Tag: M.W=100-200

Electric Literature of 13468-02-5,Some common heterocyclic compound, 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, molecular formula is C10H15NO, 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.

The oil XI 132g (0.8mol), 30% concentrated hydrochloric acid 195g (1.6mol) was dissolved in 400ml of water with stirring, at -10 temperature or less, 40% formaldehyde was slowly added dropwise a solution of 40g (0.8mol) reaction was continued for 2 hours; TLC monitoring completion of the reaction, the pH was adjusted to 8 with sodium carbonate to 9, and extracted twice with dichloromethane, organic phases were combined and concentrated to give an oil, 300ml ethyl acetate was added to dissolve,Was added dropwise 30% HCl / ethanol, precipitated crystals were filtered to give 112.7g compound XII, a yield of 56.3%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Dimethyl-2-phenoxyethanamine, its application will become more common.

Reference:
Patent; Weihai Di Su Pharmaceutical Co., Ltd.; Wu, Ronggui; Jiang, Kai; An, Donghua; Cui, Yangyang; Men, Lianbin; (7 pag.)CN105985257; (2016); A;,
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Synthetic Route of 1579-40-4, 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 1579-40-4 as follows.

An H-shaped reactor with two reaction chambers was purged with argon. A stirring bar (1.0 mm × 0.4 mm) was then located in each chamber of the reactor. Sulfuric acid (0.8 mL, 1.47 g, 15.0 mmol) was placed at the bottom of one chamber (chamber 1) of the reactor, and Galden HT-135 (1.0 mL) was slowly added to chamber 1 using a syringe. Subsequently, ammonium formate (443 mg, 7.0 mmol) was added, which formed a third layer in chamber 1. A solution of di-p-tolyl ether (13, 198.6 mg, 1.0 mmol), Pd(OAc)2 (5.5 mg, 2.5 mol%), and K2S2O8 (541.0 mg, 2.0 mmol) in trifluoroacetic acid (2.5 mL) was placed in the other chamber (chamber 2) of the reactor. Rubber septa were fitted to the reactor, and a needle equipped with a balloon was then pricked into the septum of chamber 2. The air in the reactor was withdrawn using a syringe until the balloon was completely flattened. The reactor was the heated in an oil bath at 45 C for 5 h under slow stirring, with care taken not to mix the layers in chamber 1, then allowed to cool to 25 C. The mixture in chamber 2 was transferred to an Erlenmeyer flask containing water using dichloromethane (DCM). The organic layer was separated, and the aqueous layer was extracted with DCM. The combined organic layers were washed with brine then dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica-gel column chromatography using hexane/chloroform (1/4) as the eluent to afford desired product, 2,7-dimethylxanthen-9-one (14, 178.8 mg, 80%) as a white solid. 2,7-Dimethylxanthen-9-one (14) [S14] OCO2MeO S11 1H-NMR (400 MHz, CDCl3): delta 8.12 (2H, d, J = 0.9 Hz, ArH), 7.53 (2H, dd, J = 8.5, 2.1 Hz, ArH), 7.39 (2H, d, J = 8.7 Hz, ArH), 2.47 (6H, s, CH3); 13C-NMR (100 MHz, CDCl3): delta 177.36, 154.42, 135.94, 133.48, 126.02, 121.43, 117.75, 20.89.

According to the analysis of related databases, 1579-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adachi, Yusuke; Matsubara, Hiroshi; Journal of Fluorine Chemistry; vol. 216; (2018); p. 89 – 95;,
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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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6851-80-5

General procedure: To a mixture of the corresponding secondary amines 14A-F (0.6 mmol), anhydrous K2CO3 (89.7 mg, 0.65 mmol) and KI (8.6 mg, 0.052 mmol) in anhydrous CH3CN (12 ml) were added the appropriate intermediates 10-13 (0.5 mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water (40 mL) and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of CH2Cl2/CH3OH (100:1) as eluent to afford the corresponding scutellarein-O-alkylamine derivatives 15-18.

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 6851-80-5.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Yuan, Wen; Liu, Qiang; Shi, Yikun; Ang, Wei; Luo, Youfu; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 348 – 366;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, Computed Properties of C7H6F3NO

[00310] A reaction vial was charged with 2-benzyl-5-chloro-l,2,3,4-tetrahydro-2,6-naphthyridine(25.00 mg, 0.09662 mmol), 3-(trifluoromethoxy)aniline (42.8 mg, 0.000242 mol), tris(dibenzylideneacetone)dipalladium(0) (2.2 mg, 0.0000024 mol), xantphos (3 mg, 0.000005 mol), sodium tert-butoxide (14 mg, 0.00014 mol), and toluene (0.500 mL, 0.00469 mol) and tert-butyl alcohol (0.1 mL, 0.001 mol) and the vial was flushed with argon. The reaction mixture was then stirred at 110 0C in a microwave for 30 minutes. The reaction mixture was then filtered and solvent removed and the residue purified by prep HPLC to get the pure compound as a yellow solid. MS (M+H)= 400.4;1H-NMR (CDCl3): (400 MHz) 88.03 (d, 7=4.66 Hz, IH), 7.61 (bs, lH),7.48-7.44 (m, 2H), 7.40-7.28 (m, 5H), 6.83 (d, J=7.98 Hz, IH), 6.51 (d, 7=5.1 1 Hz, IH), 6.25 (bs, IH), 3.85 (s, 2H), 3.70 (s, 2H), 3.00 (t, J=5.50 Hz, 2H), 2.76 (t, 7=5.50 Hz, 2H)

