; JOHNSON, Christopher; KAVUSI, Sam; FOMINA, Nadezda; LANG, Christoph; (170 pag.)WO2017/5587; (2017); A1;,
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