Author: Jessica.F

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 50592-87-5 as follows. Computed Properties of C7H15BrO

(3) Production of 4′-methoxyhexyloxy-biphenyl-4-carboxylic acid. 8.4 Grams of 1-bromo-6-methoxyhexane and 4.5 g of 4′-hydroxybiphenyl-4-carboxylic acid were refluxed in 100 ml of water and 400 ml of ethanol for 4 hours. Concentrated hydrochloric acid was added to the reaction mixture so that the mixture showed pH 1, then 150 ml of water was added, and the resultant mixture was refluxed for 1 hour. The reaction mixture was cooled to precipitate a crystal, and the crystal was recovered by filtration. The so-obtained crystal was recrystallized from acetone. Yield 55%.

According to the analysis of related databases, 50592-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; US5340498; (1994); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

General procedure: A microwave vial (2?5mL) was charged with 1 equiv of mon-subtituted triazine in acetonitrile. Then 1.1 equiv of DIPEA and 1 equiv of aryl amine derivative were added. The vial was sealed and heated under microwave irradiated between 10 and 180 min at 150°C. After completion of the reaction (monotored by TLC), the solvent was removed by vacuum evaporation. The resultant mixture was dissolved in EtOAc or CH2Cl2, a solution of 2N HCl was added then water. The layer organic was extracted whit EtOAc or CH2Cl2 and dried with MgSO4, The product was purified by silica gel chromatography or recrisallized in ethanol 95.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tber, Zahira; Wartenberg, Mylene; Jacques, Jean-Eddy; Roy, Vincent; Lecaille, Fabien; Warszycki, Dawid; Bojarski, Andrzej J.; Lalmanach, Gilles; Agrofoglio, Luigi A.; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4310 – 4319;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 64465-53-8, 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 64465-53-8 as follows.

1 ,1 -Dimethylethyl 4-{[4-fluoro-3-(methyloxy)phenyl]amino}-1 – piperidinecarboxylate (D9)A solution of 1 ,1-dimethylethyl 4-oxo-1 -piperidinecarboxylate (1.41g, 7.1mmol) and 4-fluoro-3-methoxyaniline (1g, 7.1mmol) was stirred at room temperature for 1h. Sodium tri(acetoxy)borohydride (1.95g, 9.2mmol) was then added and stirring continued over-weekend. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution, dried and then concentrated in vacuo. Column chromatography eluting with 0-50% Et2C7petroleum ether gave the title compound as a white solid (1.45g). deltaH (CDCI3, 400MHz) 6.89 (1 H1 dd), 6.22 (1 H, dd), 6.09 (1H1 m), 4.03 (2H, br s), 3.84 (3H, s), 3.36 (1 H, br s), 2.92 (2H, m), 2.03 (2H, m), 1.46 (9H, s), 1.32 (2H, m).

According to the analysis of related databases, 64465-53-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/144400; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 867288-00-4, name is 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Difluoro-3′-methoxy-[1,1′-biphenyl]-4-amine

A solution of 123 L of a 10% aqueous solution of Na2C03, 1.5 L of a 25 wt. % aqueous solution of ammonia and 2.0 kg of a filtration resin (Dicalite) were charged to the reactor and the mixture stirred for 5 minutes. The mixture was recirculated through a filter until clarification of the liquors (35 min) and charged into a reactor. 60 L of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1 +01 ) were allowed to separate. The aqueous phase (A1 ) was transferred to a different reactor and 60 L of isopropyl acetate were charged. The mixture was stirred and the phases (A2 + 02) were allowed to separate. Both organic phases (01+02) were charged into a reactor and 108 L of a 10 wt. % aqueous solution of Na2C03 were added. The mixture was stirred and the phases (A3+03) were allowed to separate. The organic phase (03) was stirred with 108 L of a 10 wt. % aqueous solution of Na2C03 and the phases (A4+04) were allowed to separate. The organic phase (04) was stirred with 100 L demineralised water and the phases (A5+05) were allowed to separate. The organic phase (05) was filtered over a filtration resin (Dicalite) in a filter and charged in to a reactor. 2.2. Distillation: The organic phase (05) was distilled during 2 hours under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65 C.

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; ALMIRALL, S.A.; BOIX BERNARDINI, Maria, Carmen; WO2011/45059; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

A solution of [2-(trifluoromethyl)phenyl]acetic acid (3.06 g, 15.0 mmol) in toluene (30 mL) was heated to 80C, 1,1-di-tert-butoxy-N,N-dimethylmethaneamine (14.4 g, 60.0 mmol) was added and the mixture was stirred at 80C for 2 hr. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The obtained extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.16 g, 81%). To a solution of tert-butyl [2-(trifluoromethyl)phenyl]acetate (3.10 g, 11.9 mmol) in DMF (36 mL) was added sodium hydride (60% oil, 524 mg, 13.1 mmol), and the mixture was stirred at room temperature for 30 min. 1-Chloro-3-iodopropane (1.34 mL, 12.5 mmol) was added, and the mixture was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100 – 30/70) to give tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.63 g, 91%). A solution of tert-butyl 5-chloro-2-[2-(trifluoromethyl)phenyl]pentanoate (3.56 g, 9.83 mmol) in TFA (10 mL) was stirred at room temperature for 18 hr. The solvent was evaporated under reduced pressure, ethyl acetate was added, and the mixture was extracted with 1 M aqueous sodium hydroxide solution. The extract was acidified with 6 M hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (2.74 g, 99%). 1H NMR (CDCl3) delta: 1.55 – 1.75 (1 H, m), 1.76 – 2.04 (2 H, m), 2.16 – 2.34 (1 H, m), 3.50 (2 H, t, J=6.3 Hz), 4.06 (1 H, t, J=7.3 Hz), 7.31 – 7.45 (1 H, m), 7.46 – 7.62 (2 H, m), 7.67 (1 H, d, J=7.7 Hz).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2455380; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 36865-41-5, name is 1-Bromo-3-methoxypropane, 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 36865-41-5, Recommanded Product: 1-Bromo-3-methoxypropane

Step 2: N’-Isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester To a solution of hydrazinecarboxylic acid tert-butyl ester (4.67 g, 27.16 mmol) in toluene (90 mL) was added pulverized potassium hydroxide (1.98 g, 35.3 mmol) and tetrabutylammonium hydrogensulfate (904 mg, 2.72 mmol). The solution was heated to 50 C. in a preheated oil bath and 1-bromo-3-methoxypropane (3.67 mL, 32.6 mmol) was added drop-wise over 45 minutes. The solution was then heated to 80 C. for 3 h. The solution was cooled to room temperature and washed with water (3*150 mL) until the water layer was neutral. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide N’-isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester as a viscous oil (6.49 g, 98%), which was used without further purification. Mass spectrum: m/z: 245.4 (M+1).

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, 1-Bromo-3-methoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 80936-82-9, name is 4-(Methoxymethyl)aniline, A new synthetic method of this compound is introduced below., Quality Control of 4-(Methoxymethyl)aniline

Example 82 Synthesis of 4-amino-1-(4,4-difluorocyclohexyl)-N-(4-(methoxymethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide 33 mg of methyl-4-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate obtained in step 2 of Reference Example 10 was dissolved in 2 mL of methanol. 0.05 mL of a 5M aqueous sodium hydroxide solution was added thereto at room temperature, and the mixture was stirred at 60 C. for 1 hour. After cooling, 0.2 mL of a 5M aqueous hydrochloric acid solution was added, and the mixture was concentrated under reduced pressure. The obtained solid was suspended in 2 mL of DMF, and 17 mg of 4-(methoxymethyl)aniline, 60 mg of HATU, and 0.055 mL of N,N-diisopropylethylamine were added thereto at room temperature, followed by stirring at the same temperature for 1 hour. The reaction solution was diluted with ethyl acetate, and washed with water and a saturated aqueous sodium chloride solution. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The obtained residue was suspended in methanol, and filtered, followed by drying at 60 C. under reduced pressure, thereby obtaining 29 mg of the title compound.

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; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 645-36-3, A common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

General procedure: To a suspension of the appropriate quinolonecarboxylic acid (1mmol) in 6mL of dry THF at 25C, HOBt (1.5mmol), WSC (1.5mmol) and the appropriate aminoalcohol (1.5mmol) were added sequentially. The mixture was stirred at room temperature under nitrogen, then the solvent was evaporated, water was added and the solid formed filtered. The crude product was purified by flash chromatography.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Beretta, Giangiacomo; Dallavalle, Sabrina; Tetrahedron; vol. 70; 52; (2014); p. 9797 – 9804;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 17061-62-0,Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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.

N,N-bis(4-methoxybenzyl)ethanesulfonamide, Example 12.0. To a solution of bis(4-methoxybenzyl)amine 12.01 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq), followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer extracted with DCM (2 x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10- 80% EtOAc in hexanes) to provide the title compound 12.0 (1125 g, 3.22 mol, 92%) as white solid. ?H-NMR (400 MHz, CDC13) 7.23 (dd, J= 2.08, 6.62 Hz, 4H), 6.90 (dd, J= 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (s, 6H), 2.92 (q, J 7.40 Hz, 2H), 1.33 (t, J 7.40 Hz, 3H). GC-MS (ESI pos. ion) m/z: 372.2 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(4-methoxybenzyl)amine, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

[0403] To a solution of 5-acetyl-N-(2,6-diethylphenyl)-1-methyl-1H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), N,N-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80 C. for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017 g, 78% yield). [0404] 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1H), 7.71 (d, J=12.33 Hz, 1H), 7.36 (s, 1H), 7.21 (t, J=7.60 Hz, 1H), 7.12 (d, J=7.60 Hz, 2H), 5.75 (d, J=12.33 Hz, 1H), 4.18 (s, 3H), 3.16 (s, 3H), 2.92 (s, 3H), 2.52 (q, J=7.57 Hz, 4H), 1.09 (t, J=7.57 Hz, 6H) [0405] HRMS (ESI) calcd for C20H27N4O2 [M+H]+ 355.2129. found 355.2133.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; Casuscelli, Francesco; Brasca, Maria Gabriella; Caldarelli, Marina; Cervi, Giovanni; Disingrini, Teresa; Quartieri, Francesca; US2014/51708; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem