Tag: M.W=100-200

Some common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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. 454-90-0

1. Preparation of 2-Propylthio-3-(trifluoromethyl)-anisole A solution of 30 mL (milliliter) (208 mmol) (millimole) of 3-(trifluoromethyl)anisole in 500 mL of dry tetrahydrofuran was cooled to -70 C. under a nitrogen blanket and 100 mL (250 mmol) of 2.5M butyl lithium in hexane was added slowly with stirring and cooling. The reddish solution was stirred at -70 C. for 1 hour and then 42 mL (270 mmol) of dipropyl disulfide was added slowly with stirring and cooling. The resulting mixture was allowed to warm to ambient temperature over an 18-hour period. The mixture was quenched with 250 mL of saturated aqueous ammonium chloride. The organic phase was recovered, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The yellow oil residue was fractionally distilled in a Vigreux column at 0.2 mm Hg (millimeters of mercury) (27 Pascals) to obtain 37 g (gram) (71 percent of theory) of a clear liquid product fraction boiling at 92 C.

The chemical industry reduces the impact on the environment during synthesis 3-(Trifluoromethyl)anisole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dow AgroSciences LLC; US5858924; (1999); A;,
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A common compound: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1535-73-5

General procedure: A solution of cyanic bromide [Caution, highly toxic] (2 equiv) in diethyl ether (10 mL) was added dropwise to a solution of the appropriately substituted aniline (1 equiv) in diethyl ether (10 mL) at 0 ¡ãC. After complete addition the mixture was warmed to ambient temperature and stirred 1?20 h, which was followed by TLC. Solids were filtrated and washed with ether. The filtrate was washed with 1 M HCl (25 mL) followed by brine (25 mL). The organic layer was collected, dried over anhydrous MgSO4, filtrated and evaporated to dryness under reduced pressure. 5.1.33 N-(3-(Trifluoromethoxy)phenyl)cyanamide (24i) The reaction of 3-(trifluoromethoxy)aniline (23i) (1.780 g, 10.05 mmol) according to procedure A yielded, after purification over silica with ethyl acetate/petroleum ether (60-80) (25/75, v/v), the title compound as a white solid (583 mg, 2.88 mmol, 29percent); Rf 0.43 (ethyl acetate/petroleum ether (60-80), 25/75, v/v). 1H NMR (CDCl3) delta 7.39-7.32 (m, 2H, HAryl), 6.99-6.93 (m, 2H, HAryl), 6.88 (s, 1H, NH). 13C NMR (CDCl3) delta 150.34 (Ar-O), 139.03 (Ar-N), 131.15 (Ar), 120.47 (q, CF3, JCF = 258.08 Hz), 115.84 (Ar), 113.82 (Ar), 111.06 (NCN), 108.58 (Ar).

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, 1535-73-5, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Klein, Pieter J.; Christiaans, Johannes A.M.; Metaxas, Athanasios; Schuit, Robert C.; Lammertsma, Adriaan A.; Van Berckel, Bart N.M.; Windhorst, Albert D.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1189 – 1206;,
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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. 946-80-5, name is Benzyl Phenyl Ether, This compound has unique chemical properties. The synthetic route is as follows., 946-80-5

A. 4-Benzyloxybenzenesulfonyl chloride To 0.87 g of dimethylformamide, at 0 C. under an atmosphere of nitrogen, was added 1.61 g of sulfuryl chloride. The mixture was stirred for 15 min and treated with 2.00 g of benzyl phenyl ether. The mixture was then heated at 100 C. for 1.5 h, cooled to about 40 C., poured onto ice, extracted with CH2 Cl2, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by low pressure silica gel chromatography using 10% ethyl acetate in hexane as eluent to provide 0.78 g of the title product as a white solid. TLC: Rf=0.46, 10% ethyl acetate in hexane. (1 H)-NMR (CDCl3) consistent with structure.

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:
Patent; Vertex Pharmaceuticals, Incorporated; US5783701; (1998); A;,
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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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 6346-09-4

Intermediate 145: 6-Chloro-N4-(4,4-diethoxybutyl>N2-methylpyridine-2,4- dicarboxamide (0902) (0903) To a solution of 2-chloro-6-(methylcarbamoyl)isonicotinic acid (2 g, 8.85 mmol) and HATU (3.70 g, 9.74 mmol) in DMF (20 mL) was added DIPEA (3.09 mL, 17.71 mmol) followed by 4,4- diethoxybutan-l-amine (1.68 mL, 9.74 mmol). The resulting solution was stirred at rt for 16 h. Water (60 mL) and EtOAc (60 mL) were added and the layers separated. The aqueous layer was further extracted with ethyl acetate (2 x 30 mL). The combined organics were back-extracted with water (2 x 30 mL) and sat. aqueous LiCI (30 mL) and then dried (Na2S04), filtered and concentrated in vacuo to give a dark oil. This was re-dissolved in DCM and directly applied to the top of a 100 g SNAP silica cartridge and purified by SP4 flash column chromatography. The column was eluted with a gradient of 30-70% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product, 6-chloro-N4-(4,4-diethoxybutyl)-N2-methylpyridine-2,4-dicarboxamide (2.39 g, 6.68 mmol, 75 % yield) as a yellow oil. (0904) LCMS (2 min High pH): Rt = 0.92 min, [MH]- = 356.2.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
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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. 767-91-9 name is 2′-Methoxyphenyl acetylene, 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. 767-91-9

