Tag: M.W=100-200

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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2-ethoxyethane

Example 38Synthesis of (Z)-2-ethoxy-3-[2-(2-ethoxyethoxy)-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylic acid a-Methyl 3-(2-ethoxyethoxy)-4-iodobenzoate:3.15 g (20 mmol) of 2-bromoethyl ethyl ether and 3.4 g (24.6 mmol) of potassium carbonate are added to a solution of 5.7 g (20 mmol) of methyl 3-hydroxy-4-iodobenzoate (prepared according to Example 19d) in 50 mL of methyl ethyl ketone. The reaction mixture is heated at 80 C. for 12 hours. The reaction is stopped by addition of 50 mL of water and extraction with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 5.93 g (83%) of methyl 3-(2-ethoxyethoxy)-4-iodobenzoate are obtained in the form of a colorless oil.

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; GALDERMA RESEARCH & DEVELOPMENT; US2009/12129; (2009); A1;,
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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;,
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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;,
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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;,
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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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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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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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Trifluoromethoxy)aniline

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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Application of 19500-02-8, 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 19500-02-8 as follows.

Step 3: synthesis of (2-amino-4-methoxy-3-methylphenyl)(methyl)ketone (4). A solution Of BCl3 (1.0 M, 200 mL, 200 mmol) in CH2Cl2 was slowly added under nitrogen to a solution of 3-methoxy-2-methylaniline (26.0 g, 190 mmol) in xylene (400 mL). The temperature was monitored during the addition and was kept below 100C. The reaction mixture was stirred at 5°C for 0.5 h. Then, dry acetonitrile (13 mL, 246 mmol) was added at 5°C. After 0.5 h at 5°C, the solution was transferred into a dropping funnel and slowly added at 5°C to a suspension OfAlCl3 (26.7 g, 200 mmol) in CH2Cl2 (150 mL). After 45 min at 5°C, the reaction mixture was heated at 700C under a nitrogen stream. After evaporation Of CH2Cl2, the temperature of the reaction mixture reached 65°C. After 12 h at 65°C, the reaction mixture was cooled at 00C, poured onto ice (300 g), and slowly heated to reflux for 7h. After 2 days at room temperature, 6 N NaOH (50 mL) was added. The pH of the resulting solution was 2-3. The xylene layer was decanted. The organic layer was extracted with CH2Cl2. The xylene and CH2Cl2 layers were combined, successively washed with water, IN NaOH, and brine, dried (Na2SO4) and evaporated. The residue was triturated in diisopropyl ether at O0C, filtered off and washed with diisopropylether to give 13.6 g (40 percent) of the title product as a yellowish solid: m/z = 180 (M+H)+.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96002; (2008); A1;,
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Electric Literature of 1535-73-5, 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 1535-73-5 as follows.

General procedure: An equimolar mixture of trifluoromethoxyaniline 1 or 2 (5.65 mmol) and the corresponding activated enol ether 3a-h was heated under reflux for 2-120 min (TLC detection). If necessary, methanol or ethanol was used as solvent. Once the reaction was complete, it was cooled to room temperature and the solids formed were separated by suction, washed with hexanes and dried to give enamines 4-5a-h. Isolated enamines 4-5a-h were characterized and used in the subsequent steps.

According to the analysis of related databases, 1535-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Plevova, Kristina; Briestenska, Katarina; Colobert, Francoise; Mistrikova, Jela; Milata, Viktor; Leroux, Frederic R.; Tetrahedron Letters; vol. 56; 36; (2015); p. 5112 – 5115;,
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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. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Phenoxyethylamine

General procedure: A solution of 2-phenoxyethylamine (1.31 mL, 10 mmol) in methanol (10 mL) was added to a solution of triethylamine(Et3N) (2.76 mL, 20 mmol) in methanol (10 mL) at 0 C. A solution of 2-chloropyridine (3.80 mL, 40 mmol) in methanol(10 mL) was then added at 0 C under N2. After being stirred for 30 min, the reaction mixture was heated to 25 C and stirred for 3 days. Then, the solvent was evaporated under reduced pressure to afford a yellow solid L1 washed with methanol and dried under vacuum.

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 1758-46-9.

Reference:
Article; Wang, Jun; Liu, Jinyi; Chen, Liduo; Lan, Tianyu; Wang, Libo; Transition Metal Chemistry; vol. 44; 7; (2019); p. 681 – 688;,
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