Month: August 2021

Application of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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′,4′-dichloro-4-fluorobiphenyl-3-carbonitrile (173 mg, 0.650 mmol), 4-isopropoxyaniline (108 mg, 0.715 mmol), and KOtBu (154 mg, 1.375 mmol) in DMSO (4mL) was stirred at rt for 1.5h, The mixture was diluted with ethyl acetate, washed with H2O and brine, and then dried over Na2SO4. The solvent was removed and the product was purified by silica gel chromatography (eluting with hexane containing 0 to 8% ethyl acetate) followed by preparative HPLC (100 x 30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B =50:50 and ending with A:B =0: 100 [A = 10 mM NH4OAc in 5% aqueous acetonitrile; B = IO mM NH4OAc in 95% aqueous acetonitrile] over 20 min). This afforded 99 mg of 3′,4′-dichloro-4-(4-isopropoxyphenylamino)-biphenyl-3- carbonitrile which still contained some impurities according to the LC/MS but was used as such for next step. MS (ESI) m/z 397.1 (M+H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (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. 1535-73-5, name is 3-Trifluoromethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Trifluoromethoxyaniline

Example 6 : (+/-) 3-{f(3-trifluoromethoxyphenyl)amino1carbonyl)-1 ,2,2- trimethylcvclopentanecarboxylic acidA mixture of (+/-) camphoric acid anhydride (0.92 g, 5.05 mmol), anhydrous sodium acetate (0.5Og, 6.09 mmol) and 3-(trifluoromethoxy)aniline (1.015 g, 5.73 mmol) were heated in an oil bath at 140cC for 2 hours. The mixture was removed from the oil bath to cool sufficiently to add water (4 ml) and ethyl acetate (4ml). The mixture was stirred with heating to dissolve the solids before diluting with more ethyl acetate (20ml) and dilute hydrochloric acid (20 ml, 1M). The organic layer was taken and partially evaporated under vacuum to give a viscous oil. The oil was dissolved in ethyl acetate (6 ml) and then petroleum ether (6 ml, 40-60) added. The crystals that formed were collected and washed with more ethyl acetate/petroleum ether (1 :3, 6 ml) and dried under vacuum to give (+/-) 3-{[3-trifluoromethoxyphenyl)amino]carbonyl}- 1 ,2,2-trimethylcyclopentanecarboxylic acid as a white powder (0.97 g, 53percent yield) ; 1 H-NMR (400 MHz1 d6-DMSO) : 612.22 p.p.m. (s, 1 H), 10.01 (s, 1 H), 7.84 (S1 1 H)1 7.56 (m, 1 H)1 7.46 (t, J = 8 Hz, 1 H), 7.04 (m, 1 H), 2.91 (t, J = 9.4 Hz, 1 H), 2.49 (m, 1 H), 2.08 (m, 1 H)1 1.79 (m, 1 H), 1.46 (m, 1 H), 1.22 (s, 6H), 0.82 (S, 3H).

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 1535-73-5.

Reference:
Patent; MERLION PHARMACEUTICALS SA; MERLION PHARMACEUTICALS PTE LTD; WO2008/17840; (2008); 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 2062-98-8 as follows. category: ethers-buliding-blocks

To a solution of hydroxyacetone (7.4 g) and pyridine (8.1 ml) in ethyl acetate (100 ml), undecafluoro-(2-methyl-3-oxahexanoic acid)fluoride (10 g) was added dropwise at room temperature (25 C.). After stirring at room temperature for 2 hours, the reaction mixture was poured into diluted hydrochloric acid. After separation, the organic layer was washed with water and a saturated sodium chloride solution and dried with magnesium sulfate. The concentrated residue was purified by column chromatography (developing solvent: ethyl acetate/hexane), to obtain Compound B (10.2 g, 88%).1H NMR (CDCl3) delta 2.22 (s, 3H), 4.85 (d, J=16.2 Hz, 1H), 4.96 (d, J=16.2 Hz, 1H)19FNMR (CDCl3) delta -80.3 (1F), -81.8 (3F), -82.5 (3F), -86.7 (1F), -130.2 (2F), -132.8 (1F)

According to the analysis of related databases, 2062-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; US2009/18350; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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., Formula: C7H8BrNO

Roundbottom flask is charged with 5-bromo-2-methylaniline( 400.00 mg; 2.15 mmol; 1 .0 eg.), triethylamine ( 330.76 mL; 2.36 mmol; 1.1 eq.) and anhydrous dichloromethane (12 mL). Acetyl chloride ( 185.64 mg; 2.36 mmol; 1.1 eq.) is then added dropwise and reaction mixture is stirred at room temperature for 24h. After this time diethyl ether (24 mL) is added and mixture is washed with saturated aqueous solution of ammonium chloride (2×20 mL) and brine (2×20 mL). Organic layer is then dried over anhydrous Na2SO4 overnight. The second organic solvent is evaporated to afford N-(5- bromo-2-methylphenyl)acetamide (513.20 mg; yield 93.5 %; 89.3 % by UPLC) as brown solid.

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

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

A. 1H-Indazole-3-carboxylic acid (4-benzyloxy-phenyl)-amide DIEA (9.3 mL, 53.4 mmol) was added to a solution of 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol), indazole-3-carboxylic acid (2.89 g, 17.8 mmol) and HBTU (7.1 g, 18.7 mmol) in DMF (60 mL), and the resulting solution was stirred at ambient temperature for 24 hours. The solution was heated to 70 C for 4 hours, and then poured into a mixture of saturated aqueous sodium bicarbonate on ice. The product, an off white solid, 6.0 g, was collected by filtration, washed with water and used without further purification in the subsequent reaction. MS m/z344 (MH+).’H NMR (DMSO-d6) 8 5.11 (s, 2H), 7.02 (d, 2H), 7.26-7. 48 (m, 7H), 7.67 (d, 1 H), 7.75 (d, 2H), 7.81 (d, 1 H), 8. 24 (d, 1 H) and 10.24 (s, 1H).

