Tag: M.W=100-200

461-82-5, The chemical industry reduces the impact on the environment during synthesis 461-82-5, name is 4-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

N-Bromosuccinamide (3.62 g, 20.34 mmol) was added to a solution of commercially available 4-(trifluoromethoxy)aniline (3.00 g, 1 6.95 mmol) in acetonitrile (30 mL) at 0C. The resulting mixture was allowed to warm to roomtemperature and stirred for 4 hours. The solvent was removed under reduced pressure to give the crude product which was purified by column chromatography eluting in 10% ethyl acetat/hexane to afford the title compound as brown oil (3.6 gm, 83%): 1 H NMR (400 MHz, CDCI3) oe: 4.11 (bs, 2 H), 6.73 (d, 1 H), 6.99 (dd, 1 H), 7.31 (d, 1 H). LC-Ms (m/z): [M-H] = 253.1.

The chemical industry reduces the impact on the environment during synthesis 461-82-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 437-83-2, name is 3-Fluoro-2-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 437-83-2, 437-83-2

NaNO2 (12.0 g, 1?73 mmol, in 40 m of water) solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 m of hydrobromic acid (4?7 %) and 100 m of water at -5 o Oc and stirred for 1 hour.This solution was then added slowly to the suspension of cuBr (45.2 g, 315 mmol) in 50 m of hydrobromic acid (4?7 %) at O Oc. The resulting mixture was stirred at o Oc for 1 hour then warmed to so Oc and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organie layer was washed with brine, dried oyer anhydrous Na2504 and concentrated to giye 1-bromo-3-fluoro-2-methoxybenzene.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

929-75-9, 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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 3-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-4-methyl-2H-chromen-2-one (19, 200 mg, 0.268 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 52 mg, 0.27 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (119 mg, 0.268 mmol), and the mixture was stirred at the same temperature for 2 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (20:1) to give the desired product 21c (84 mg, 34%). Mp 307.4+/-0.2 C; 1H NMR (500 MHz, DMF-d7): delta=8.93 (s, 1H), 8.06 (br t, J=5.8 Hz, 1H), 7.97 (s, 2H), 7.87 (s, 1H), 4.75 (t, J=7.0 Hz, 2H), 3.80 (t, J=5.8 Hz, 2H), 3.69 (s, 2H), 3.65-3.70 (m, 2H), 3.62-3.65 (m, 4H), 3.57-3.60 (m, 4H), 3.36 (q, J=5.8 Hz, 2H), 3.31 (t, J=5.8 Hz, 2H), 2.51 (s, 3H), 2.44-2.57 (m, 2H), 2.32-2.39 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=169.3, 161.2, 152.9, 149.2, 145.7, 134.2, 126.3, 122.9, 121.3, 120.8, 120.0, 112.4, 70.24, 70.16, 70.09, 70.07, 69.5, 67.1, 49.0, 39.9, 39.3, 27.7, 21.4, 14.9 ppm; IR (ATR, neat): nu=2927, 1703 (CO), 1654 (CO), 1614, 1561, 1200, 1146, 1113, 835 cm-1; MS (ESI): m/z: 920 [M+H+]; HRMS (EI): m/z calcd for C33H34F17N5O6: 919.2238 [M+]; [M+] not found.

The synthetic route of 1,11-Diamino-3,6,9-trioxaundecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

321-28-8, A common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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 solution of the selected anisole or biphenyl (13.0mmol) in 30mL of dry CH2Cl2 at 0 C, p-toluoylchloride (2g, 13.0mmol), and AlCl3 (3g, 22.05mmol) were added and the mixture was stirred at rt overnight. After addition of ice, the mixture was diluted with CH2Cl2, washed with NaHCO3 saturated solution, dried and evaporated to dryness.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gobbi, Silvia; Hu, Qingzhong; Foschi, Giacomo; Catanzaro, Elena; Belluti, Federica; Rampa, Angela; Fimognari, Carmela; Hartmann, Rolf W.; Bisi, Alessandra; Bioorganic Chemistry; vol. 86; (2019); p. 401 – 409;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

A 1 moles of a double-terminal amine polyether (structure of formula (2), R 2 = R 3 = H, n = 3), 18 moles of dichloroethane and 1 mole of sodium hydroxide (an aqueous solution having a concentration of 20% by weight) were charged into a reaction flask equipped with a cooling apparatus, 4 C, then slowly add 1 mole of acryloyl chloride, the temperature of the addition process does not exceed 15 C, after the addition of acryloyl chloride, the reaction is carried out at 15 C for 3 hours; the resulting reaction is allowed to stand and the organic phase is separated, Washed with saturated aqueous NaCl solution 3 times, dried with anhydrous sodium sulfate, the organic solvent was distilled off to obtain a crude product of orange-red viscous liquid, and the crude product was washed with acetone to obtain the product of polymerization grade. The product of the polymerization stage was confirmed to be a monomer represented by the formula (1) (wherein Ri = R2 = R3 = H, n= 3) using an infrared spectrum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; CHINA PETROLEUM & CHEMICAL CORPORATION;.; DRILLINGRESEARCH INSTITUTE OF SINOPEC ZHONGYUAN PETROLEUM ENGINEERING CO., LTD; WANG, ZHONGHUA; (12 pag.)CN104926678; (2017); B;,
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,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

24332-20-5, The chemical industry reduces the impact on the environment during synthesis 24332-20-5, name is 1,1,2-Trimethoxyethane, I believe this compound will play a more active role in future production and life.

Example 10 A flask was charged with methoxyacetaldehyde dimethylacetal (1.2 equiv.), trifiuoroacetic acid (1.3 equiv.), and water (equal volume to TFA), and the mixture was stirred at 50 C for 10 min. The reaction mixture was then removed from the heating bath and TEA (1.3 equiv.) was added followed by a solution of 3-(N-Boc-aminomethyl)-azetidine (1 equiv.) in EtOH and DCM, and then NaBH(OAc)3 (3 equiv.). The reaction was stirred for 12 hrs at 20 C. The reaction mixture was extracted and distilled to remove some ethanol. To the organic layer was added 5M HC1 in iPrOH (7 equiv.) at 50 C. TBME was added at 48 C over 45 min, and cooled to 20 C over 60 min. The reaction stirred for another 60 min, filtered, and the filter cake was washed with TBME. The organic layer was dried to provide l-(2-methoxyethyl)-3- (methylamino)-azetidine dihydrochloride.

The chemical industry reduces the impact on the environment during synthesis 1,1,2-Trimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SATORI PHARMACEUTICALS, INC.; BRONK, Brian, Scott; AUSTIN, Wesley, Francis; CREASER, Steffen, Phillip; FULLER, Nathan, Oliver; HUBBS, Jed, Lee; IVES, Jeffrey, Lee; SHEN, Ruichao; WO2013/36669; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem