Tag: M.W=100-200

1579-40-4, The chemical industry reduces the impact on the environment during synthesis 1579-40-4, name is Di-p-tolyl Ether, I believe this compound will play a more active role in future production and life.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The chemical industry reduces the impact on the environment during synthesis Di-p-tolyl Ether. I believe this compound will play a more active role in future production and life.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-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 cyanuric chloride(0. 368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39mL, 2.2 mmol) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg,30percent), mp91-92 C ; HPLC : Inertsil ODS-3V C18, 40: 30: 30[KH2PO4(0. 01 M, pH3. 2):CH30H : CH3CN], 264nm, Rt 8.6 min, 99.1percent purity; MS(ESI) : m/z 331 (M+H, 100), 305 (0.8), 151 (. 3).

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 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); 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 126-38-5 as follows. 126-38-5

To a solution of 4-bromopyridin-2-amine (1.08 g, 6.24 mmol) in H20 (20 mL) were added l-bromo-2,2-dimethoxypropane (5.59 g, 30.5 mmol) and 4-methylbenzenesulfonic acid (209.4 mg, 1.216 mmol). The reaction mixture was heated to reflux and stirred for 12 hours and then adjusted to pH = 10 with saturated Na2C03 aqueous solution, the resulting mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc(v/v) = 3/1) to give the title compound as a yellow solid (750 mg, yield 57%).MS (ESI, pos. ion) m/z: 211.1 [M+H]+.

According to the analysis of related databases, 126-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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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: Two mmol 5b1?5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 ¡ãC. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 ¡ãC. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1?6b20.

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

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
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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. 1484-26-0, name is 3-Benzyloxyaniline, A new synthetic method of this compound is introduced below., 1484-26-0

Example 37; Preparation of Intermediate Compound 37C; Step A ~ Synthesis of Compound 37B; Compound 37A (commercially available) (10.0 g, 50.25 mmol) was dissolved in water at room temperature and to resulting suspension K2CO3 ( 3.8 g, 27.64 mmol) was added. 3- Chloro propionylchloride (7.0 g, 55.28 mmol) was added dropwise for 30 minutes and stirred for 2 hours at RT. The precipitate was filtered and washed with water, 1 N HCl, dried at 50 0C under vacuum overnight to give 7.2 g of the product 37B.

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; SCHERING CORPORATION; WO2009/32123; (2009); A2;,
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A common compound: 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. 54149-17-6

(Synthesis of Charge Transporting Compound L); [Show Image] Under nitrogen atmosphere, Compound G (0.17 g, 0.31 mmol) and 9.5 g of N,N-dimethylformamide were placed in a 50-ml three-necked flask, and 0.03 g (0.63 mmol) of sodium hydride (60% oil dispersion) was added thereto. Then, the mixture was stirred for 30 minutes. The temperature was raised to 50C. Then, 0.07 g (0.41 mmol) of the above-described halogen compound K was added dropwise thereto, and the mixture was stirred for 7 hours. The reaction liquid was poured into 20 ml of water, and extraction was performed twice with 20 ml of ethyl acetate. The obtained organic layer was washed twice with 20 ml of water. After the organic layer was concentrated by using an evaporator, the obtained residue was purified by silica gel chromatography (10 g of silica gel was used; elution was performed by using 200 ml of hexane/ethyl acetate =2:1 (volume ratio) ; and further elution was performed by using 200 ml of ethyl acetate). Thus, 0.14 g (Yield: 69.3%) of Compound L was obtained. 1H-NMR (270 MHz, CDCl3): delta 2.01 (m, 2H), 2.89 (t, 2H), 3,37 (s, 3H), 3.48-3.58 (m, 4H), 3.58-3.70 (m, 6H), 7.20-7.35 (m, 4H), 7.35-7.53 (m, 7H), 7.63 (d, 4H), 7.81 (d, 4H), 7.98 (s, 1H), 8.14 (m, 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, 54149-17-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2116531; (2009); A1;,
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111-95-5, Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, 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 111-95-5.

To the product from step 2 (1.00 g, 5.29 mmol) in ACN (20 mL) was added bis(2- methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 0C for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCI3) .delta 7.47 (bs, 2 H), 3.77 (t, J = 5.7 Hz, 4 H)1 3.52 (t, J = 5.4 Hz, 4 H), 3.25 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 154.7 (s), 152.0 (s), 120.9 (s), 1 19.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t). LCMS (50-95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 4.91 min on 250 mm column, (M+H)+ = 286, (M+Na)+ = 308, (M+Na+ACN)+ = 349.

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
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Adding some certain compound to certain chemical reactions, such as: 437-82-1, name is 2,6-Difluoroanisole, 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 437-82-1. 437-82-1

To a solution of l,3-difluoro-2-methoxy-benzene (3.0 g, 20.8 mmol) in tetrahydrofuran (30 mL) at -70 C was added dropwise n-butyl lithium (1.6 g, 25.0 mmol). The reaction was stirred for 30 mins. Then N,N-dimethylformamide (4.6 g, 63 mmol) was added, and stirring was continued for another 30 minute. The cold bath was removed, and the reaction mixture was stirred at 15 C for 1 hour. On completion, the mixture was extracted with ethyl acetate (2 x 15 mL). The aqueous phase was acidified with 4 M hydrochloric acid and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over sodium sulfate and evaporated in vacuo to give compound B-256 (3.0 g, 84% yield) as a light yellow liquid. LCMS (B): tR=0.624 min., 173.1 m/z (M+l).

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 2,6-Difluoroanisole.

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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2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, A new synthetic method of this compound is introduced below.

Example 189Preparation of rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide; A mixture of rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (86.2 mg, 0.20 mmol), 2,2′-oxybis(ethylamine) (31.3 mg, 0.3 mmol), 2-(7-azabenzotriazol-1-yl)-n,n,n’,n’-tetramethyluronium hexafluorophosphate (HATU, 76 mg, 0.2 mmol) and iPr2NEt (0.1 mL, 0.55 mmol) in CH2Cl2 (2 mL) was stirred at rt overnight. The mixture was then diluted with CH2Cl2 and washed with water, brine. The organic phase was separated, filtered and dried over Na2SO4. The mixture was then concentrated and purified by reverse phase chromatography (20-95% of ACN/water) to give rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide (20.3 mg, 19.6%) as an off-white powder. HRMS (ES+) m/z Calcd for C27H34Cl2N4O2+H [(M+H)+]: 517.2132, found: 517.2133

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; Ding, Qingjie; Jiang, Nan; Liu, Jin-Jun; Ross, Tina Morgan; Zhang, Jing; Zhang, Zhuming; US2010/75948; (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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22236-10-8

General procedure: Commercially available substituted aniline (63.4mmol) was portionwise added to a solution of concentrated HCl (13mL), ethanol (20mL) and water (7mL). To the above mixture was added dropwise a solution of NaNO2 (4.69g, 69.7mmol) in water (15mL) at 0-5C. After the completion of addition, the reaction mixture was stirred at this temperature for 30min, and then added into a mixture of ethyl 2-chloroacetoacetate (10.88g, 63.4mmol), anhydrous sodium acetate (15.60g, 190.10mmol), and water (90mL) at 0C. The reaction mixture was stirred at 0C for 10min and then at room temperature for 4h. The solid which precipitated was collected by filtration and recrystallized from ethanol to afford light yellow solids (21a-21m) in 75.2-90% yields. 6.3.3 Ethyl 2-chloro-2-(2-(4-(difluoromethoxy)phenyl)hydrazono)acetate (21c) Yellow solid; Yield: 78.9%; M.p.: 120.8-121.6 C; MS (ESI) m/z(%): 315.1 [M+Na]+.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Ju; Nie, Minhua; Wang, Yanjing; Hu, Jinxing; Zhang, Feng; Gao, Yanlin; Liu, Yajing; Gong, Ping; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 431 – 446;,
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