Category: ethers-buliding-blocks

Synthetic Route of 767-91-9, 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 767-91-9 as follows.

General procedure: The arylalkyne 1,acetic anhydride (Ac2O), and an anhydrous solvent were added to a dried three-necked flask under argon atmosphere and the mixture was stirred for 30 min at room temperature. Further, HCl(g)prepared using H2SO4 and NaCl at 160 8C was added to the mixture through the rubber tube until the starting material conversed completely, monitored by TLC, and the unreacted HCl(g) was absorbed by aqueous NaOH. The solvent was removed and the residue was purified using flash chromatography on a silica gel.

According to the analysis of related databases, 767-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Cai-Xia; Ma, Cun-Hua; Xiao, Fu-Rong; Chen, Hong-Wei; Dai, Bin; Chinese Chemical Letters; vol. 27; 11; (2016); p. 1683 – 1685;,
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Reference of 70384-51-9,Some common heterocyclic compound, 70384-51-9, name is Tris(2-(2-methoxyethoxy)ethyl)amine, molecular formula is C15H33NO6, 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.

Synthesis of AMPS-ammonium salt monomer. A nitrogen purged 50 ml schlenk flask was charged with freshly distilled tris[2-(2-methoxyethoxy)-ethyl]amine (1.69 g, 5.24 mmol) and 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) (1.09 g, 5.24 mmol) and stirred at ambient temperature for 8 hr or until completely dissolved. Total dissolution completes formation of the AMPS-ammonium salt monomer as a transparent light amber oil in a 99percent yield which was used immediately without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Tris(2-(2-methoxyethoxy)ethyl)amine, its application will become more common.

Reference:
Patent; The Government of the US, as represented by the Secretary of the Navy; US2008/51605; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1706-12-3, name is 1-Methyl-4-phenoxybenzene, 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 1706-12-3, Recommanded Product: 1706-12-3

(b) 4-(4-Methylphenoxy)benzenesulfonyl chloride To a solution of 1.84 g (10.0 mmol) of 4-methyldiphenyl ether (see J. Chem Soc., Perkin Trans. 1, 1992, 407-408) with 2 mL of dichloromethane in an ice-bath was added a solution of chlorosulfonic acid (0.73 mL, 11.0 mmol) in 2 mL of dichloromethane dropwise. The resulting mixture was stirred at 0 C. to room temperature for 2 hours, and then oxalyl chloride (11.14 mL, 13.0 mmol) was added dropwise, followed by 0.15 mL of DMF. The resulting mixture was heated to 40 C. for 1 hour and then allowed to cool to room tempereature over a 2 hour period. The reaction mixture was poured into ice-pH 7 phosphate buffer (50 mL), then extracted with EtOAc:Hexane (4:3) (3*150 mL). The combined organic layers were washed with brine (75 mL). The aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL). The organic layer was dried over Na2 SO4, then evaporated by vacuum to give crude product as white solid. This solid was triturated with hexane and collected by filtration, then dried under high vacuum to give 1.555 g (57%) of 4-(4-methylphenoxy)benzenesulfonyl chloride as white solid: mp 295-300 C. 1 H-NMR (DMSO-d6) delta2.34 (s, 3H), 6.91-6.99 (dd, J=7.7,8.4 Hz, 4H), 7.24-7.27 (d, J=8.4 Hz, 2H), 7.61-7.63 (d, J=8.1 Hz, 2H). Anal. calc. for C13 H11 O3 SCl: C, 55.22; H, 3.92; S, 11.34; Cl, 12.71. Found: C, 55.06; H, 3.95; S, 11.28; Cl, 12.71.

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-Methyl-4-phenoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US6153757; (2000); A;,
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Reference of 20059-73-8, A common heterocyclic compound, 20059-73-8, name is 2-(4-(Aminomethyl)phenoxy)-N,N-dimethylethanamine, molecular formula is C11H18N2O, 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.

Example 6 N-[4-[2-(Dimethylamino)ethoxy]benzyl]-2-methoxy-5-sulfamoylbenzamide To a cooled suspension of 14.3 g of 2-methoxy-5-sulfamoylbenzoic acid in 60 ml of tetrahydrofuran were successively added dropwise 6.25 g of triethylamine and 7.45 g of pivaloyl chloride with stirring. The mixture was stirred at the same temperature for 1 hour and then a solution of 10.0 g of 4-[2-(dimethylamino)ethoxy]-benzylamine in 40 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 14 hours and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate to give a precipitate, which was washed with water and ethyl acetate, of 16.6 g of colorless crystals. Recrystallization of the crystals from ethanol gave the title compound as colorless needles, m.p. 154-155C. Analysis for C19H25N3O5S:

The synthetic route of 20059-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hokuriku Pharmaceutical Co.,Ltd; EP306827; (1991); B1;,
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These common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, 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. Safety of 1-Bromo-3-methoxypropane

Into a 250-mL 3-necked round-bottom flask, was placed a solution of methyl 3- chloro-4-hydroxybenzoate (10.0 g, 53.59 mmol, 1.00 equiv) in N,N-dimethylfonnamide (100 mL), 1-bromo-3-methoxypropane (12.3 g, 80.38 mmol, 1.50 equiv), potassium carbonate (22.3 g, 161.35 mmol, 3.00 equiv). The resulting solution was stirred for 3 h at 50 C. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×70 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of water and lxlOO mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2). This resulted in 13.1 g (94%) of methyl 3-chloro-4-(3- methoxypropoxy)benzoate as a orange solid. ?H NMR: PHNW-1-2-1 (300 MHz, DMSO) 7.91-7.87 (m, 2H), 7.25 (d, J= 8.4 Hz, 1H), 4.19 (t, J= 6.0 Hz, 2H), 3.86 (s, 3H), 3.50 (t, J=6.3 Hz, 2H), 3.25 (s, 3H), 2.04-2.00 (m, 2H).

