Category: ethers-buliding-blocks

Application of 29026-74-2, 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. 29026-74-2 name is 2-Isopropoxyaniline, 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: Ethyldiisopropylamine (EDIPA) (0.326 mL, 1 .87 mmol, 1 .0 eq) was added to a solution of 2-(2-chloroethanamido)benzoic acid (0.400 g, 1 .87 mmol) at 25C in dioxane (10 mL) and stirred for 2 minutes before the dropwise addition of phosphorous trichloride (0.309 mL, 2.25 mmol, 1 .2 eq). After 5 minutes of stirring, O-isopropoxyaniline (0.31 1 g, 2.06 mmol, 1 .1 eq) was added, and the resulting mixture was heated to 70C and stirred for an additional 6 hours. Upon completion, the reaction was carefully quenched with saturated aqueous NaHC03, diluted with water, and extracted 3 times with EtOAc. The combined organic layers were dried (Na2SO4), concentrated, and the crude material was purified by combi flash 0 to 50% EtOAc in hexanes to provide 2-(chloromethyl)-3-(2-isopropoxyphenyl)quinazolin-4(3H)-one (333 mg, 54% yield).1H NMR (400 MHz, CDCI3): delta 8.32 p.p.m. (m, 1H), 7.89 (m, 1H), 7.54 (m, 1H), 7.38 (dd, J1=7.7, J2=1.6, 1H), 7.11 (m, 1H), 4.58 (hept, J= 1.5 Hz, 1H), 4.38 (d, J=12 Hz, 1H), 4.19 (d, J=12 Hz, 1H), 1.26 (d, J=6.1, 3H), 1.17 (d, J=6.1, 1H), 13C NMR (125 MHz): delta 161.6, 153.0, 152.4, 147.2, 134.5, 131.1, 130.8, 127.6, 127.5, 127.3, 125.3, 121.4, 121.0, 114.3, 71.2, 43.7, 22.2, 21.8; HRMS (m/z): [M+] calculated for C18H17CIN2O2 328.79, found 329.1

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

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; STOCKWELL, Brent R.; WELSCH, Matthew; YANG, Wan Seok; WO2014/11973; (2014); A2;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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. Recommanded Product: 645-36-3

The 2,2-Diethoxy-ethylamine (1852.5 g; 1.00 equiv; 13.63 moles), 3,5-dichloro-benzaldehyde (2453 g; 1.00 equiv; 13.60 moles), and Toluene (12 L) is charged to a 22 L flask equipped with a Dean Stark trap, condenser, nitrogen inlet, overhead stirring, and thermocouple. The light yellow reaction is warmed to reflux. Solvent begins distilling at 88 C. A total of 650 mL distillate (240 mL of water) is collected. The temperature is increased to 114 C. during the distillation. NMR after 2 hr at reflux shows the product. The heat is shut off after 2.5 hr. The solution is gravity filtered into a carboy through fluted filter paper to remove a few particulates (including a small section of glass tubing, which is most likely from the 3,5-dichloro-benzaldehyde). The filtered solution is concentrated using Buchi flask with the water bath set at 45 C. Once the solvent stops coming over, the temperature is increased to 70 C. with full vacuum and held for 1.5 hr to remove any residual toluene. The weight of (3,5-Dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine is 4059.3 g (102.9% of theory). Mass Spectrum (LCMS) m/z=291.2) (M+H+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common.

Reference:
Patent; Joseph, Sajan; Li, Renhua; Myers, Michael Ray; Aburub, Aktham; Dai, Jenny Pingqi; Schmid, Christopher Randall; US2009/221633; (2009); A1;,
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Related Products of 162705-07-9, 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. 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the appropriate piperidine (pyrroline) nitroxyl acids (0.5 mmol), compound 3 (0.5 mmol) and DMAP (20 mg) was stirred in anhydrous CH2Cl2 (20 mL) for 5 min at room temperature under nitrogen. DCC (106 mg, 0.5 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was filtered and the filtrate was evaporated. The residue was subjected to column chromatography on silica gel with CH2Cl2-acetone to afford target compounds 14a-d, and their structures were confirmed from mp, IR, ESR and HRMS analyses.

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, (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Ying-Qian; Li, Xiao-Jing; Zhao, Chun-Yan; Nan, Xiang; Tian, Jing; Morris-Natschke, Susan L.; Zhang, Zhi-Jun; Yang, Xiao-Ming; Yang, Liu; Li, Lin-Hai; Zhou, Xing-Wen; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1248 – 1256;,
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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101-55-3

4-Bromodiphenyl ether (X = Br) (3.74 g, 15 mmol) was dissolved in 1,4-dioxane (50 ml)Addition of pinacol diboronate(4.52 g, 18 mmol),Potassium acetate (1.78 g, 18 mmol).Then, the catalyst [1,1′-bis (diphenylPhosphine) ferrocene] palladium dichloride [Pd (dppf) 2Cl2] (1.5 mmol, 1.11 g).With stirring, heated to 100 C, the reaction 5h (TLCDetection of raw materials disappear).Then, Intermediate (14) (4.44 g, 10 mmol) was added, and the reaction was maintained at 100 C for 22 hours14 disappears).Then, after distilling off the organic solvent, Intermediate (9) (yellow solid, 3.41 g, yield 70%, chemical purity and optical purity> = 99%) was obtained.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Liu Guobin; (12 pag.)CN104557945; (2017); B;,
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Electric Literature of 707-07-3, 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 707-07-3 as follows.

