Month: June 2021

Application of 16452-01-0, A common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.

Reference Production Example 79 (1473) A mixture of 6.85 g of 3-methoxy-4-methylaniline and 150 mL of chloroform was cooled to 0 C. and 26.5 g of tetrabutylammonium tribromide was added, followed by stirring at the same temperature for 20 minutes. To the reaction mixture, chloroform was added. The organic layer was washed with a sodium bicarbonate solution, an aqueous sodium sulfite solution, water, and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. (1474) The residue thus obtained was subjected to silica gel column chromatography to obtain 7.85 g of 2-bromo-5-methoxy-3-methylalanine. (1475) 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.76 (3H, s), 3.93 (2H, br s), 6.28 (1H, s), 7.12 (1H, s).

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; AZUMA, Shuhei; ARIMORI, Sadayuki; MAEHATA, Nao; (235 pag.)US2016/150787; (2016); A1;,
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Application of 886762-08-9, 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5-bromo-2-(trifluoromethoxy)aniline (2 g, 7.8 mmol), K2CO3 (2.7 g, 19.5 mmol), and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (50% in THF, 4.4 mL, 15.6 mmol) in dioxane (60 mL) was degassed for 20 min with N2. PdCl2(dppf)- CH2Cl2 (319 mg, 0.39 mmol) was added and the mixture was further degassed for 10 min then heated to 100 oC for 1 h. The reaction mixture was cooled to rt, filtered through a pad of celite, concentrated, and purified by chromatography (EA/hexane) to provide 1.49 g (74%) of Intermediate 44A. LCMS [m/z] calculated for C8H8F3NO: 191.1 found 192.2[M+H]+, tR=4.22 min (Method 4).

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; YEAGER, Adam; TURNBULL, Philip; ZHANG, Lin; FAN, Junhua; TAMIYA, Junko; STEINBERG, Marcos; FOWLER, Tom; BENELKEBIR, Hanae; PASCERI, Raffaele; IEVA, Maria; GRANT, Kevan; TRAN, Yang; (403 pag.)WO2018/45246; (2018); A1;,
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Reference of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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: The reaction mixture containing 0.5 g (1.8 mmol) of 4-(dibromomethyl)benzenecarbaldehyde (7), 0.11 g (0.0018 mmol) of isopropylamine (12) and 0.2 g of molecular sieves 3 A in 10 mL of dry benzene was thermostated at room temperature for 24 h. N-Isopropyl-4-(dibromomethyl)benzenecarbimine (14) (0.44 g, 77%) in the form of yellow oil was obtained by filtration through the molecular sieves followed by the removal of the solvent in vacuo provided by water jetpump.

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

Reference:
Article; Gazizov; Ivanova, S. Yu.; Karimova; Bagauva; Gazizova; Karimova; Russian Chemical Bulletin; vol. 65; 1; (2016); p. 191 – 194; Izv. Akad. Nauk, Ser. Khim.; 1; (2016); p. 191 – 194,4;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 103-50-4, name is Benzyl ether, A new synthetic method of this compound is introduced below., COA of Formula: C14H14O

6-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester (4). Substantially monodispersed benzyl ether 3 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filtered through Celite 545 to remove the catalyst, and the filtrate was concentrated in vacuo to yield the monodispersed compound 4 as a clear oil (0.67 g, 79%). FAB MS: m/e 425 (M+H), 447 (M+Na).

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nobex Corporation; US6867183; (2005); B2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7664-66-6, name is 4-Isopropoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Isopropoxyaniline

A mixture of 4-bromo-2-fluoro-l-nitrobenzene (0.39, 1.36 mmol), 4-(propan-2-yloxy)aniline (0.229,1 .43 mmol) and K2C03 (0.38 g, 2.73 mmol) in DMF (3 mL) was stirred at 90 C for 5h. Then thereaction mixture was diluted with EtOAc and washed with 5% aq. LiCI solution. The organic phasewas dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 columnchromatography (hexanes I EtOAc from 30:1 to 20:1) to give 0.43g (90%) of the product as orangesolid.1H NMR (500 MHz, CDCI3) O 9.37 (5, 1H), 8.04 (d, 1H), 7.12-7.17 (m, 3H), 6.93-6.97 (m, 2H), 6.81 (dd, 1H), 4.56 (sep, 1H), 1.36 (d, 6H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ARISAN THERAPEUTICS INC.; PLEWE, Michael; BROWN, Eric; GANTLA, Vidyasagar; HENKEL, Gregory; MCCORMACK, Kenneth; SOKOLOVA, Nadzeda V.; SHIN, Young-Jun; (147 pag.)WO2018/13430; (2018); A2;,
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Application of 707-07-3, 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 707-07-3 as follows.