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

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (81 pag.)WO2018/22282; (2018); A1;,
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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. 2216-69-5, name is 1-Methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: 1 mL [Bmim]NO3, 0.5 mmolsubstrate and 0.25 mmol Br2 were added to a dried 45 mL tube equipped witha magnetic stirring (note: the air in the tube was not removed). Then thereaction tube was sealed to perform the reaction at 80 C for 24 h. Once thereaction time was reached, the mixture was cooled to room temperature and3 mL water was added. Then the desired product was extracted with CH2Cl2(3 10 mL). GC analysis of the mixture provided the GC yield of the product.The product in another parallel experiment was purified by columnchromatography, and identified by 1H NMR and 13C NMR.

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 2216-69-5.

Reference:
Article; Ren, Yun-Lai; Wang, Binyu; Tian, Xin-Zhe; Zhao, Shuang; Wang, Jianji; Tetrahedron Letters; vol. 56; 46; (2015); p. 6452 – 6455;,
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Reference of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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.

EXAMPLE III To a stirred and cooled (water-bath) suspension of 7 parts of a sodium hydride dispersion 78% and 75 parts of dimethylsulfoxide is added dropwise, during a 30 minutes-period, a solution of 37 parts of 2,4-dichlorobenzeneacetonitrile in 100 parts of dimethylsulfoxide. The whole is stirred for 30 minutes while cooling in a water-bath. Then there is added dropwise, during a 30 minutes-period, a solution of 56 parts of 1-bromo-4-(2-bromoethoxy)benzene in 125 parts of dimethylsulfoxide and stirring is continued for another 30 minutes. The reaction mixture is poured onto water and the product is extracted twice with 2,2′-oxybispropane. The combined extracts are washed twice with water, dried, filtered and evaporated. The residue is triturated in petroleumether. The product is filtered off and crystallized from ethanol, yielding 38 parts of alpha-[2-(4-bromophenoxy)ethyl]-2,4-dichlorobenzeneacetonitrile; mp. 73.9 C.

Statistics shows that 1-Bromo-4-(2-bromoethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 18800-30-1.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4598085; (1986); A;,
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16452-01-0, name is 3-Methoxy-4-methylaniline, 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. HPLC of Formula: C8H11NO

General procedure: 1,3-bis(3,4-dichlorophenyl)urea (1). 3,4-dichlorophenylisocyanate (200 mg, 1.064 mmol) and 3,4-dichloroaniline (172 mg, 1.064 mmol) were dissolved in 10 mL of anhydrous dioxane. The reaction mixture was warmed to 55 C, stirred under nitrogen over night and then cooled to room temperature (RT). The solvent was removed under vacuum and the crude was crystallized twice in ethyl acetate/hexane to afford 1 (181 mg, 49%).

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Denoyelle, Severine; Chen, Ting; Chen, Limo; Wang, Yibo; Klosi, Edvin; Halperin, Jose A.; Aktas, Bertal H.; Chorev, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 402 – 409;,
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Reference of 6443-69-2,Some common heterocyclic compound, 6443-69-2, name is 1,2,3-Trimethoxy-5-methylbenzene, molecular formula is C10H14O3, 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: BF3¡¤Et2O was slowly added dropwise, to a stirred solution of polyhydroxy or polymethoxy phenols and alkyl alchol in dioxane at 0C. After the addition was completed, the stirring was continued for 3h at room temperature. The mixture was poured water and extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure. The crude was chromatographed on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,3-Trimethoxy-5-methylbenzene, its application will become more common.

Reference:
Article; Kamauchi, Hitoshi; Oda, Takumi; Horiuchi, Kanayo; Takao, Koichi; Sugita, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
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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 910251-11-5 as follows. Application In Synthesis of Potassium trifluoro(methoxymethyl)borate

1006241 Step B: Preparation of 2-ethoxy-5-(methoxymethyl)benzonitrile: A heavy walled pressure tube was charged with 5-bromo-2-ethoxybenzonitrile (0.500 g, 2.21 mmol), 8mls of dioxane and 2mls of water. Potassium methoxymethyltrifluoroborate (0.672 g, 4.42 mmol), PdCZ2(dppf) dichloromethane adduct (0.361 g, 0.442 mmol), and cesium carbonate (2.16 g, 6.64 mmol) were then added to the reaction mixture under a nitrogen atmosphere, the tube was sealed and heated to 100 C for 16 hours. After allowing to cool to ambient temperature, the mixture was diluted with EtOAc/water and filtered through GF/F filter paper. The organic layer was isolated from the filtrate, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography to give 2-ethoxy-5-(methoxymethyl)benzonitrile (0.100 g, 24% yield).

According to the analysis of related databases, 910251-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; BLAKE, James F.; BRANDHUBER, Barbara J.; HAAS, Julia; NEWHOUSE, Brad; THOMAS, Allen A.; WINSKI, Shannon L.; WO2014/78331; (2014); A1;,
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