Tag: M.W=100-200

2752-17-2, Adding a certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, 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 2752-17-2.

DIPEA (0.144 mL, 0.823 mmol) was added to a mixture of 6 (100.0 mg, 0.165 mmol) and 2,2′-oxydiethanamine (14.6 mg, 0.082 mmol) in DMF (0.82 mL) at rt. The mixture was cooled to 0 C before dropwise addition of T3P (0.145 mL, 50 wt % in EtOAc, 0.247 mmol), then let to gradually warm to rt. At 4 hr, volatiles were evaporated, and the reaction quenched with water and MeOH. The mixture was basified with NH4OH, filtered, and purified by reverse-phase HPLC (25-50% ACN in water, 5 mM NH4OH modifier) to afford 33% yield of white solid.

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

Reference:
Article; Ross, Audrey G.; Benton, Bret M.; Chin, Donovan; De Pascale, Gianfranco; Fuller, John; Leeds, Jennifer A.; Reck, Folkert; Richie, Daryl L.; Vo, Jason; LaMarche, Matthew J.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3468 – 3475;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1484-26-0, Name is 3-Benzyloxyaniline, 1484-26-0, 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.

Example 18; Preparation of Intermediate Compound 18C; Step A – Synthesis of Compound 18B; Compound 18A (commercially available) (10.0 g, 50.25 mmol) was dissolved in water at room temperature and to resulting suspension K2CO3 ( 3.8 g, 27.64 mmol) was added. 3- Chloro propionylchloride (7.0 g, 55.28 mmol) was added dropwise for 30 minutes and stirred ffoorr 22 hhoouurrss aatt RRTT.. TThhee pprreecciippiittaattee wwaass f fiilltteerreedd aanndd wwaasshheedc with water, 1 N HCl, dried at 500C under vacuum overnight to give 7.2 g of the product 18B.

Statistics shows that 3-Benzyloxyaniline is playing an increasingly important role. we look forward to future research findings about 1484-26-0.

Reference:
Patent; SCHERING CORPORATION; WO2009/32125; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, molecular formula is C10H12O2, 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. 2930-05-4

General procedure: In a 20 mL pressure tube (for volatile amines) was combined epoxide (1.0 mmol, 1.0 equiv) and amine (1.5 mmol, 1.5 equiv) 6.7 mL of reagent grade DMF. The reaction vessel fitted with a stirbar, sealed, and heated at 60C for 12 h after which the vessel was allowed to cool to ambient temperature (not necessary for reactions not ran in pressure vessels) before receiving deionized water (50 equiv) in one portion. The vessel was resealed and stirred at 60C for an additional 12 h. Solvent was removed on a rotary evaporator (22.5 mbar at 35C) and the crude residue loaded directly onto a silica gel column.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2930-05-4, its application will become more common.

Reference:
Article; Lizza, Joseph R.; Moura-Letts, Gustavo; Synthesis; vol. 49; 6; (2017); p. 1231 – 1242;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 658-89-9 as follows. 658-89-9

To a solution of 4-trifluoromethoxy-benzene-1, 2-diamine 2 (4.5 g, 23.4 itimol) and triethylamine (5.0 g, 49.5 iranol) in methylene chloride (100 ml) was added dropwise a solution of diphosgene (2.4 g, 12.1 mmol) in methylene chloride (10 ml) at 0-5C. The resulting suspension was stirred for 1 h at rt and filtered. The collected white solid was washed with water and dried to give 3.85 g (75%), mp 260-2620C.

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES, LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2006/50148; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

60792-79-2, Name is 2,2′-Oxybis(ethylamine) dihydrochloride, 60792-79-2, 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.

A suspension of 0.2 M 2,2′-oxydiethylamine dihydrochloride (0.247 gm, 1.35 mmole) and 0.4 M DIEA (0.47 ml, 2.7 mmole) in 4.5 DMF was added to 3-nitro-1,8-naphthalic anhydride (0.018 gm, 0.073 mmole) and heated at 150 C with microwave treatment under nitrogen for 5 minutes. The mixture was cooled, treated with 25 ml 1.3 M aqueous TFA, and concentrated to about 2 ml. The residue was diluted with dichloromethane, washed with sat. NaCl, dried over MgSO4, and concentrated under vacuum to give N- aminoethylethoxy-3-nitro-1,8 naphthalimide 7. MS m/z 330 (M + H)+.

Statistics shows that 2,2′-Oxybis(ethylamine) dihydrochloride is playing an increasingly important role. we look forward to future research findings about 60792-79-2.