5b) 2-isopropoxy-5-(2-methoxy-phenylethynyl)-benzoic acid methyl ester 5-lodo-2-isopropoxy-benzoic acid methyl ester (500 mg), 2-methoxy-phenyl acetylene (0.40 ml), palladium dichlorobis(triphenylphosphine) (12 mg) and Cul (6 mg) in diethylamine (10 ml) were stirred at 60C for 12 hours. The reaction mixture was concentrated and extracted with ethylacetate / water. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The title compound was obtained in 64 % yield after flash chromatography. 1H-NMR (CDCl3): 7.97 d (J = 2.3 Hz, 1 H); 7.59 dd (J = 2.3 Hz / 8.7 Hz, 1 H); 7.47 dd (J = 7.5 Hz / 1.7 Hz, 1 H); 7.30 m (1 H); 6.96 m (3H); 4.62 m (1 H); 3.91 s (3H); 3.88 s (3H); 1.38 d (J = 8.7 Hz, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2′-Methoxyphenyl acetylene, and friends who are interested can also refer to it.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1985612; (2008); A1;,
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A common compound: 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 60792-79-2

[0329] In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min. A solution containing Boc20 (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2C12 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2- aminoethoxy)ethylcarbamate (850 mg, 74%).

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, 60792-79-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; BEMIS, Jean E.; VU, Chi B.; MILNE, Jill C.; JIROUSEK, Michael R.; DONOVAN, Joanne; WO2014/107730; (2014); A2;,
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366-99-4, A common compound: 366-99-4, name is 3-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 4; Parallel Synthetic Method B, for Library II Compounds; Fifty mL (13.5 mmol) of the prepared (4,6-dichloro-[1,3,5]triazin-2-yl)-(3-fluoro-4-methoxy-phenyl) amine solution was divided equally (2 mL or 0.54 mmol each) among 25 barcoded, 40 mL scintillation vials. Individual solutions of each R2NHR (where R2 amine indicates Monomer 2 in Table 2, 0.542 mmol) and DIEA (77 mg /104 muL, 0.596 mmol) in 0.5 mL of CH3CN were prepared and added to the correspondingly labeled 40 mL vials. The resulting solutions were shaken on the J-KEM block overnight at room temperature and then placed in a freezer (about -14 ¡ã C.) without purification until the next reaction.; Example 5; Parallel Synthetic Method C, for Library III Compounds; In an oven-dried round bottom flask, a solution of cyanuric chloride (5.0 g, 27.1 mmol) in 1,4-dioxane (40 mL) was cooled to freezing in a CH3CN/dry ice bath. To this frozen solution was added 40 mL of CH3CN, followed by DIEA (3.85 g/5.19 mL, 29.8 mmol). A solution of 3-fluoro-p-anisidine (3.83 g, 27.1 mmol) in 10 mL of CH3CN was then added slowly via syringe. The reaction mixture was stirred at about -20¡ã C. for about 1h and allowed to warm to room temperature over 1 h. The resulting 2-amino-4,6-dichlorotriazine solution was carried to the next step without 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-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
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101-84-8, The chemical industry reduces the impact on the environment during synthesis 101-84-8, name is Diphenyl oxide, I believe this compound will play a more active role in future production and life.