4-Methylbenzenesulfonic acid (3.1 g, 16 mmol) was converted to N1-benzyl-4-bromobenzene-1,2-diamine (45 g, 160 mmol).And 500 mL of dichloromethane and o-trimethyl benzoate30 mL is added to the mixed solution and reacted for about 40 hours at room temperature under nitrogen. After the reaction was completed, the organic layer was concentrated under reduced pressure, washed with 40% methanol / water and sodium hydrogencarbonate / water, and dried to obtain a product. (22.3 g, yield 40%)

According to the analysis of related databases, 707-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SFC Ltd.; Ryu Se-jin; Sim So-yeong; Lee Sang-hae; (51 pag.)KR102030388; (2019); B1;,
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These common heterocyclic compound, 538-86-3, name is (Methoxymethyl)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. SDS of cas: 538-86-3

Commercially available from Sigma-Aldrich is benzyl methyl ether, PhCH2OCH3. To 100 ml of diethyl ether in a Parr pressure vessel, 3.62 g (0.032 moles) of potassium t-butoxide is added with stirring. To this suspension 2 ml (0.016 moles) of benzyl methyl ether is slowly added. Oxygen is removed from the flask by alternating cycles (10) of inert gas pressurization and venting. The stirred solution is then exposed to 80 psi NO gas at room temperature for 24 hours. When the reaction is complete, i.e. no more NO gas was consumed, then the head space is purged of NO gas and the tan solid filtered and washed with ether. The UV-vis spectrum of this material has a peak at 258 nm and it yields a positive Greiss reaction. The crude tan product is analyzed for NO release. A solution is made of 6.7 mg of the tan product in 0.1 ml of 10 mM NaOH. In a reactor vessel containing 3 ml of pH 7.4 buffer is injected the 0.1 ml of the tan product solution. The tan product generates 0.13 mg of NO over a 79 minute time period.

The synthetic route of (Methoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arnold, Ernst V.; Doletski, Blaine G.; Raulli, Robert E.; US2005/203069; (2005); 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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 93919-56-3

To a solution of lithium 1 -methyl-3 -(4-methyl-piperazin- 1 -yl)- lH-indazole-6- carboxylate (88mg, 0.32 mmol) in anhydrous DMF (5mL) was added EDC (73mg, 0.38mmol) and etaOBt (51mg, O.38mmol). The mixture was stirred for 10 min. then Et3N (0.1 ImL, 0.80mmol) and 4-trifluoromethoxybenzylamine (O.O58mL, 0.38 mmol) were added. The mixture was heated at 50 0C for 15 hr. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (25 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography on silica yielded the title compound (28mg, 20%). m/z (M+eta) = 448.46

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 93919-56-3.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61109; (2008); A2;,
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20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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. Formula: C8H9BrO2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 C. and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted, DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed through a through a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100% ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70% purity). MS (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)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 60876-70-2, Quality Control of 1-Bromo-4-(tert-butoxy)benzene

Synthesis of (4-tert-butoxy-phenylethynylVtrimethyl-silane (2). A 20 mL microwave tube was charged with a mixture of 1 -bromo-4-tert- butoxybenzene 1 (1.0 g, 4.36 mmol), PdCl2(dppf) (71 mg, 0.087 mmol), CuI (33 mg,0.174 mmol), DIPA (0.924 mL, 6.55 mmol), and THF (15 mL). Tube was backfilled with nitrogen, sealed, and irradiated in a microwave reactor (max. power 250W) at 100C for 5 min. Solution was diluted with water (200 mL) and extracted with EtOAc (3 x 80 mL). Combined organic layers were washed with water (1 x 100 mL) and brine (1 x 80 mL), dried (Na2SO4), filtered and concentrated in vacuo. Crude product was purified by normal phase flash chromatography (40 g SiO2, 0-30% EtO Ac/Hex) to provide the desired compound 2 (488 mg, 45%) as a clear colorless oil. LC-MS: [M+H]+= Not observed; Ret. Time (Method A) 7.87 min; 1H NMR (250 MHz, CDCl3) delta 0.2 (s, 9H), 1.3 (s, 9H), 6.9 (d, 2H), 7.4 (d, 2H).

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-(tert-butoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHAOGEN, INC.; WO2008/154642; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem