Month: November 2020

366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 55 Synthesis of N2-cycloheptyl-N4-(2-dimethylamino-ethyl)-N6-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4,6-triamine (150) Cyanuric chloride (1.84 g, 10 mmol) in CH3CN (20 mL) was cooled to about -10¡ã C. was added 3-fluoro-p-anisidine (1.41 g, 10 mmol) followed by DIEA (1.8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight. N,N-dimethylethylenediamine (1.1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrous K2CO3. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g, 28percent), mp 73-76¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 10.8 min, 95.1percent purity; MS (ESI): m/z 418 (M+H, 100), 373 (11.9), 322 (7.8), 277 (6.8), 162 (3.6).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jizhen; Xu, Wenbin; Ding, Junshuai; Lee, Kuo-Hsiung; Tetrahedron Letters; vol. 57; 11; (2016); p. 1205 – 1209;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

19056-40-7, The chemical industry reduces the impact on the environment during synthesis 19056-40-7, name is 4-Bromo-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

To a stirred solution of 4-bromo-3-methoxyaniline (0.5 g, 2.47 mmol) in toluene (5 mL) were added ethylacetoacetate (0.5 mL, 3.71), sodium ethoxide (0.34 g, 4.94 mmol), and heated to110¡ãC for 16 h. After completion of the reaction, the reaction mixture was diluted with EtOAC(100 mL), washed with water (100 mL), brine (100 mL), dried over sodium sulphate andconcentrated. The residue was purified by colunm chromatography by using silica gel (60-120mesh) to afford the title product as yellow solid (0.4 g, 90percent). 1H NMR (400 MHz, DMSO-d6): oe10.21 (s, 1H), 7.48?7.43 (m, 2H), 7.11?7.08 (m, 1H), 3.83 (s, 3H), 3.54 (s, 2H), 2.20 (s, 3H); ES-MS: mlz 286.1 (M-i-1).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; WO2015/104653; (2015); A1;,
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These common heterocyclic compound, 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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. 35822-58-3

General procedure: A mixture of p-anisaldehyde (2.00 g, 1.79 mL, 14.7 mmol), thiourea (3.35 g, 44.1 mmol, 3.0 equiv), and ethyl acetoacetate (5.73 g, 5.56 mL, 44.0 mmol, 3.0 equiv) in isopropanol (20 mL) was stirred at room temperature as iron(III) tosylate (0.497 g, 0.734 mmol, 5.0 mol %) was added. The reaction mixture was heated at 70 C (temperature controlled hot plate). After 15 h, the mixture was cooled to room temperature. The solvent was then removed on a rotary evaporator, and the residue was recrystallized (ethanol) to yield 5.48 g of an off-white solid. This solid was then triturated using methanol/water (1:1) to yield 3.75 g (83%) of a light off-white solid.

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 35822-58-3.

Reference:
Article; Starcevich, Jacob T.; Laughlin, Thomas J.; Mohan, Ram S.; Tetrahedron Letters; vol. 54; 8; (2013); p. 983 – 985;,
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Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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. 20469-65-2

A mixture of 1-bromo-3,5-dimethoxy-benzene (9.6 g, 44 mmol), CuI (0.7 g, 3.6 mmol), NaI (13.3 g, 88 mmol) and MeNHCH2CH2NHMe (0.78 mL) in 1,4-dioxane (80 mL) was degassed and filled with nitrogen in a sealed tube. The reaction mixture was heated at 120 C. for 20 h. The mixture was cooled to room temperature. Water (100 mL) was added, and the mixture was extracted with ethyl acetate (2*60 mL). The organic layers were washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (10 g, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Patent; HINMAN, Andrew W.; Davis, Dana; Kheifets, Viktoria; US2014/256830; (2014); A1;,
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Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 366-99-4, name is 3-Fluoro-4-methoxyaniline, 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 366-99-4, 366-99-4

Cyclobutanone (14.0 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford N-Cyclobutyl-3-fluoro-4-methoxyaniline (2.4 g, 61percent yield). 1H NMR (300 MHz, CDC13) delta ppm 6.81 (t, J= 9.1 Hz, 1H), 6.40-6.19 (m, 2H), 3.82 (s, 3H), 3.79-3.77 (m, 1H), 3.65 (s, 1H), 2.50-2.30 (m, 2H), 1.80-1.78 (m, 4H).

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

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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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. 2752-17-2 name is 2,2′-Oxydiethanamine, 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. 2752-17-2

For the synthesis of H2L, salicylic aldehyde (10 mmol, 1.22 g) in EtOH(5 mL) was added dropwise into a 5-mL EtOH solution of 3-oxapentane-1,5-diamine (5 mmol,0.52 g). Then, the solution was stirred for 4 h at 78 C. After cooling to room temperature, the precipitate was filtered. The product was dried in vacuo, and a yellow crystalline solid obtained. Yield: 1.19 g (68.5 %). Calcd. (%) forC18H20O3N2: C, 69.21; H, 6.45; N, 8.97. Found (%): C, 69.09; H, 6.54; N, 8.83.1H NMR (CDCl3 400 MHz) d/ppm: 8.30 (s, 2H, N=C-H), 6.79-7.33 (m, 8H,H-benzene ring), 3.66-3.74 (m, 8H, O-(CH2)2-N=C). UV-Vis (k, nm): 268, 316.FT-IR (KBr m/cm-1): 1,637, m(C=N); 1,286, m(C-O-C); 3,458, m(OH) stretching frequency, respectively.

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

Reference:
Article; Wu, Huilu; Pan, Guolong; Bai, Yuchen; Wang, Hua; Kong, Jin; Shi, Furong; Zhang, Yanhui; Wang, Xiaoli; Research on Chemical Intermediates; vol. 41; 6; (2015); p. 3375 – 3388;,
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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 70627-52-0 as follows. 70627-52-0

General procedure: To a solution of [RhCl(cod)]2(2 mol %) in DMF at room temperature was added imine (1). Then, BF3¡¤Et2O (1.2 equiv) wasadded to the mixture and stirred for 30 min at the same temperature. Subsequently, 5,6-dihydro-2H-pyran-2-one (2, 1.2 equiv)was added to the mixture and then 1.0 MEt2Zn in hexane(3 equiv) was gradually added to the mixture at room temperature, and the mixture was stirred for 24 h. The mixture wasquenched with sat. NH4Cl and extracted with AcOEt. TheAcOEt layer was washed with sat. NaCl and dried over MgSO4.The solvent was removed in vacuo, and the residue was purified by column chromatography to give the corresponding antiazetidin-2-one.

According to the analysis of related databases, 70627-52-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Isoda, Motoyuki; Sato, Kazuyuki; Kunugi, Yurika; Tokonishi, Satsuki; Tarui, Atsushi; Omote, Masaaki; Minami, Hideki; Ando, Akira; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1608 – 1615;,
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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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, This compound has unique chemical properties. The synthetic route is as follows., 701-07-5

EXAMPLE 258A Preparation of 2-iso-propyloxybenzaldehyde The title compound was prepared as in Example 257A but employing 2-iso-propyloxybromobenzene in lieu of 1-bromo-3-isopropoxybenzene. Purification on silica, gel with 10% ether/hexane afforded the title compound (2.3 g, 70%). MS (DCI/NH3) m/z 165 (M+H)+, 182 (M+NH4)+.

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; Abbott Laboratories; US6284796; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20265-97-8, A common heterocyclic compound, 20265-97-8, name is 4-Methoxyaniline hydrochloride, molecular formula is C7H10ClNO, 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: Three stock solutions were prepared and connected to the flow reactor feed lines for Pumps A-C (see Figure 3 for a pictorial layout). Pump A delivered hydrochloric acid (0.84 M), Pump B a solution of aqueous sodium nitrite (0.98 M) and pump C delivered an aqueous solution of ascorbic acid (0.35 M). In addition a further pump was used to provide the solutions of aniline as their HCl salts dissolved in water (0.35 M). The entire reactor was maintained under positive internal pressure using a 75 psi back pressure regulator at the exit of the reactor. To initiate the reaction each flow channel was pumped at 0.5 mL/min. Progressing through the reactor; Channel A and B were mixed in a Uniqsis mixer chip of 0.27 mL internal volume (16 s residence time) before passing into a 2.75 mL PFA tubular residence coil (165 s residence time). The combined flow was then further united with the aniline solution mixing in a second Uniqsis mixer chip of 2 mL internal volume (80 s residence time). The reacting solution then passed into a 5 mL residence PFA foil coil (150 s residence time, the solution turns pale yellow to orange). The whole initial stage mixing unit was temperature regulated (10 C) using a Polar Bear Plus flow reactor unit. In the second stage reactor the freshly prepared diazonium mixture (combined flow rate 2 mL/min) was united at an Upchurch peek T-mixer with a solution of ascorbic acid delivered from Pump C set at 0.5 mL/min. The flow stream was then progressed into a 52 mL PFA flow coil (20.8 min residence time).The isolation of certain intermediate hydroxamic esters, namely 13-18, could be achieved by immediate extraction of the reactor output with ethyl acetate (5 volumes) and washing the organic phase with sodium hydrogen carbonate (2 M; 2). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to provide a pale yellow solid which was triturated with a 1:1 mixture of hexane and acetone to furnishing the desired product. Alternatively, the output solution was collected and left to stir for 1 h to ensure complete hydrolysis to the corresponding oxamic acid, 1-12, had occurred. The products were isolated by basification of the reaction mixture pH ~9 followed by extraction with EtOAc (3 volumes). The aqueous solution was then acidified to pH ~4 and extracted with EtOAc (3 volumes), the organic phase was dried over MgSO4, the solvent evaporated to yield compounds 1-12. Note: for compounds 1-12 a proton signal sites under the residual DMSO signal.

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

Reference:
Article; Hu, Te; Baxendale, Ian R.; Baumann, Marcus; Molecules; vol. 21; 7; (2016);,
Ether – Wikipedia,
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