Example 1; Decabromodiphenyl ether – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 % w/w) ; bromine, 475 g; AlCl3,4.3 g; and ceramic beads (1.5-3.5 mm diameter), 814 g-A solution of diphenyl oxide (42.5 g, ) in 20 ml of solvent mixture was dropped into the flask during 70 minutes with stirring while keeping the temperature at 7- 13 C . The reaction mixture was refluxed for 4.5 hours, the flask was cooled and 55 ml of water was carefully added to destroy the catalyst. Excess bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 99.4 % decabromodiphenyl ether and 0.1 % nonabromodiphenyl ether (in the Examples sometimes abbreviated “Deca” and “Nona”, respectively). Particle size 7.1 microns (dg0) .; Example 2 (comparative); Decabromodiphenyl ether – Bromination without milling in a mixed solvent.; The procedure of Experiment 1 was repeated without the ceramic beads present. The product consisted of 94.1 % Deca and 5.8 % Nona. Particle size 98 microns (d90).; Example 3; Decabromodiphenyl ether- increasing the crystal size of milled Deca in a simulated reaction mixture after bromination and destruction of the catalyst.; The product of Example 1, having a particle size of 7.1 microns (dgo) and an assay of 99.4 %, was charged to a 1 liter flask followed by 440 g of solvent mixture (DCM 20 %, CBM 40 %, and DBM 40 %); 4.3 g AlCl3, 50 g of bromine and 50 ml of water to destroy the catalyst. The mixture was refluxed for 5.3 hours, cooled and bleached with bisulfite. The product was filtered, washed with water and dried. The particle size v/as 28.8 microns (dgo), had an assay of 99.7 % and was easily filtered.; Example 7; Decabromodiphenyl ether – Bromination of pre-milled Deca precursor; To a 2 liter jacketed reaction vessel equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 500 g of milled Deca (content 97.3 %, particle size 3.8 microns (d90) ) , 1945 g of solvent mixture, 444 g bromine and 22 g AICI3. The mixture was heated at reflux for 3.5 hours. Water, 260 ml, was added and the excess bromine was bleached with sodium bisulfite solution. To the thick slurry was added 150 ml of water. The mixture was filtered and the dried solid comprised 99.6 % Deca with particle size 38.5 microns (dgo).; Example 8; Decabromodiphenyl ether- Bromination of pre-milled Deca precursor on an industrial scale; A reactor vessel of 16 cubic meters capacity was charged with 7500 liters of solvent consisting of 12.6 % dichloromethane, 32.5 % bromochloromethane and 54.9 % dibromomethane . Aluminum chloride, 150 kg, 8 tons of pre- milled Deca (Deca content 97.9 % with particle size 14 microns (dg0) ) and 1000 kg of bromine were added. The mixture was heated at reflux for 8 hours and was then bleached with 1340 liters of 38 % sodium bisulfite solution. The upper aqueous solution was decanted and the mixture was washed with two 1200 liters portions of water. Sodium hydroxide, 20 %, was added to neutralize the mixture which was then centrifuged. The product was dried and was found to contain 99.3 % Deca with particle size 42 microns (d90).; Example 9; Decabromodiphenyl ethane – Simultaneous bromination and milling in a mixed solvent; To a 1 liter round bottomed flask equipped with a mechanical stirrer, a dropping funnel, a thermocouple and a reflux condenser was added 520 g of solvent mixture (DCM 6 %, CBM 20 %, and DBM 74 % ) ; bromine, 539 g; AlCl3, 9 g; and ceramic beads (1.5-3.5 mm diameter), 840 g.A 55 % solution of diphenyl ethane in DCM (91.1 g, ) was dropped into the flask during 30 minutes with stirring while keeping the temperature at 21-26 0C. The reaction mixture was refluxed for 6.7 hours, and 120 ml of water was carefully added to destroy the catalyst. Bromine was bleached with sodium bisulfite solution, the aqueous phase was separated and the organic phase was washed with water and was neutralized with 20 % NaOH. The product mixture was passed through a sieve to remove the ceramic beads and the mixture was filtered, washed with water and dried. The product comprised 91.4 % decabromodiphenyl ethane and 7.8 % nonabromodiphenyl ethane. Particle size was 6.1 microns (d90).; Example 10 (comparative); Decabromodiphenyl ethane – Bromination without milling in a mixed solvent.; The procedure of Example 9 was repeated without the ceramic beads present. The product comprised 80.6 % decabromodiphenyl ethane and 18.6 % nonabromodiphenyl ethane. Particle size 22 .microns (dgo).

The chemical industry reduces the impact on the environment during synthesis Diphenyl oxide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BROMINE COMPOUNDS LTD.; WO2008/26215; (2008); A2;,
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Adding a certain compound to certain chemical reactions, such as: 349-55-3, name is 3-Methoxy-5-(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 349-55-3, 349-55-3

EXAMPLE 124 4-(3-Methoxy-5-trifluoromethylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 3-methoxy-5-trifluoromethylaniline (55 mg, 0.290 mmol) similar to Example 117 and isolated as a yellow solid (27 mg, 34%). 1H NMR (CDCl3): 9.65-9.64 (m, 1H), 8.75-8.70 (m, 2H), 7.46-7.41 (m, 2H), 7.36 (s, 1H), 7.31 (s, 1H), 7.00 (s, 1H), 6.93 (s, 1H), 3.91 (s, 3H).

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-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
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134364-69-5, 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. 134364-69-5, name is 2,3-Difluoroanisole, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of l,2-difluoro-3-methoxybenzene (3.0 g, 21 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise tert-butyllithium (19 mL, 25 mmol, 1.3 M in n-pentane). The mixture was stirred at this temperature for 30 minutes, then NN- dimethylformamide (6.1 g, 83 mmol) was added dropwise at -70 C. The reaction was stirred at – 70 C for another 2 hours. On completion, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give compound B-168 (4.0 g, crude) as a yellow solid. LCMS (B): tR=0.661 min., (ES+) m/z (M+H)+ =173.1.

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:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
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