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-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RENOVIS, INC.; WO2009/11904; (2009); 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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., name: 4-(2-Methoxyethoxy)aniline

To a solution of 2.4-dichloro-l,3,5-triazine A.91 (2 g, 13.34 mmol) in DMF (10 mL) at 0 0C were added DIEA (2.4 mL, 13.77 mmol) and 4-(2-methoxyethoxy)benzenamine (2.027 g, 12.12 mmol) and the mixture was stirred at 0 0C for 30 minutes and then room temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (50 mL x 1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The brown solid was purified by silica gel column chromatography using 30% of ethyl acetate in hexane as eluent to give 4-chloro-N-(4-(2-methoxyethoxy)phenyl)-l,3,5-triazin-2-amine A.92 (2.887 g, 84.8% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 10.58 (1 H, s), 8.56 (1 H, d, J=5.9 Hz), 7.51 (2 H, t, J=9.5 Hz), 6.96 (2 H, t, J=7.9 Hz), 4.04 – 4.1 1 (2 H, m), 3.65 (2 H, dd, J=5.3, 3.8 Hz), 3.31 (3 H, s); Mass Spectrum (ESI) m/e = 281.0 [M+l].

The synthetic route of 33311-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
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Application of 363-47-3, These common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, 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.

To glacial acetic acid (4.0 mL) precooled to 5 C were added potassium thiocyanate (4.0 mmol) and 2,6-difluoro-p-anisidine (1) (1.0 mmol). The mixture was stirred vigorously while 1.1 mmol of bromine in 1.5 mL of glacial acetic acid was added drop-wise such that the temperature did not rise beyond 0 C. After all the bromine was added (60 min), the solution was stirred for another 2 h at 0 C and at ambient temperature for 10 h. It was allowed to stand overnight, during which a yellowish-orange precipitate settled out. Water (30 mL) was added and the solution was adjusted to pH 6 with sat aq NaHCO3. The mixture was extracted with dichloromethane (3 × 50 mL) and the combined extracts were dried over Na2SO4 and evaporated to give a yellowish-orange solid as the crude product. Flash chromatography using hexane:dichloromethane 2:3 gave a dark yellow solid in 56% yield.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pirrung, Michael C.; Biswas, Goutam; De Howitt, Natalie; Liao, Jiayu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 20; (2014); p. 4881 – 4883;,
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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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 349-55-3

EXAMPLE 68 Synthesis of 2-[(3-methoxy-5-(trifluoromethyl) phenyl)amino]phenylacetic Acid In the manner described in example 3, 2-bromophenylacetic acid is condensed with 3-methoxy-5-(trifluoromethyl)aniline to yield 2-[(3-methoxy-5-(trifluoromethyl)phenyl)amino]phenylacetic acid.

According to the analysis of related databases, 349-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Exocell, Inc.; US6355680; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 1758-46-9, name is 2-Phenoxyethylamine, 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 1758-46-9, Computed Properties of C8H11NO

General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3).

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:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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Application of 41365-75-7, 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. 41365-75-7 name is 1-Amino-3,3-diethoxypropane, 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.

Intermediate 6; EPO To a solution of Intermediate 4 (1.40 g, 3.49 mmol), 1 -amino-2,3-diethoxypropane (513 mg, 3.49 mmol), and DIPEA (2.25 g, 17.45 mmol) in DMF (50 ml) was added HATU (1.592 g, 4.19 mmol). The solution was allowed to stand at RT for 2 h and the DMF was evaporated. The residue was partitioned between EtOAc (150 ml) and sat. aqueous NaHCO3 (200 ml). The organic layer was separated and the aqueous was extracted further with EtOAc (2 x 150 ml). The combined extracts were washed with water (200 ml), brine (100 ml), dried (Na2SO4) and evaporated. The crude product was purified on an lsolute SPE Si Il cartridge (20 g) eluting with 40-60% EtOAc in pentane and then 100% EtOAc to afford a cream solid.Yield: 1.59 g (86%)LC-MS (Method 3): Rt 3.06 min, m/z 553 [MNa]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-3,3-diethoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; ARGENTA DISCOVERY LTD.; WO2006/136857; (2006); A1;,
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Synthetic Route of 6738-23-4,Some common heterocyclic compound, 6738-23-4, name is 2,4-Dimethylanisole, molecular formula is C9H12O, 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.

Step A Preparation of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide To a solution of 2.72 g. (0.02 mole) of 2,4-dimethylanisole in 20 ml. of acetic acid and 2 ml. of sulfuric acid was added (2.47 g., 0.02 mole) 2-chloro-N-(hydroxymethyl)acetamide at < 20 C. over a 10 minute period with stirring. After standing at room temperature about 20 hours the mixture was poured with stirring into 250 ml. of ice-water. After 1 hour the precipitate was collected, washed with water and dried at 60 C. and recrystallized 3 times from methanol:water (3:2), once from ethanol:water (3:2) and twice from ethanol:water (1:1) to give 0.34 g. of 2-chloro-N-[2-methoxy-3,5-dimethylphenyl]methyl acetamide, m.p. 124-124.5 C. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dimethylanisole, its application will become more common. Reference:
Patent; Merck & Co., Inc.; US4092414; (1978); A;,
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