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; JANSSEN PHARMACEUTICA N.V.; WO2005/84663; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 101-84-8, name is Diphenyl oxide, 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 101-84-8, Formula: C12H10O

EXAMPLE 1; A reactor is configured from a 1-liter Morton flask with a mechanical stirrer, thermometer, a 60 mL addition funnel, and a distillation column. The condenser from the distillation column is connected to a H2O trap. A small N2 purge is added to the line from the condenser to the H2O trap. The reactor is charged with AlCl3 and bromine. The addition funnel is charged with diphenyl oxide. The reactor is heated to 55 C. and the diphenyl oxide is added drop-wise supersurface to the bromine. The reactor is heated by a mantle. After all of the diphenyl oxide has been added, the addition funnel is replaced with a Br2 feed line. After several minutes of refluxing, the distillation of Br2 (containing HBr) is initiated. At the same time, the Br2 feed is initiated. As needed, the feed rate of the Br2 is adjusted so that the volume in the reactor remains fairly constant. After the distillation and concurrent replacement feed of Br2 are conducted for an hour, the liquid mixture is cooled to 55 C., some deionized H2O is added, and most of the Br2 is distilled off. When most of the Br2 is gone, more deionized water is added. The remaining Br2 is then distilled. The remaining mixture is cooled to 60 C., and a portion of an aqueous 25% NaOH solution is added to make the pH 13-14. The resultant mixture is filtered and washed well with deionized water. A sample is subjected to GC analysis and then is oven dried.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diphenyl oxide, and friends who are interested can also refer to it.

Reference:
Patent; ALBEMARLE CORPORATION; US2008/58558; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 592-55-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 592-55-2, name is 1-Bromo-2-ethoxyethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(A) A mixture of 4-bromo-3-methylphenol (10 g, 53.47 mmol), 1-bromo-2- ethoxyethane (10.62 g, 69.40 mmol) and K2CO3 (11.13 g, 79.95 mmol) in DMF (100 mL) was stirred overnight at 75 C. After cooling to rt, brine (250 mL) was added and the mixture was extracted with EtOAc (4 x 100 mL). The combined organic extracts were washed with brine (4 x 100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (5% EtOAc/petroleum ether afforded 1-bromo-4-(2-ethoxyethoxy)-2-methylbenzene (12.25 g, 88 %) as light yellow oil which was used directly.

The synthetic route of 1-Bromo-2-ethoxyethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; KUO, Gee-Hong; PLAYER, Mark R.; YANG, Shyh-Ming; ZHANG, Yue-Mie; HUANG, Hui; (260 pag.)WO2016/57731; (2016); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. Computed Properties of C8H8Br2O2

Add to the dry three-necked flask with a magnetic rotor 1,3-dibromo-4,6-dimethoxybenzene (3.0515 g, 10 mmol, 97%, 1.0 eq),4-biphenylboronic acid (4.4449 g, 22 mmol, 98%, 2.2 equivalents),palladium acetate (0.0674g, 0.3mmol,0.03 equivalents) and the ligand S-Phos (0.2513 g, 0.6 mmol, 98%, 0.06 equivalents).Nitrogen gas was distilled off three times, and then an aqueous solution (20 mL) of 1,4-dioxane (60 mL) and potassium carbonate (6.9100 g, 50 mmol, 5.0 eq. The three vials were then placed in a 110 C oil bath. After stirring for 24 hours, the reaction was monitored by thin layer chromatography. After cooling to room temperature, the organic phase was separated and aqueous was extracted with ethyl acetate (30mL×2).The organic phases were combined, dried over anhydrous sodium sulfate, filtered and evaporated.The crude product was separated and purified by flash column chromatography on silica gel (eluent: petroleum ether / ethyl acetate = 50/1) to give A5, white solid 4.4216g, 99% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24988-36-1, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Li Guijie; Dai Jianxin; Chen Shaohai; Feng Qi; (28 pag.)CN110183476; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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: Diester1 (1mmol) and the appropriate diamine2-6 (1mmol) were dissolved in dry methanol (50mL) and sodium methoxide (2mmol) was added. A mixture was stirring for 72hat room temperature. After completion of the reaction (controlled by TLC), the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography (1-5% MeOH in CH2Cl2). All the macrocyclic products obtained in this way are colourless solids, stable to air.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pikus, Grzegorz; Jurczak, Janusz; Tetrahedron; vol. 72; 16; (2016); p. 1928 – 1932;,
Ether – Wikipedia,
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Application of 261762-35-0, These common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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.

In a 50 mL round-bottom flask, introduce 1 g (4.48 mmol) of 5-bromo-2,3-difluoroanisole in 25 mL of dioxane then add 1.708 g (6.73 mmol) of bis(pinacolato)diboron, 1.320 g (13.45 mmol) of potassium acetate and 0.183 g (0.224 mmol) of bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The reaction mixture is stirred at 80 C. overnight. After returning to room temperature, the reaction is hydrolyzed by slow addition of water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 95:5) to afford 197 mg (15%) of intermediate 13 as a yellow solid. (0484) LCMS (EI, m/z): (M+1) 271.08 (0485) 1H NMR: dH ppm (400 MHz, DMSO): 7.13-7.17 (2H, m, CHarom), 3.90 (3H, m, CH3), 1.30 (12H, m, CH3).

The synthetic route of 261762-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KALOUN, El Bachir; GRISONI, Serge; GOMES, Bruno; SCHMITT, Philippe; (43 pag.)US2017/281622; (2017); A1;,
Ether – Wikipedia,
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