Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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 7252-83-7, Recommanded Product: 2-Bromo-1,1-dimethoxyethane

To a mixture of 4-chloro-6-aminobenzene-1,3-disulfonamide (Aldrich, 15.2 g, 53.3 mmol) and bromoacetaldehyde dimethylacetal (6.3 mL, 9 g, 53.3 mmol) in anhydrous dioxane (45 mL) at 120 C., was added dropwise 48% hydrobromic acid in H20 (2 mL). The mixture was then heated at 100 C. for 20 minutes. The residue, after evaporation of the solvent, was diluted with water, the resultant precipitate was filtered, washed with water to give a sticky solid that was dissolved in EtOAc and dried over Na2SO4. The residue after evaporation of the solvent was recrystallized from EtOAc/hexane to give the title compound in quantitative yield as a white solid: mp 203-205 C.; 1H NMR (400 MHz, d6-DMSO) delta 8.16 (br s, 1H), 8.08 (br d, J=11.2Hz, 1H), 7.99 (s, 1H), 7.53 (br s, 2H), 7.05 (s, 1H), 4.88-5.03 (m, 1H), 3.65-3.72 (m, 2H); 13C NMR (100 MHz, d6-DMSO) delta 146.1, 134.7, 128.9, 125.3, 118.4, 117.4, 66.3, 31.5; Mass spectrum (API-TIS) m/z 387/389 (M-H), 407/409 (MNH4+); Anal. calcd for C8H9BrClN3O4S2. EtOAc: C, 25.41; H, 2.50; N, 10.46; Found: C, 25.35; H, 2.44; N, 10.46.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1,1-dimethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; NitroMed, Inc.; US2006/189603; (2006); A1;,
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Application of 162705-07-9,Some common heterocyclic compound, 162705-07-9, name is (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)aniline, molecular formula is C18H21NO4, 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: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

The synthetic route of 162705-07-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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Synthetic Route 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.

General procedure: A 50 mL two-necked flask was replaced with argon followed by the addition of ligand 8 (10 mmol, 8a, 8b, 8c, 8d, 8e, 8f, 8g, or 8h), CuCl (30mmol, 3eq) and 25mL of dry dichloromethane (DCM). ), after replacing it three times with argon gas, the closed system was protected with an argon balloon. The ruthenium complex 4a (10 mmol) was added under argon atmosphere, and reacted at room temperature for 1.0 hour. Until the raw material 4a. After the reaction was completed, the silica gel was added to the filtrate, and the crude product was obtained by silica gel column chromatography, and then purified by washing with methanol or pentane-DCM to obtain a green solid product 9 (10 mmol, 9a, 9b, 9c, 9d, 9e, 9f, 9g, or 9h).

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; Zannan Science And Technology (Shanghai) Co., Ltd.; Zhan Zhengyun; (19 pag.)CN109134547; (2019); A;,
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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. 2393-23-9, name is 4-Methoxybenzylamine, A new synthetic method of this compound is introduced below., name: 4-Methoxybenzylamine

Pre aration of Intermediate 1-16.A mixture of p-anisaldehyde (1.8 mL, 14.8 mmol) and 4-methoxybenzylamine (1.9 mL, 14.8 mmol) in EtOH (50 mL) was refluxed for 4 h. On cooling to 0 C, NaBH4 (562 mg, 14.8 mmol) was added and the reaction mixture was stirred for 18 h at rt. On cooling to 0 C, water (50 mL) and DCM (250 mL) were added. The organic phase was separated and the aqueous layer was extracted with DCM (2 x 250 mL). The combined organic layers were dried (MgS04), filtered and evaporated. The residue was dissolved in Et20 (100 mL) and the mixture was cooled to 0 C. 4N HCI in dioxane (-10 mL) was added dropwise and the mixture was stirred for 2 h at 0 C. The resulting white solid was filtered off, washed with Et20/EtOAc to give the desired product (3.99 g, 91 %) as a white solid.1H NMR (300 MHz, DMSO) delta 9.40 (s, 2H), 7.45 (d, J = 8.7 Hz, 4H), 6.98 (d, J = 8.7 Hz, 4H), 4.03 (s, 4H), 3.77 (s, 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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; RODRIGUEZ HERGUETA, Antonio; RAMOS LIMA, Francisco, Javier; ALVAREZ ESCOBAR, Rosa, Maria; HIGUERAS HERNANDEZ, Ana Isabel; WO2011/141713; (2011); A1;,
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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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2,2-dimethoxypropane

Step B: To a suspension of 5-chloro-3-(trifluoromethyl)pyrazin-2-amine (0.77 g, 3.8 mmol) in iPrOH (6 ml) was added l-bromo-2,2-dimethoxypropane (0.57 ml, 4.2 mmol), pyridinium para-toluene sulfonic acid (0.1 g, 0.4 mmol) and the mixture heated to 100C in a sealed tube for 96h. The reaction was diluted with DCM, washed with saturated sodium hydrogen carbonate solution, dried (Na2S04) and concentrated. Purification by flash column chromatography on silica gel (EtOAc: Hept 3:7-1:0) afforded the titled product as a brown powder (0.15 g, 17%). MS (m/e): 236.1. (M+H+, CI)

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); A1;,
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Related Products of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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.

Step 2: (4-Bromo-2-methoxy-5-methylphenyl)(4-fluorophenyl)methanone4-Fluorobenzoyl chlo?de (1.40 mL, 11.9 mmol) was added dropwise to a suspension ofAlCl3 (1.73 g, 13.0 mmol) in 1 ,2-dichloroethane (30 mL) at room temperature. After 15 mm a solution of 3-bromo-4-methylanisole (2.17 g, 10.8 mmol) in 1 ,2-dichloroethane (3 mL) was added dropwise. The resulting mixture was stirred for 2 h, poured into 200 mL of ice-water, stirred for 20 min and extracted with CHCl3 (3x). The combined organics were washed with 5% aq. NaHCO3, brme, d?ed (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (EtOAc-hexane, 5:95) affording the title compound. 1H NMR (500 MHz, acetone-^): delta 7.86 (m, 2H), 7.38 (s, IH), 7.31-7.26 (m, 3H), 3.76 (s, 3H), 2.39 (s, 3H).

The synthetic route of 36942-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2006/99735; (2006); A1;,
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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. 109-85-3, name is 2-Methoxyethylamine, A new synthetic method of this compound is introduced below., SDS of cas: 109-85-3

Step 3: 4-Amino-N’-hydroxy-N-(2-methoxyethyl)-l,2,5-oxadiazole-3-carboximidamide [00186] 4-Amino-N-hydroxy-l ,2,5-oxadiazole-3-carboximidoyl chloride (200.0 g, 1.23 mol) was mixed with ethyl acetate (1.2 L). At 0-5 C 2-methoxyethylamine [Aldrich, product 143693] (119.0 mL, 1.35 mol) was added in one portion while stirring. The reaction temperature rose to 41 C. The reaction was cooled to 0 – 5 C. Triethylamine (258 mL, 1.84 mol) was added. After stirring 5 min, LCMS indicated reaction completion. The reaction solution was washed with water (500 mL) and brine (500 mL), dried over sodium sulfate, and concentrated to give the desired product (294 g, 1 19%) as a crude dark oil. LCMS for C6Hi2 503 (M+H)+: m/z = 202.3. 1H NMR (400 MHz, DMSO- ): delta 10.65 (s, 1 H), 6.27 (s, 2 H), 6.10 (t, J = 6.5 Hz, 1 H), 3.50 (m, 2 H), 3.35 (d, J = 5.8 Hz, 2 H), 3.08 (s, 3 H).

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; THE UNIVERSITY OF CHICAGO; GAJEWSKI, Thomas F.; SPRANGER, Stefani; LEUNG, Michael; WO2014/66834; (2014); A1;,
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Electric Literature of 41789-95-1, 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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of (+/-)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl) methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.; Example 2 Preparation of (+/-)-6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt Step A: To a mixture of (3-methoxybenzyl)methylamine (3.02 g, 20 mmol) and cesium carbonate (7.82 g, 24 mmol) in DMF (50 mL) was added cinnamyl bromide (4.47 g, 22 mmol). The reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with water and extracted with 1:1 hexanes/ethyl acetate (3×). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to provide the desired product (3.1 g, 58%): 1H NMR (CDCl3, 500 MHz) delta 7.39-7.37 (m, 2H), 7.32-7.29 (m, 2H), 7.23-7.20 (m, 2H), 6.93-6.91 (m, 2H), 6.81-6.78 (m, 1H), 6.54 (d, J=15.9 Hz, 1H), 6.31 (dt, J=15.9, 6.6 Hz, 1H), 3.81 (s, 3H), 3.52 (s, 2H), 3.19 (dd, J=6.6, 1.2 Hz, 2H), 2.25 (s, 3H); ESI MS m/z=268 [M+H]+. This crude product was used in the next step without further purification.

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-(3-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
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Electric Literature of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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 31; 2-ButyI-5-(3-chlorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-(3-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide (0.25Og, 0.75mmol) and 4-(difluoromethoxy)aniline (0.238g, 1.50mmol) were mixed in MeCN (2mL) and heated in a microwave reactor at 160C for 60 mins. The reaction mixture was evaporated and the residue was purified on a Horizon TM flash system using Heptane and EetOAc as eluant giving the title compound (0.25g, 72.9%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Difluoromethoxy)aniline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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Related Products of 36865-41-5, 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. 36865-41-5 name is 1-Bromo-3-methoxypropane, 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.

A mixture of l-bromo-3-methoxypropane (2.5 g, 16.34 mmol) and sodium sulfite (2.06 g, 16.34 mmol) in water (25 mL) was heated at reflux for 24 h. The solvent was evaporated and the formed solid was washed with a mixture of diethyl ether/toluene (8:2) and dried in vacuo. The solid was added in portions to phosphorus oxychloride (25 mL) and heated at 80 0C for 5 h and then at 100 0C for 2 h. The mixture was cooled to room temperature, diluted with dichloromethane and filtrated. The filtrate was concentrated, ethyl acetate was added followed by ice. The ice was allowed to melt and the organic phase was collected, washed with water and brine, dried over sodium sulfate and concentrated to give 2.8 g (100% yield) of the title compound: 3.35 (t, J= 6.53 Hz, 2 H), 3.20 (s, 3 H), 2.44 – 2.49 (m, 2 H), 1.74 – 1.81 (m, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-methoxypropane, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/58602; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem