Author: Jessica.F

Electric Literature of 29026-74-2, The chemical industry reduces the impact on the environment during synthesis 29026-74-2, name is 2-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

EXAMPLE 4 Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (15 g) and 2-(1-methylethoxy)aniline (11.5 g) are added to ethanol (100 ml), and the mixture is refluxed with stirring for 17 hours. After cooling, the precipitate is collected by filtration and recrystallized from DMF to give ethyl 1,6-dihydro-2-[2-(1-methylethoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (8.5 g). M.p. 205-207 C. Elemental analysis for C16 H19 N3 O4: Calcd. (%): C, 60.56; H, 6.03; N, 13.24. Found (%): C, 60.73; H, 6.12; N, 13.40. IR numaxnujol cm-1: 3000-3300 (NH), 1720 (C=O), 1600 (C=O). NMR (DMSO-d6) delta: 1.34 (6H, d, J=7 Hz, OCH(CH3)2), 1.30 (3H, t, J=7 Hz, OCH2 CH3), 4.26 (2H, q, J=7 Hz, OCH2 CH3), 4.73 (1H, m, OCH(CH3)2), 6.86-7.30 (3H, m, Ar–H), 8.32 (1H, d, J-8 Hz, Ar–H), 8.53 (1H, s, C4 –H), 8.20-12.30 (2H, b, 2*NH). Mass m/e: 317 (M+).

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

Reference:
Patent; Morishita Pharmaceutical Co. Ltd.; US4666915; (1987); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene, molecular formula is C8H8Br2O2, 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: 24988-36-1

Bisdimethylaminoethyl ether (2.84 g) was dissolved in 42 mL THF and cooled in an ice bath. Isopropylmagnesium chloride (8.9 mL of a 2 M solution in THF) followed by Compound 14 (5 g dissolved in 5 mL THF) were added slowly sequentially. The mixture was allowed to warm to ambient temperature and stirred overnight. Next, 2.1 mL of 3-chloro-2-fluorobenzaldehyde was added. After stirring for ~ Ih, the mixture was quenched to pH ~ 7 with 2N HCl. The product was extracted into ethyl acetate and the organic phase was dried over sodium sulfate. The solvent was exchange to heptane to precipitate the product and a mixture of heptanes:MTBE (4:1) was added to form a slurry. After filtration the solid was slurried in toluene, filtered and vacuum dried to yield compound 15: 1U NMR (CD3CN, 400 MHz) delta 7.47 (s, IH), 7.41-7.35 (m, 2H), 7.15 (t, J = 7.4 Hz, IH), 6.66 (s, IH), 6.21 (br s, IH), 3.90 (s, 3H), 3.87 (br s, IH), 3.81 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24988-36-1, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2009/36161; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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. Formula: C9H13NO3

6-Amino-hexanoic acid (13.1 g, 100 mmoL) was dissolved in 10% aqueous Na2CO3 solution (300 mL), then dioxane (200 mL) was added to the above solution. Fmoc-CI (26 g, 110 mmoL) was added to the above mixture portion-wise, and the resultant reaction mixture was stirring for 12h. The mixture was extracted with ether (150 mL X 2), and the aqueous portion was acidified by 6N HCI. The mixture was filtered, and the solid was washed with water and dried to give 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid as a white solid (31 g, 81 %). 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid (9.17 g, 25 mmoL) and 0- (2, 4- dimethoxy-benzyl)-hydroxylamine (36 g, 26 mmoL) were dissolved in DCM (250 mL), then DCC (6.18 g, 30 mmoL) was added ortion-wise. The resultant mixture was stirred for 3h at room temperature, then cooled to 0C, filtered, and washed with DCM. The organic solution was evaporated to dryness to give the crude [5- (2, 4-dimethoxy- benzyloxycarbamoyl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester. The crude ester was reacted with piperidine (5 mL) in MeOH (150 mL) at room temperature for12 h. The solution was evaporated and the residue was purified by flash chromatography (silica, EtOAc: MeOH = 5: 1). 6-Amino-hexanoic acid (2,4-dimethoxy- benzyloxy)-amide was obtained as a white solid (4.15 g, 56%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 216067-66-2, its application will become more common.

