Tag: M.W=100-200

Application of 93-04-9, These common heterocyclic compound, 93-04-9, name is 2-Methoxynaphthalene, 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.

EXAMPLE 1 The following is a procedure for preparing 2-methoxy-6-ethylnaphthalene by the transethylation of 2-methoxynaphthalene. To a 250 ml., 3-neck, round-bottom flask equipped with a magnetic stirrer and a sparge tube were added 70 g of mixed diethylbenzenes obtained from the Aldrich Chemical Company, Milwaukee, Wis. After cooling the reaction mixture with an ice bath, hydrogen chloride gas was added for three minutes and thereupon 14.48 grams of aluminum chloride were slowly added. Hydrogen chloride gas was again added for three minutes. The reaction flask was then placed in a hot water bath to raise the temperature of the reaction mixture to 85-90 C. At this point ethylene gas was sparged into the reaction mixture until the level of tetraethylbenzene in the reaction mixture was maximized. The composition of the mixture was monitored by gas chromatography. After the ethylene addition was stopped, the reaction mixture was stirred for an additional 30 minutes at 90 C. To the above reaction mixture at 15 C. was added a mixture of 29.02 grams of 2-methoxynaphthalene dissolved in 50 ml of dichloromethane. The reaction mixture was permitted to warm to room temperature and after 900 minutes it was heated to 32 C. using a water bath. After 15 hours total reaction time the yield of 2-methoxy-6-ethylnaphthalene was 71.5% as measured by gas chromatography. This example shows the high yield of 2-methoxy-6-ethylnaphthalene that can be achieved by the method of this invention.

Statistics shows that 2-Methoxynaphthalene is playing an increasingly important role. we look forward to future research findings about 93-04-9.

Reference:
Patent; Amoco Corporation; US5235115; (1993); A;,
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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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 111-95-5

Into a 10-mL vial, was placed a solution of bis(2-methoxyethyl)amine (285.6 mg, 2.15 mmol, 3.00 equiv) in N,N-dimethylformamide (3 mL), and N,N-diisopropylethylamine (277 mg, 2.14 mmol, 2.99 equiv). This was followed by the addition of a solution of N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide (300 mg, 0.72 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL). The resulting solution was stirred for 48 h at 80 C. in an oil bath. The reaction progress was monitored by LCMS. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3*50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2*70 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5?1). The product was obtained as 270 mg (71%) of a yellow to green oil.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ardelyx, Inc.; Lewis, Jason G.; Jacobs, Jeffrey W.; Reich, Nicholas; Leadbetter, Michael R.; Bell, Noah; Chang, Han-Ting; Chen, Tao; Navre, Marc; Charmot, Dominique; Carreras, Christopher; Labonte, Eric; (323 pag.)US9301951; (2016); B2;,
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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.

General procedure: To a stirred solution of 22 (30 mg, 0.081 mmol) in DMF (3 mL) were added K2CO3 (170 mg, 1.20 mmol), NaI (180 mg, 1.20 mmol) and 2-bromoethyl methyl ether (75 muL, 0.81 mmol), and stirred at 100 C under an Ar atmosphere. After 3 h with stirring, the reaction mixture was evaporated in vacuo. The resulting mixture was basified (pH 9) with saturated NaHCO3 aqueous solution and extracted with CHCl3 three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by preparative TLC (CHCl3/MeOH = 10:1) to give 26 (27 mg, 77%) as a colorless oil.

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:
Article; Nemoto, Toru; Ida, Yoshihiro; Iihara, Yusuke; Nakajima, Ryo; Hirayama, Shigeto; Iwai, Takashi; Fujii, Hideaki; Nagase, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7628 – 7647;,
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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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., SDS of cas: 102-52-3

Concentrated hydrochloric acid (14.5 ml, 87 mmol) was added dropwise to the stirred mixture of 2-iodophenylhydrazine (14 g, 60 mmol) and malondialdehyde bis(dimethyl acetal) (12 g, 72 mmol) at 0 C. After the addition completed, the reaction mixture was stirred for 2 h at room temperature, and water (20 ml) was added. Then, the reaction mixture was neutralized with NaOH solution (1 M). The solution was extracted with ethyl acetate (3 * 30 ml). The organic phases were combined, and dried over anhydrous MgSO4. After the solvent was removed under reduced pressure, red oil was obtained. Yield: 11.8 g (73%). 1H NMR: delta 6.49 (t, J = 2.1 Hz, 1H, H4 of pyrazole), 7.16 (dt, J = 2.0 Hz, J = 7.9 Hz, 1H), 7.41-7.48 (m, 2H), 7.98 (dd, J = 0.9 Hz, J = 8.0 Hz, 1H) (C6H4), 7.73 (d, J = 2.3 Hz, 1H), 7.77 (d, J = 1.4 Hz, 1H) (H3 and H5 of pyrazole) ppm. 13C NMR: delta 94.4, 106.6, 128.2, 129.0, 130.2, 131.1, 140.1, 140.8, 143.4 (C6H4 and carbons of pyrazole) ppm. HRMS-ESI (m/z): 292.9547 (Calc. for C9H7IN2Na: 292.9552, [M + Na]+, 100%).

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; Cheng, Cai-Hong; Chen, Dan-Feng; Song, Hai-Bin; Tang, Liang-Fu; Journal of Organometallic Chemistry; vol. 726; (2013); p. 1 – 8;,
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Adding a certain compound to certain chemical reactions, such as: 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, 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 393-15-7, Recommanded Product: 393-15-7

A. & B. 4-Methoxy-3-trifluoromethylaniline (46.54 g, 0.243 mole), concentrated HCl (87 ml) and water (122 ml) were stirred together and cooled to 0. A solution of sodium nitrite (17.07 g, 0.247 mole) in water (98 ml) was added dropwise, keeping the temperature at 0-5. After the addition was complete, the reaction was stirred at 0-5 for 0.5 hours. Then, all at once, 2-furaldehyde (23.42 g, 0.244 mole) and a solution of copper (II) chloride hydrate (5.60 g) in water (37 ml) were added. The ice bath was allowed to melt gradually as the reaction stirred for 2 days. An oil which had separated was extracted into ethyl acetate (400 ml). The ethyl acetate was washed with water (2*300 ml), dried over MgSO4, treated with Darco and filtered. The solvent was evaporated in vacuo leaving behind a dark oil (55.17 g). The sample required purification by liquid chromatography (solvent: hexane:ethyl acetate 3:1). The yield of purified sample was 16.56 g (25% yield) of 5-(4-methoxy-3-trifluoromethylphenyl)-2-furancarboxaldehyde (B). The IR and NMR confirmed the structure of B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-3-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Norwich Eaton Pharmaceuticals, Inc.; US4882354; (1989); A;,
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Reference of 4393-09-3, 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. 4393-09-3 name is (2,3-Dimethoxyphenyl)methanamine, 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 suspension of ethyl 4-trifluoromethoxybenzimidate hydrochloride salt (8) (1 equiv) in ethanol (0.25 M) was added the appropriate amine (0.9 equiv). Triethylamine (3 equiv) was added and the resulting reaction mixture stirred at ambient temperature for 16 h. The reaction mixture was then concentrated and the crude product purified by flash chromatography on silica.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2,3-Dimethoxyphenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Beinat, Corinne; Banister, Samuel D.; Hoban, Jane; Tsanaktsidis, John; Metaxas, Athanasios; Windhorst, Albert D.; Kassiou, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 24; 3; (2014); p. 828 – 830;,
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Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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 1535-75-7, Safety of 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¡Á25mL). 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.

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-(Trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

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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Related Products of 10103-06-7, A common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

(a) 1-(6,7-Dimethoxy-naphthalen-2-yl)-heptan-1-one Aluminium chloride (2.66 g) was added to a solution of: heptanoylchloride (3.1 ml) and 2,3-dimethoxynaphthalene (3.76 g) in methylene chloride (50 ml) at 0 C. The reaction mixture was stirred at room temperature overnight and then worked up as described in example 3(a). The crude product was recrystallized from ethanol. Yield: 2.8 g, melting point 77-78 C. 1H-NMR (DMSO-d6, 400 MHz): 8.49 (s,1H), 7.81 (s,2H), 7.51 (1H); 7.18 (s,1H), 3.92 (s,3H), 3.91 (s,3H), 3.07 (t,2H, J=8 Hz), 1.61-1.68 (m,2H), 1.29-1.37 (m,8H), 0.87 (t,3H, J=8 Hz).

The synthetic route of 10103-06-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
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Reference of 2688-84-8,Some common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, molecular formula is C12H11NO, 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-phenoxyaniline (25.0, 0.135 mol) and 30 ml of hydrochloric acid were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 C and stirred for 1 hour.75 ml of an aqueous solution of sodium nitrite (11.2 g, 0.162 mol) was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour.When the aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the temperature of the reaction solution was prevented from exceeding 5 and dropping.The mixture was stirred at room temperature for 5 hours and washed with an aqueous sodium thiosulfate solution after completion of the reaction, followed by extraction with ethyl acetate and water.The organic layer was separated and concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate 5-a (22.6 g, 56.5%).

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Co., Ltd.; Che Chunxu; Po Xipei; Po Shangyu; Shen Youna; Jin Xida; (130 pag.)CN107207454; (2017); A;,
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Application of 24332-20-5, These common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, 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.

Example 9 A flask was charged with methoxyacetaldehyde dimethylacetal (1.2 equiv.), trifluoroacetic acid (1.3 equiv.), and water (equal volume to TFA), and the mixture was stirred at 50 C for 10 min. The reaction mixture was then removed from the heating bath and TEA (1.3 equiv.) was added followed by a solution of 3-(N-Boc-aminomethyl)-azetidine (1 equiv.) in EtOH and DCM, and then NaBH(OAc)3 (3 equiv.). The reaction was stirred for 12 hrs at 20 C. The reaction mixture was extracted and distilled to remove some ethanol. To the organic layer was added 5M HCl in iPrOH (7 equiv.) at 50 C. TBME was added at 48 C over 45 min, and cooled to 20 C over 60 min. The reaction stirred for another 60 min, filtered, and the filter cake was washed with TBME. The organic layer was dried to provide 1 -(2-methoxyethyl)-3-(methylamino)-azetidine dihydrochloride.

Statistics shows that 1,1,2-Trimethoxyethane is playing an increasingly important role. we look forward to future research findings about 24332-20-5.

Reference:
Patent; SATORI PHARMACEUTICALS, INC.; BRONK, Brian, Scott; AUSTIN, Wesley, Francis; CREASER, Steffen, Phillip; FULLER, Nathan, Oliver; HUBBS, Jed, Lee; SHEN, Ruichao; WO2013/36665; (2013); A1;,
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