Category: ethers-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 1978-39-8, name is 5-Fluoro-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 1978-39-8, Computed Properties of C7H8FNO

General procedure: A primary amine (17.8 mmol) was dissolved/suspended in acetonitriie (50 ml) and then heated to reflux temperature. Then 2,6-lutidine (20 ml, 173 mmol) was added. A solution of DMP3C-BF4 (5.04 g, 9.88 mmol) was dissolved in acetonitriie (250 ml) and then added slowly dropwise (1 drop per 5-10 s) to the hot solution of the phenol compound. The addition was allowed to proceed overnight (16 h). The red reaction mixture was analyzed by MALDI-TOF (dithranol matrix) and this analysis indicated that no starting material was present. The reaction mixture was allowed to cool down, and then poured into an acidified KPF6 solution (10 ml 2 M HCI in 1500 ml 0.2 M KPF6) upon vigorous stirring. A red precipitate formed and the suspension was gen-tly stirred for 15 min and then filtered . The filtrate was washed with HCI solution (2 M), then with water, and finally with heptane until the heptane phase was nearly colorless. The red sticky mass was dissolved in a minimum of CH2CI2 through the filter. The product was precipitated with heptane and filtered off and washed with heptane (2 x 100 ml). The product was dissolved in a minor amount of acetonitrile and poured onto diethyl ether upon stirring. The red precipitate was allowed to form for 15 min, filtered off, and then washed with ether (2 x 100 ml). The red sticky product was collected and dissolved in CH2CI2. The CH2CI2 was removed by evaporation yielding 17 g of red-gray fine powder. The red powder was suspended in pure water and stirred overnight. The red powder was filtered off, washed with water, and sucked dry. The sticky red product was dissolved in acetonitrile through the funnel and then the solvent was removed by evaporation. The red powder was collected and dried on an oil pump for 1 day.

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Reference:
Patent; KØBENHAVNS UNIVERSITET; LAURSEN, Bo V.; ROSENBERG, Martin; SØRENSEN, Thomas Just; WO2015/58777; (2015); A1;,
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16452-01-0, name is 3-Methoxy-4-methylaniline, 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. Safety of 3-Methoxy-4-methylaniline

Step A 4-Methyl-3-methoxyphenylhydrazine A stirred mixture of 100.0 g (0.73 mole) of 4-methyl-3-methoxyaniline in 800 mL of concentrated hydrochloric acid was cooled to -5 C. A solution of 501.5 g (0.73 mole) of sodium nitrite in 250 mL of water was added slowly while maintaining the temperature of the reaction mixture below 0 C. The resultant mixture was stirred at -5 C. for 30 minutes. A cold solution of 330.0 g (1.46 mole) of tin (II) chloride dihydrate in 360 mL of concentrated hydrochloric acid was added over one hour. After complete addition the resultant mixture was allowed to warm to room temperature. A solid precipitate formed and was collected by filtration and stirred in 200 mL of water. This mixture was neutralized with 50% aqueous sodium hydroxide, and extracted with toluene. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 58.0 g of 4-methyl-3-methoxyphenylhydrazine as an oil.

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US4806145; (1989); 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a solution of 5-bromo-2-fluoroanisole (200 mg, 0.98 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (24 mg, 0.98 mmol, 1 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After reaching room temperature, 6-bromopyridin-2-yl carboxaldehyde (182 mg, 0.98 mmol, 1 equiv) was added and the reaction mixture was heated to 80 C and stirred overnight at 80 C. 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. C13H11BrFNO2; MW 312.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

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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Application of 2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, This compound has unique chemical properties. The synthetic route is as follows.

8-hydroxyjulolidine-9-carboxaldehyde0.91 g (4 mmol) was dissolved in 10 mL of ethanol,With two drops of hydrochloric acid2,2′-oxybis (ethylamine)0.22 mL (2 mmol) was slowly added to the solution. The mixture was stirred at room temperature for one day so that the mixed solution was well mixed. After the solvent was removed under reduced pressure, the crude product obtained was purified by column chromatography using a mixed solution of methylene chloride and methanol (MC: MeOH = 10: 1, v / v) to obtain 0.65 g of pure product. It was analyzed by 1 H-NMR, 13 C-NMR, ESI-MS, and EA to confirm that it had the structure of Formula 1, and the yield was 65%.

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

Reference:
Patent; Seoul National University of Science and TechnologyIndustry-AcademicCooperation Foundation; Kim, Chul; Song, Uhn Ju; Lee, Myung Mi; (17 pag.)KR2016/34631; (2016); A;,
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Electric Literature of 37895-73-1, These common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-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: A Schlenk flask was charged under argon with 1 equiv of dihaloarene, 0.2 equiv of CuI, 0.22 equiv of Cy3PHBF4, and 0.1 equiv of PdCl2(PPh3)2. The flask was closed, evacuated, and filled with argon (the procedure was repeated thrice), 8 mL of DMF (per millimole of dihaloarene), 4 equiv of triethylamine, and 3 equiv of lactone 1a or 1b were added with a syringe, and the mixture was heated for 8 h at 100C. The mixture was cooled and concentrated under reduced pressure, and the products were isolated by column chromatography using heptane-ethyl acetateas eluent.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghochikyan; Samvelyan; Galstyan; Gevorgyan; Vardanyan; Grigoryan; Langer; Russian Journal of Organic Chemistry; vol. 53; 12; (2017); p. 1833 – 1839; Zh. Org. Khim.; vol. 53; 12; (2017); p. 1797 – 1803,7;,
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Adding a certain compound to certain chemical reactions, such as: 41406-00-2, name is 3-Isopropoxyaniline, 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 41406-00-2, Computed Properties of C9H13NO

Example 3; General Procedure for Synthesis of Second Purine SNAr Products; The mono-SNAr product 14 (40 mg, 0.12 mmol) and 3-isopropoxyaniline (44 mul, 0.3 mmol) were added to a microwave vial, followed by the addition of isopropyl alcohol (IPA, 0.8 mL) and 4 drops of TFA. The mixture was irradiated in a microwave oven at 155 C. for 60 minutes to effect the desired reaction. After cooling the reaction vessel to room temperature, the volatiles were evaporated under reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography (RP-HPLC), eluting with a gradient of acetonitrile-water to provide the desired product 129, racemic-(2-exo,3-exo-)-N6-[3-(dimethylamino)carbonylbicyclo[2.2.1]hept-5-en-2-yl)]-N2-(3-isopropoxyphenyl)-1H-purine-2,6-diamine.