Reference:
Patent; S*BIO PTE LTD; WO2005/40101; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 6876-00-2, name is 1-Bromo-3-phenoxybenzene, 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. COA of Formula: C12H9BrO

EXAMPLE 31 1-(2,4-Difluorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.28 g), tetrahydrofuran (2 ml), magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2,4-difluorophenyl)cyclopropane (Example 23) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C8; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2,4-difluorophenyl)-1-(2-fluoro-3-(3-phenoxyphenyl)prop-1-enyl)cyclopropane (80 mg, 56%).

The synthetic route of 1-Bromo-3-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, 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 1515-81-7, category: ethers-buliding-blocks

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), thiol (1.0 mmol), p-methoxybenzylmethyl ether (167 mL,167 mg, 1.10 mmol), TMSOTf (271 muL, 333 mg, 1.50 mmol), anddiisopropylethylamine (244 muL, 181 mg, 1.40 mmol). The homogenous mixture was stirredovernight and then passed through a column of silica (2 cm x 1 cm) with Et2O.The solvent was removed in vacuo and the residue was purified by columnchromatography (0-2% EtOAc/hexanes).

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; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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. 707-07-3, name is (Trimethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H14O3

At room temperature, 20g (74.9mmol) methyl 1-(chloroacetyl)-2-oxoindolin-6-ylcarboxylate was dissolved in 50 ml of acetic anhydride. The mixture is heated at 124 C. Add dropwise 27.28g (149.8mmol) trimethyl orthobenzoate. React for 6h in the open to distill off the volatile parts of the reaction mixture. After the reaction, cooling to room temperature, precipitated crystal. turns on lathe does solvent, using 500 ml DCM (dichloromethane) dissolving the residue, added to the 1.5L in petroleum ether, to separate out the solid, room temperature stirring 3h, ice-bath 1h, filtered to obtain yellow solid 27.4g, the target compound, the yield is 95%.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southeast University; Ji, Min; Chen, Hao; Cai, Jin; Liu, Haidong; Li, Rui; (13 pag.)(2016);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 24743-14-4, 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. 24743-14-4 name is 3-(3-Methoxyphenyl)-1-propene, 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 1; Typical procedure for the stoichiometric conversion of alkenes to alkylene carbonates using NBS and DBU[0054] NBS (266 mg, 1.5 mmol) was added to a vial comprising a magnetic stirrer, and partially dissolved using water (1 ml_). DBU (0.35 ml_, 2.4 mmol) was added to the mixture using a syringe, followed by the immediate addition of the alkene (1.5 mmol). The reaction mixture was not stirred until the onset of the reaction. The vial was then placed in a stainless steal autoclave (Parr reactor) which was pressurized with CO2 at an overall pressure of 250 psi. The reactor was not purged prior to pressurization. The reaction temperature was maintained at about 40 to about 6O0C (depending on the nature of the alkene) using a Parr temperature controller. After 2-6 hours of reaction time (depending on the nature of the alkene), the reactor was cooled to room temperature and depressurized. Ethyl acetate (1 ml_) was used to extract the organic material. Following purification by flash chromatography, the product was characterized by 1H and 13C NMR. [0055]

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

Reference:
Patent; MCGILL UNIVERSITY; WO2008/34265; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 13070-45-6, 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 13070-45-6 as follows.

General procedure: (S)-C10-BridgePHOS (2.0mg, 2.4mol%) and Pd(OCOCF3)2 (0.8mg, 2mol%) were placed into an oven dried flask under a nitrogen atmosphere, and degassed fresh dry acetone (2mL) was added. The mixture was stirred at room temperature for 1h. Then acetone was removed under vacuum and a solvent system of CH2Cl2/TFE (1/1, 1mL) was added to the mixture to afford the catalyst solution. The substrate 1 (0.15mmol) and additive (1equiv) were placed in a reaction tube under nitrogen and the above catalyst solution was added to the tube. The mixture was then degassed and transferred to a stainless steel autoclave in a glove box. After exchanging the gas three times, the hydrogenation was carried out at 35C under 60bar H2. After several hours, the reaction mixture was concentrated under reduced pressure. After alkalization with saturated NaHCO3, the percentage conversion of product was determined by 1H NMR analysis of the crude product. The organic residue was purified by flash chromatography with ethyl acetate/petrol ether (1:50) to give pure product 2. Enantiomeric excess was determined using a Daicel Chiralcel column with hexane/i-propyl alcohol as the eluant.

According to the analysis of related databases, 13070-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chao; Chen, Jianzhong; Fu, Guanghong; Liu, Delong; Liu, Yangang; Zhang, Wanbin; Tetrahedron; vol. 69; 33; (2013); p. 6839 – 6844;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 29026-74-2, 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. 29026-74-2, name is 2-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 242C 1-(2-isopropoxyphenyl)piperazine The product from Example 242B (3.5 g, 23.2 mmol) was added slowly to bis-2-chloroethylaime hydrochloride (4.96 g, 27.78 mmol) at room temperature and refluxed for 48 hours. The reaction was cooled to room temperature and sodium carbonate added (9 g) and refluxed for another 48 hours. The mixture was cooled to room temperature, filtered and the white solid partitioned between dichloromethane and 3N sodium hydroxide. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 3.2 g (63%) pink oil. 1H NMR (300 MHz, CDCl3) delta1.4 (d, 6H, J=6 Hz), 1.5-1.6 (m, 4H), 2.45-2.65 (m, 4H), 3.43 (m, 1H), 6.6-6.8 (m, 2H), 6.81-6.91 (m, 2H); MS (DCI/NH3) m/e 221 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 2-Isopropoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bhatia, Pramila A.; Daanen, Jerome F.; Hakeem, Ahmed A.; Kolasa, Teodozyj; Matulenko, Mark A.; Mortell, Kathleen H.; Patel, Meena V.; Stewart, Andrew O.; Wang, Xueqing; Xia, Zhiren; Zhang, Henry Q.; US2004/29887; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 60792-79-2, 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. 60792-79-2 name is 2,2′-Oxybis(ethylamine) dihydrochloride, 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.

N,N-(2,2′-oxybis(ethane-2.1-divfflbis(2,4,6-trimethylaniline) (Example 1 1) [0088] In a drybox, 2,4,6-trimethylbromobenzene (500.0 muL, 3.27 mmol), 2,2′- oxydiethylamine dihydrochloride (289.3 mg, 1.63 mmol), sodium terf-butoxide (706.5 mg, 7.35 mmol), 4.0 mL of dimethyoxyethane, and 10.0 mM Pd(OAc)2 / CyPF-r-Bu (81.8 muL, 8.18 x 10-4 mmol) were added to a 20 mL scintillation vial equipped with a magnetic stirbar and sealed with a cap containing a PTFE septum. The reaction was placed into a temperature controlled aluminum heating block and stirred at 100 0C for 6 h. After cooling to room temperature, the reaction mixture was partitioned between 100 mL H2O/Et2O (1 :1), the organic phase separated and dried over MgSO4, followed by the removal of all volatiles to afford 505 mg (91.0 %) of the title compound.[0089] 1H NuMR spectra were obtained at 400 MHz and recorded relative to residual protio solvent. 13C NuMR spectra were obtained at 101 MHz and recorded relative to the residual solvent resonance. The spectra recorded are as follows:Eta NuMR (CDC13, 400 MHz, 22 0C): delta 2.24 (s, 6H), 2.28 (s, 12H), 3.15 (t, J= 5.0 Hz, 4H), 3.49 (br s), 3.61 (t, J = 5.0 Hz, 4H), 6.84 (s, 4H). 13C NuMR (CDCI3, 101 MHz, 22 0C): delta 18.2, 20.5, 48.2, 70.4, 129.4, 129.8, 131.3, 143.1.

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

Reference:
Patent; UNIVATION TECHNOLOGIES, LLC; JOHNS, Adam, M.; WO2010/53696; (2010); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem