Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, 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 4463-59-6, Recommanded Product: 1-(2-Bromoethoxy)-2-methoxybenzene

EXAMPLE 68 1-[2-(2-Methoxyphenoxy)ethyl]-4-benzamidopiperidine 2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heated on a steam bath for 4 hr. The resultng mass was crushed and stirred in water (200 ml.) at 60 for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4. Analysis: Found: C, 64.74; H, 7.08; N, 7.14. C21 H26 N2 O3.HCl requires C, 64.52; H, 6.96; N, 7.17%.

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; John Wyeth & Brother Limited; US4029801; (1977); A;,
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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. 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 14804-31-0

After starting the Grignard reaction by adding 25.0 ml 4-bromo2-methyl-anisole to a mixture of 30.2 g (1.24 mol) magnesium turnings and 650 ml THF, 150 ml 4-bromo2-methylanisole (total: 175.0 ml were added at a pace sufficient to maintain reflux temperature. The reaction mixture was heated to reflux for additional 5 h, cooled to r.t. and dropped at 0 C. within 1 h to a stirred solution prepared by mixing 904 g (500 ml, 4.19 mol) 1,4-dibromo-butane in 1000 ml THF with a freshly prepared solution of 1.28 g (60.0 mmol) LiCl and 4.00 g (29.8 mmol) Cu(II)Cl2 in 140 ml THF. Stirring was continued for 12 h at r.t. followed by the addition of 400 ml of a 20% ammonium chloride solution and 200 ml ethyl acetate. The water phase was extracted twice with 250 ml ethyl acetate, all organic phases were combined, dried over sodium sulphate and evaporated. The resulting oil was fractionated by vacuum distillation. Yield: 226.3 g (71%), b.p. 131-134 C./0.01 mbar. 1H-NMR(400 MHz, D6-DMSO): delta=1.60(quintet, 2H, C2-CH2-Ph), 1.82(quintet, 2H, C2-CH2-Br), 2.23(s, 3H, CH3), 2.51(t, 2H, CH2-Ph), 3.55(t, 2H, CH2-Br), 3.70(s, 3H, OCH3), 6.67d, 1H, 5-H), 6.72(s, 1H, 3-H), 7.01(d, 1H, 6-H).

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 14804-31-0.

Reference:
Patent; Hofmeister, Thomas; Reiff, Ulrike; von Hirschheydt, Thomas; Voss, Edgar; US2006/69095; (2006); A1;,
Ether – Wikipedia,
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Some common heterocyclic compound, 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline, molecular formula is C9H13NO2, 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. category: ethers-buliding-blocks

The synthetic procedure used in this preparation is outlined in Scheme M. 4-(4-Fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (180 mg), 4,5-dimethoxy-2-methyl-phenylamine (86 mg) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 265 mg) were dissolved in 10 mL DMF, followed by 0.2 mL di-iso-propylethyl amine. The mixture was heated at 50 for 72 hours, then cooled, diluted with aqueous pH 2 buffer and ethyl acetate, and the layers separated. The organic layer was washed with saturated sodium bicarbonate and brine, then dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed in 3% MeOH/DCM. The fraction containing the product was washed with 10% aqueous HCl, and concentrated in vacuo to yield 52 mg of 4-(4-fluoro-phenyl)-1-(2-hydroxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid (4,5-dimethoxy-2-methyl-phenyl)-amide, MS (M+H)=430.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41864-45-3, its application will become more common.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; Walker, Keith Adrian Murray; US2011/28502; (2011); A1;,
Ether – Wikipedia,
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Electric Literature of 67191-35-9,Some common heterocyclic compound, 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, molecular formula is C11H14O, 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.

EXAMPLE 1 Metathesis by Ethenolysis of Methyl Oleate Catalyzed by a Type 3 Complex (FIG. 1) in an Ionic Liquid; 1 ml of 3-butyl-1,2-dimethylimidazolium bis-triflylamide with formula [BMMI]+[N(CF3SO2)2]- pre-dried overnight at 80 C., 148 mg of methyl oleate (source: Fluka, with a purity higher than 98%) and 15 mg of the complex with formula Cl2Ru(CH-o-O-iPrC6H4)PCy3 (synthesized by reacting the 1st generation Grubbs complex with formula Cl2Ru(CHC6H5)(PCy3)2 with 1-isopropoxy-2-vinylbenzene in the presence of CuCl), this corresponding to 5% molar of catalyst with respect to methyl oleate, were introduced, in an inert atmosphere of argon, into an autoclave reactor provided with an agitation system and a pressure sensor. The autoclave was then placed under vacuum and pressurized to obtain a pressure of 10 bars (1 MPa) of ethylene (origin: Alphagas, quality N25). The temperature was kept constant at 20 C. The medium was stirred at ambient temperature for 2 hours, then the excess ethylene was slowly purged by returning to atmosphere pressure at a temperature not exceeding 20 C. and the autoclave was again placed under an atmosphere of argon. The products were separated from the ionic liquid by adding 2 to 3 ml of heptane distilled over CaH2 and degassed. An aliquot (100 mul) of the extracted solution was passed through a short silica column (2 cm) eluted with diethyl ether. It was analyzed by gas phase chromatography (ZB-1 column, 100% dimethylpolysiloxane, 30 metres, helium vector gas 2 ml/min, temperature programming: 60 C. then 5 C./min to 220 C.) coupled to a mass spectrometer. The methyl oleate conversion was 95%. It was calculated using decane as an internal reference. The reaction products were composed of 1-decene (fraction A) and methyl decenoate (fraction B). The presence of 1-decene isomers was not detected. Homo-metathesis products were present in trace amounts and could not be quantified.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropoxy-2-vinylbenzene, its application will become more common.

Reference:
Patent; Olivier-Bourbigou, Helene; Vallee, Christophe; Hillion, Gerard; US2007/179307; (2007); A1;,
Ether – Wikipedia,
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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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H10N2O

To a 40% aqueous sodium hydrogen sulfite solution (10 mL) was added 4-fluorobenzaldehyde (1.45 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added a solution of 3-methoxybenzene-1,2-diamine (1.7 g) in EtOH (45 mL), and the mixture was stirred for 2 hours under heating to reflux. Water was added to the reaction solution, and the mixture was stirred at room temperature for 10 minutes. Then, the precipitate was filtered and the resulted solid was washed with Et2O to give 2-(4-fluorophenyl)-4-methoxy-1H-benzimidazole (2.38 g).

According to the analysis of related databases, 37466-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KAWANO, Yoshikazu; SHIMIZU, Hiroshi; ISHIKAWA, Shunpei; TAKEMURA, Isso; HARIGUCHI, Norimitsu; MATSUBA, Miki; MATSUMOTO, Makoto; (92 pag.)US2019/40039; (2019); A1;,
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Related Products of 50868-73-0,Some common heterocyclic compound, 50868-73-0, name is 2-Methoxy-6-methylaniline, molecular formula is C8H11NO, 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.

[1893] A solution of 2-methoxy-6-methylaniline (4 equivalents) in dichloromethane (0.2 M) was treated with pyridine (8 equivalents) followed by bromoacetyl chloride (1 equivalent). After 3 hours at room temperature, the mixture was treated with sodium carbonate (12 equivalents) and the product from Example 119A (3 equivalents) in dioxane:water (2:1). The heterogeneous mixture was heated to 40 C. overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and the residue triturated with 5% methanol:dichloromethane. The solid inorganic material was filtered and the filtrated concentrated and purified by HPLC. Isolated as an acetate salt. (45 mg, 44%). 1H NMR (300 MHz, DMSO-d6) delta1.71 (m, 2H), 1.99 (m, 4H), 2.15 (m, 3H), 2.30 (m, 2H), 3.10 (m, 1H), 3.15 (s, 2H), 3.75 (s, 3H), 6.86 (dd, J=9, 1.5 Hz, 2H), 7.16 (t, J=9 Hz, 1H), 7.30 (m, 2H), 7.45 (m, 1H), 8.26 (dd, J=4.5, 1.5 Hz, 1H), 8.95 (s, 1H); MS (DCI/NH3) m/e 340 (M+H-16)+; 356 (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 2-Methoxy-6-methylaniline, its application will become more common.