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL¡Á3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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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. 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H7F3N2O

Step a. To a solution of 4-(trifluoromethoxy)benzene-l,2-diamine (CAS Number 658-89-9; 0.45 g, 2.34 mmol) in DMF (5 ml) was added urea (0.28 g, 4.66 mmol) at rt. The resulting reaction mixture was heated at 150C for 20 h. The reaction mixture was diluted with water (5 ml) and the brown precipitate was collected by vacuum filtration and dried under reduced pressure to yield 5- (trifluoromethoxy)-l,3-dihydro-2H-benzo[d]imidazol-2-one (0.28 g, 1.28 mmol). LCMS: Method C, 2.118 min, MS: ES+ 219.

The synthetic route of 658-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; STOCKLEY, Martin Lee; KEMP, Mark Ian; MADIN, Andrew; (88 pag.)WO2018/60742; (2018); A1;,
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Synthetic Route of 171290-52-1, The chemical industry reduces the impact on the environment during synthesis 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, I believe this compound will play a more active role in future production and life.

(S) -3- (5-amino-3-bromo-4-cyano-1H -Pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7c (5g, 14.1mmol), cuprous iodide (0.6g, 2.8mmol), triethylamine (9mL), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride (2g, 2.8mmol) And N, N-dimethylformamide (150mL) were heated to 80 C under the protection of argon, and 1-ethynyl-3,5-dimethoxybenzene (14g, 84.5mmol) was added in portions. And stir for 2 hours.After cooling to room temperature, the reaction solution was poured into water and extracted with ethyl acetate (200 mL ¡Á 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the drying agent, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5/1) to obtain the target product (S) -3- ( 5-amino-4-cyano-3-((3,5-dimethoxyphenyl) ethynyl) -1H-pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7d (5 g, brown oil), yield: 81%.

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, 3,5-Dimethoxyphenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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Application of 261762-35-0, 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. 261762-35-0 name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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.

Example 20 N-( 1 -(7-chloro-4,5 -difluoro- 1 -hydroxy- 1 ,3-dihydrobenzo[cl [ 1 ,2″|oxaborol-6-yloxy”)-2-cva nopropan-2-yl)-4-(trifluoromethoxy)benzamide To a solution of 5-bromo-l,2-difluoro-3-methoxybenzene (8.9 g, 39.9 mmol) in THF (200 mL), LDA (17.6 mL, 43.9 mmol) is added dropwise at -78C and the mixture is stirred at the same temperature for 2 h. DMF (9.6 g, 131.7 mmol) is added at -78 C, and the mixture is stirred at -78C for 4 h. The reaction is quenched with saturated aq. NH4C1, extracted with EA, dried over Na2S04, and recrystallized to afford the desired product as a white solid (6 g, yield 60 %). :H NMR (400 MHz, CDC13): delta 10.20 (s, IH), 7.04-7.06 (m, 1H), 3.99 (s, 3H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1,2-difluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; ANACOR PHARMACEUTICALS INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; PLATTNER, Jacob J.; PULLEY, Shon Roland; WHITE, William Hunter; ZHANG, Yong-Kang; ZHOU, Yasheen; WO2014/149793; (2014); 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-(2-Bromoethoxy)-4-fluorobenzene

EXAMPLE 113 4-(3-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR149 From a mixture of 4-(3-fluorobenzyl)piperidine hydrochloride (500 mg, 2.18 mmol), 2-(4-fluorophenoxy)ethyl bromide (501 mg, 2.29 mmol) and K2 CO3 (615 mg, 4.45 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (360 mg, 81%): mp 155-157 C., 1 H NMR (CDCl3) 1.65-1.90 (m, 3H), 1.98-2.16 (m, 2H), 2.62 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.53 (m, 2H), 3.67 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-7.10 (m, 7H), 7.19-2.28 (m, 1H), 12.64 (bs, 1H); Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.35; H, 6.58; N, 3.77.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; Cocensys, Incorporated; US6124323; (2000); A;,
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Electric Literature of 16452-01-0, The chemical industry reduces the impact on the environment during synthesis 16452-01-0, name is 3-Methoxy-4-methylaniline, I believe this compound will play a more active role in future production and life.

g. 2-bromo-5-methoxy-4-methyl-aniline. To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 H).

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-4-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfahl, Magnus; Tachdjian, Catherine; Spruce, Lyle W.; Al-Shamma, Hussien A.; Boudjelal, Mohamed; Fanjul, Andrea N.; Wiemann, Torsten R.; Pleynet, David P.M.; US2003/144329; (2003); A1;,
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