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Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; US2007/142402; (2007); A1;,
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Electric Literature of 150-78-7, 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. 150-78-7, name is 1,4-Dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 1-Methoxy-3,5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetate and cooled at 0 C. The product was isolated as filtrate upon paper filtration and waste succinimide as precipitate. The resulting filtrate were concentrated in vacuo to isolate 250 mg (yield: 85%) of 2b as colourless powder. To test the efficiency in large scale, the reaction was also performed for the mono-bromination of 1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product was isolated in 87% yield.[1] The milling apparatus was stopped and small portion of the sample was collected from the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.

The chemical industry reduces the impact on the environment during synthesis 1,4-Dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bose, Anima; Mal, Prasenjit; Tetrahedron Letters; vol. 55; 13; (2014); p. 2154 – 2156;,
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Reference of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine, This compound has unique chemical properties. The synthetic route is as follows.

1.3 Preparation of 2-Amino-4-chloro-6-di-(4-methoxybenzyl)amino-5-pyrimidine Carbaldehyde 2-Amino-4,6-dichloro-5-pyrimidine carbaldehyde (0.50 g; 2.60 mmol) was stirred in dry DCM (5 ml). Triethylamine (0.263 g; 2.60 mmol) and di(4-methoxybenzyl)amine (0.669 g; 2.60 mmol) were added and the reaction stirred at r.t for 1.25 h. the reaction was worked up by addition of further DCM (50 ml) and extraction with saturated sodium chloride solution (3*50 ml). The organic layer was washed with water (50 ml), dried (MgSO4) and evaporated yielding a yellow foam (0.957 g; 2.32 mmol; 89.2%).

The chemical industry reduces the impact on the environment during synthesis Bis(4-methoxybenzyl)amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cancer Research Campaign Technology Limited; US6677345; (2004); B1;,
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Synthetic Route of 592-55-2, 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. 592-55-2, name is 1-Bromo-2-ethoxyethane, This compound has unique chemical properties. The synthetic route is as follows.

Example 15Production of Compound A-7In a 100 ml four-neck flask, 8.567 g (0.0400 mol) of 3-hydroxynaphthalic anhydride, 48.0 g of dimethyl sulfoxide, and 10.081 g (0.0730 mol) of potassium carbonate were put and stirred, and the atmosphere in the system was replaced with nitrogen gas. Dropwise added was 11.233 g (0.0734 mol) of bromoethyl ethyl ether, and the resultant was stirred at 70 C. for 5 hours. In the reaction liquid, 12 ml of deionized water and 9.6 ml of 48% by weight aqueous sodium hydroxide solution were put, stirred at 50 C. for 2 hours, and thereafter ice-cooled, and 21.0 g of 35% by weight aqueous hydrochloric acid solution was put and stirred at 60 C. for 2 hours. The reaction liquid, 500 ml of methylene chloride, and 200 ml of deionized water were added and subjected to oil-water separation to yield the organic layer, which was washed three times with 200 ml of deionized water and thereafter concentrated, and the organic layer was concentrated and subjected to purification by silica gel chromatogram (developing solvent with a hexane-to-ethyl acetate volume ratio of 2 (hexane):3 (ethyl acetate)) to yield the compound A-7 which was a target as a pale yellow solid. Yield: 5.20 g (yield: 45.4%), purity: 98.3% by HPLC (column: Inertsil ODS-2 manufactured by GL Sciences Inc., 4.6 mm×250 mm, solvent: acetonitrile/water=7/3, L-7455 diode array detector manufactured by Hitachi, Ltd., detection wavelength: 230 nm). The measurement results of 1H-NMR by a deuterated dimethyl sulfoxide solvent are listed in Table 1-3.

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

Reference:
Patent; Murai, Toshihiko; Makabe, Yoshie; Fujita, Shohei; US2012/289697; (2012); A1;,
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Electric Literature of 17061-62-0,Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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 solution of N,N-bis(4-methoxybenzyl)amine (Intermediate EEl 1; 200 g, 775.19 mmol) in DCM (2.5 L) was added Et3N (336.17 mL, 2325.5 mmol), andthe reaction mixture was cooled to 0 C. Ethanesulfonyl chloride ( 95 mL,1007.75 mmol) was added in drop-wise manner followed by DMAP (19.0 g,155.03 mmol). The resulting reaction mixture was stirred at ambient temperaturefor 30 mm. The reaction was monitored by TLC and upon completion, themixture was diluted with H20 and the layers were separated and the aqueousphase was extracted with DCM (3 x 1.5 L). The combined organic layer waswashed with H20, brine, and dried over Na2504. The solvent was removed under reduced pressure to afford the cmde material which was purified by column chromatography over 5i02 gel (100-200 mesh), eluting with a gradient of 0-12% EtOAc in hexane affording the title compound (145 g, 5 3.4%) as a white fluffy solid.

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, its application will become more common.

Reference:
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); A1;,
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