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.; US2003/229094; (2003); A1;,
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24599-58-4, name is 2,5-Dimethoxytoluene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 24599-58-4

2-Methyl-1,4-bis(methyloxy)benzene (6.12 g, 40 mmol) was dissolved in acetic acid (20 mL) and heated at 40 C. A solution of nitric acid (4.32 g) in acetic acid (10 mL) was added to above solution drop wise over 5 minutes. The reaction mixture was stirred at 40 C. for 30 min (yellow precipitates formed), then room temperature for 30 min and then diluted with water (300 mL). The precipitate was collected by filtration, washed with water, and dried in the air for 16 h to afford the title compound (7.56 g, 96%) as a yellow solid. MS (ES) m/e 198 [M+H]+.

The synthetic route of 24599-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goodman, Krista B.; Neeb, Michael J.; Sehon, Clark A.; Viet, Andrew Q.; Wang, Gren Z.; US2008/21023; (2008); A1;,
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Some common heterocyclic compound, 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, molecular formula is C20H16FNO, 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. Application In Synthesis of N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline

Step 1): To a solution of (S)-4-phenyl-2-oxazolidinone (41 g, 0.25 mol) in CH2Cl2 (200 mL), was added 4-dimethylaminopyridine (2.5 g, 0.02 mol) and triethylamine (84.7 mL, 0.61 mol) and the reaction mixture was cooled to 0 C. Methyl-4-(chloroformyl)butyrate (50 g, 0.3 mol) was added as a solution in CH2Cl2 (375 mL) dropwise over 1 h, and the reaction was allowed to warm to 22 C. After 17 h, water and H2SO4 (2N, 100 mL), was added the layers were separated, and the organic layer was washed sequentially with NaOH (10%), NaCl (sat’d) and water. The organic layer was dried over MgSO4 and concentrated to obtain a semicrystalline product. Step 2): To a solution of TiCl4 (18.2 mL, 0.165 mol) in CH2Cl2 (600 mL) at 0 C., was added titanium isopropoxide (16.5 mL, 0.055 mol). After 15 min, the product of Step 1 (49.0 g, 0.17 mol) was added as a solution in CH2Cl2 (100 mL). After 5 min., diisopropylethylamine (DIPEA) (65.2 mL, 0.37 mol) was added and the reaction mixture was stirred at 0 C. for 1 h, the reaction mixture was cooled to -20 C., and 4-benzyloxybenzylidine(4-fluoro)aniline (114.3 g, 0.37 mol) was added as a solid. The reaction mixture was stirred vigorously for 4 h at -20 C., then acetic acid was added as a solution in CH2Cl2 dropwise over 15 min, the reaction mixture was allowed to warm to 0 C., and H2SO4 (2N) was added. The reaction mixture was stirred an additional 1 h, the layers were separated, washed with water, separated and the organic layer was dried. The crude product was crystallized from ethanol/water to obtain the pure intermediate. Step 3): To a solution of the product of Step 2 (8.9 g, 14.9 mmol) in toluene (100 mL) at 50 C., was added N,O-bis(trimethylsilyl)acetamide (BSA) (7.50 mL, 30.3 mmol). After 0.5 h, solid TBAF (0.39 g, 1.5 mmol) was added and the reaction mixture stirred at 50 C. for an additional 3 h. The reaction mixture was cooled to 22 C., CH3OH (10 mL), was added. The reaction mixture was washed with HCl (1 N), NaHCO3 (1 N) and NaCl (sat’d.), and the organic layer was dried over MgSO4. Step 4): To a solution of the product of Step 3 (0.94 g, 2.2 mmol) in CH3OH (3 mL), was added water (1 mL) and LiOH.H2O (102 mg, 2.4 mmole). The reaction mixture was stirred at 22 C. for 1 h and then additional LiOH.H2O (54 mg, 1.3 mmole) was added. After a total of 2 h, HCl (1 N) and EtOAc was added, the layers were separated, the organic layer was dried and concentrated in vacuo. To a solution of the resultant product (0.91 g, 2.2 mmol) in CH2Cl2 at 22 C., was added ClCOCOCl (0.29 mL, 3.3 mmol) and the mixture stirred for 16 h. The solvent was removed in vacuo. Step 5): To an efficiently stirred suspension of 4-fluorophenylzinc chloride (4.4 mmol) prepared from 4-fluorophenylmagnesium bromide (1 M in THF, 4.4 mL, 4.4 mmol) and ZnCl2 (0.6 g, 4.4 mmol) at 4 C., was added tetrakis(triphenyl-phosphine)palladium (0.25 g, 0.21 mmol) followed by the product of Step 4 (0.94 g, 2.2 mmol) as a solution in THF (2 mL). The reaction was stirred for 1 h at 0 C. and then for 0.5 h at 22 C. HCl (1 N, 5 mL) was added and the mixture was extracted with EtOAc. The organic layer was concentrated to an oil and purified by silica gel chromatography to obtain 1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-3(R)-(3-oxo-3-phenylpropyl)-2-azetidinone: HRMS calc’d for C24H19F2NO3=408.1429, found 408.1411.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 70627-52-0, its application will become more common.

Reference:
Patent; Veltri, Enrico P.; US2006/69080; (2006); A1;,
Ether – Wikipedia,
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Synthetic Route of 36805-97-7, The chemical industry reduces the impact on the environment during synthesis 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, I believe this compound will play a more active role in future production and life.

3-Hydroxy phenyl acetic acid-t-butyl ester (Reagent F) A stirred suspension of 3-hydroxy-phenyl acetic acid (1.52 g, 10 mmol) in anhydrous toluene (20 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (9.6 mL, 40 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. The residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (1.17 g, 56%). 1H-NMR (300 MHz, CDCl3): delta1.47(s, 9H), 3.49(s, 2H), 6.30(s, 1H), 6.70-6.79 (m, 2H), 6.81(d, J=7.6 Hz, 1H), 7.16(t, J=7.7 Hz, 1H).

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, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
Ether – Wikipedia,
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Related Products of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Hereinafter, sometimes, referred to as the compound (1).) Preparation Mg 165 mg of (2.0 eq) and charged with THF 10 mL reactor under a nitrogen atmosphere, 2-bromo-5-methoxy-toluene 1.37g of (2.0 eq) in addition, the mixture was stirred for 5 hours at 60 . The reaction mixture was cooled in an ice bath, was obtained according to Example 1-2 3,6-bis {[t-butyl (dimethyl) silyl] oxy}-9H-xanthene-9-one 1.50g of (3.40 mmol) It was added dropwise a THF solution 10 mL, and stirred for 30 minutes and returned to room temperature. Then, slowly adding 2N aqueous hydrochloric acid 20mL the reaction mixture under ice-cooling, followed by stirring at room temperature for 15 hours, added with chloroform, the organic layer was separated, saturated aqueous NaHCO3, washed sequentially with saturated aqueous sodium chloride solution. After drying over MgSO4, washing the crystalline residue obtained and the solvent was evaporated under reduced pressure with diethyl etherBy to give 6-hydroxy-9- (4-methoxy-2-methylphenyl)-3H-xanthene-3-one 0.77g (68% yield) as an orange crystals.

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-4-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; HARADA, KOICHIRO; TAKAKU, TOMOYUKI; TAKEUCHI, HAYATO; (13 pag.)JP2015/205841; (2015); A;,
Ether – Wikipedia,
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