Reference:
Patent; GENENTECH, INC.; WO2006/60533; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

366-99-4, name is 3-Fluoro-4-methoxyaniline, 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. 366-99-4

To a stirred suspension of 3-fluoro-p-anisidine (3.00 g, 21 mmol) in CH2Cl2 (10 mL) is added acetic anhydride (2.0 mL, 21 mmol) over 1 h while maintaining the temperature between 25-30¡ã C. using a cold water bath. The solution is then stirred for 2 h at 25¡ã C. Additional 1 mL of acetic anhydride is added to the solution, which is then stirred for an additional 2 h. Hexane (30 mL) is slowly added to the mixture over 1 h. The product is collected by filtration, concentrated in vacuo and dried in oven to give 3.40 g (90percent yield) of N-(3-fluoro-4-methoxyphenyl)acetamide as tan crystals. 1H NMR (400 MHz, CDCl3) delta 7.41, 7.19, 7.11, 6.90, 3.87, 2.16. In a 100 mL, three-necked flask equipped with a thermometer and a dropping funnel chilled in an ice-salt bath, N-(3-fluoro-4-methoxyphenyl)acetamide (3.0 g, 16 mmol) is dissolved in 98percent sulfuric acid, care being taken that the temperature does not rise above 5¡ã C. To this solution 2.6 mL of nitric acid is added dropwise at such a rate that the temperature does not rise above 5¡ã C. After all the nitric acid is added, the viscous orange mass is poured onto 50 g of cracked ice and the mixture is thoroughly stirred. The yellow crystals that separate are filtered off and thoroughly washed with water to yield 3.33 g (89percent yield) of N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide as yellow crystals. 1H NMR (400 MHz, DMSO-d6) delta 10.60, 10.17, 7.75, 7.73, 7.62, 7.59, 4.03, 3.92, 2.06. A suspension of N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide (3.0 g, 13 mmol) in 38 mL of water, 38 mL of HCl and 15 mL of ethanol is refluxed for 30 minutes. On cooling, crystals that separate are recrystallized from ethanol to yield 0.71 g (29percent yield) of 5-fluoro-4-methoxy-2-nitroaniline as red crystals. 1H NMR (400 MHz, CDCl3) delta 7.68, 6.56, 6.04, 3.87. Example 603 is obtained according to Method F, making non-critical modifications. Yield 60percent. HRMS (ESI) calcd for C12H11FN4O5+H 311.0792 found 311.0798.

Statistics shows that 366-99-4 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-4-methoxyaniline.

Reference:
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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: Diester1 (1mmol) and the appropriate diamine2-6 (1mmol) were dissolved in dry methanol (50mL) and sodium methoxide (2mmol) was added. A mixture was stirring for 72hat room temperature. After completion of the reaction (controlled by TLC), the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography (1-5% MeOH in CH2Cl2). All the macrocyclic products obtained in this way are colourless solids, stable to air. 4.2.1 Macrocycle (R)-714b (0010) Yield: 60% (282mg); [alpha]D25 +86.4 (c=0.1, CH2Cl2); Mp. 245-246C; 1H NMR (400MHz, CDCl3):delta=8.02 (d, J=9.0Hz, 2H), 7.90 (d, J=8.2Hz, 2H), 7.45-7.21 (m, 6H), 7.07 (d, J=8.5Hz, 2H), 6.41 (br s, 2H), 4.60 (d, J=15.6Hz, 2H), 4.36 (d, J=15.6Hz, 2H), 3.71-3.56 (m, 2H), 3.51-3.39 (m, 2H), 3.38-3.27 (m, 2H), 2.97-2.86 (m, 2H); 13C NMR (100MHz, CDCl3):delta=168.5, 152.7, 133.6, 130.2, 129.8, 128.1, 127.2, 125.0, 124.6, 119.6, 114.1, 68.9, 68.7, 38.5; IR (film) 3423, 3294, 3056, 2914, 2866, 1674, 1533, 1507, 1273, 1213, 1094, 808, 735cm-1.

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 2752-17-2.

Reference:
Article; Pikus, Grzegorz; Jurczak, Janusz; Tetrahedron; vol. 72; 16; (2016); p. 1928 – 1932;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 321-28-8

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.

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

Reference:
Patent; G.D. Searle & Co.; US5990148; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

A mixture of a-7 (0.001 mol), meta- (OCF3)-aniline (0.0015 mol), supported cyano-borohydride (0.0021 mol) and acetic acid (6 drops) in methanol was stirred at room temperature for 48 hours, and then filtered. The filtrate was evaporated. The residue was taken up in CH2Cl2/methanol. The organic layer was washed with a solution of K2C03 10percent, dried over magnesium sulfate, filtered and the solvent was evaporated. The residue (0.42g) was purified by column chromatography over silica gel (eluent: CH2Ck/CH30H/NH4OH 93/7/0. 5 ; 15-35 pm). The pure fractions were collected and the solvent was evaporated. The residue (0. 15g, 32percent) was crystallized from CH3CN/methanol. The precipitate was filtered off and dried, yielding 0.085g (18percent, compound 4, melting point: 156¡ãC) of 2-{2-Amino-6-[(3-trifluoromethoxy- phenylamino)-methyl]-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58869; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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: A mixture of aldehyde (1.97 mmol), amine (1.97 mmol), acetylene (2.95 mmol), and thecorresponding supported Au catalyst (1% wt, 60 mg, 0.002 mmol) was heated at 60 C for 8 h,after which time the solution was cooled and the catalyst was removed by filtration. The filtrate wasevaporated under reduced pressure to afford propargylamine 5. Yields were determined by integration of the 1H-NMR spectra of the crude reaction mixtures. After separation and washing with n-pentane,the catalyst was reused intact for the next reaction without any further pre-treatment.

According to the analysis of related databases, 2′-Methoxyphenyl acetylene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Soengas, Raquel; Navarro, Yolanda; Iglesias, Maria Jose; Lopez-Ortiz, Fernando; Molecules; vol. 23; 11; (2018);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem