Month: May 2021

These common heterocyclic compound, 35472-56-1, name is Ethyl 2-(methylamino)benzoate, 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. Quality Control of Ethyl 2-(methylamino)benzoate

EXAMPLE 26 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-1-methyl-quinazoline-2,4(1H,3H)-dione hydrochloride N-Methyl-2-carboethoxyaniline (5.0 g, 28 mmol) was treated with 2-chloroethylisocyanate (2.86 mL, 28 mmol) at reflux in toluene for 18 hours. The reaction was cooled to 25 C., and the crystalline product was collected by filtration to yield the intermediate 1-methyl-3-(2-chloroethyl)-quinazoline-2-4-dione.

The synthetic route of Ethyl 2-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US5521181; (1996); A;,
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Synthetic Route of 139911-28-7, 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. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(O) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of ethyl 2-bromo-5-fluorobenzoate (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mLeach of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate an the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta7.7 (dd, 1H), 7.5 (m, 1H), 7.25-6.75 (m, 4H), 4.0 (q, 2H), 2.0 (s, 3H), 1.0 (t, 3H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

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, Ethyl 2-bromo-5-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US4864028; (1989); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 66315-23-9,Some common heterocyclic compound, 66315-23-9, name is Ethyl 3-amino-4-(methylamino)benzoate, molecular formula is C10H14N2O2, 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 2-1-1 Ethyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate Ethyl 3-amino-4-methylaminobenzoate (1.00 g, 5.15 mmol) prepared in the Step 1-1-3 was dissolved in acetic anhydride (4 ml), and the mixture was heated under reflux for 19 hours. After being allowed to cool, the mixture was neutralized with a saturated sodium bicarbonate solution and subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.15 g, quantitative) as a light-brown oily substance. 1H-NMR (CDCl3) delta: 8.39 (d, J=1.5 Hz, 1H), 7.98 (dd, J=1.5, 8.5 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.39 (q, J=6.9 Hz, 2H), 3.75 (s, 3H), 2.62 (s, 3H), 1.41 (t, J=6.9 Hz, 3H) Mass, m/z: 218 (M+), 173 (base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-amino-4-(methylamino)benzoate, its application will become more common.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 37555-99-0, These common heterocyclic compound, 37555-99-0, name is Diethyl 2-ethoxymalonate, 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.

Part A Preparation of mono-ethyl ethoxymalonate Diethyl ethoxymalonate (10.08 grams, 0.05 mole), prepared as described in Example LXVII, Part B, was saponified with potassium hydroxide (2.77 grams, 0.05 mole) in a mixture of 200 milliliters of ethanol and 0.88 gram (0.05 mole) of water and worked up under conditions similar to those described in Example LIX giving 4.32 grams (0.02 mole) of mono-ethyl ethoxymalonate as a residue product. NMR analysis of the product indicated the following: ‘H NMR(CDCl3) delta1.13-1.49(2xt, 6H, 2*CH3), 3.51-3.95(q, 2H, ether CH2 O), 4.10-4.50(q, 2H, ester CH2 O), 4.53(s, methine CH), 6.95(s, COOH) ppm.

The synthetic route of 37555-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Nederland B.V.; US5123951; (1992); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 871224-19-0, 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. 871224-19-0, name is Methyl 3-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of methyl 3-bromo-2-chlorobenzoate (2.3 g, 9.27 mmol) in 1,4-dioxane (20 mL) at room temperature were added (Bpin)2 (3.5 g, 13.91 mmol), KOAc (2.7 g, 27.8 mmol) and Pd2(dppf).CH2Cl2 (0.34 g, 0.46 mmol) and degassed with argon for 5 min. The resulting mixture was maintained at 100 C. for 16 h. The reaction mixture was filtered through celite pad and the filtrate was concentrated under reduced pressure to get methyl 2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (5 g crude compound) as a dark brown semi-solid. The crude product was used for the next step without 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, Methyl 3-bromo-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Polaris Pharmaceuticals, Inc.; WEBBER, Stephen E.; ALMASSY, Robert J.; (75 pag.)US2018/65917; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl cyclopropanecarboxylate

Example 21A tert-Butyl 1-(3-bromo-4-chlorobenzyl)cyclopropanecarboxylate [0434] THF and cooled to -30 C. 400 ml (1.0 mol) of n-butyllithium solution (2.5 M in hexane) were added dropwise. The resulting mixture was warmed to 0 C. and then cooled to -70 C. A solution of 94.8 g (0.667 mol) of tert-butyl cyclopropanecarboxylate in 750 ml THF was added to the reaction solution, with the temperature being kept below -60 C. After 4 h of stirring at -60 C., a solution of 208.6 g (0.733 mol) of 2-bromo-4-(bromomethyl)-1-chlorobenzene in 550 ml of THF was added, the temperature again being kept below -60 C. The reaction mixture was slowly warmed to RT overnight, and saturated aqueous ammonium chloride solution was then added carefully. After phase separation, the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ dichloromethane 4:1). This gave 95.5 g (41.4% of theory) of the title compound. [0436] GC-MS (Method 1): Rt=6.54 min; m/z=288/290 (M-C4H8)+. [0437] LC-MS (Method 3): Rt=1.65 min; m/z=288/290 (M-C4H8)+.

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; Lampe, Thomas; Hahn, Michael; Stasch, Johannes-Peter; Schlemmer, Karl-Heinz; Wunder, Frank; El Sheikh, Sherif; Li, Volkhart Min-Jian; Becker-Pelster, Eva Maria; Stoll, Friederike; Knorr, Andreas; US2015/152050; (2015); A1;,
Ester – Wikipedia,
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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. 20610-77-9, name is 4-Aminophenyl 4-aminobenzoate, A new synthetic method of this compound is introduced below., name: 4-Aminophenyl 4-aminobenzoate

4.56 g of 4-aminophenyl 4-aminobenzoate (20.0 mM) were suspended in 140 ml of water and 25 ml of hydrochloric acid 37 %. The suspension was cooled to 3 C and a solution of 2.83 g of sodium nitrite (41.0 mM) in 10 ml of water was added dropwise. When the addition was complete, the mixture was stirred for 1 h at 3C, then the excess of nitrite was destroyed by addition of ca. 0.5 g of amidosulfonic acid and the mixture was stirred for further 10 min. This diazo-solution was added to a solution of 5.73 g of 1-naphthylamine (40.0 mM) in 40 ml of ethanol at 5-10C. When addition was complete, the coupling mixture was stirred for 1 h at 3 C, then 37.0 g of potassium acetate were added and stirring was continued for 0.5 h. The pH of this mixture was then adjusted to pH = 7 by addition of ammonia solution 26 %. The mixture was poured onto 800 ml of ice-water and the dark precipitate was filtered off, washed with water and dried to give 17.60 g of dark crystals. These crystals were boiled for 1 h in 150 ml of methanol, the formed suspension was cooled to room temperature and the solid was filtered off, washed with methanol and dried to give 6.60 g (12.3 mM, 61 %) of 4-[(E)-(4-amino-1-naphthyl)diazenyl]phenyl 4-[(E)-(4-amino-1-naphthy)diazenyl]benzoate as dark crystals.

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; Rolic AG; EP1593713; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3070-71-1, name is Methyl 2-benzylacrylate, belongs to esters-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 3070-71-1, Quality Control of Methyl 2-benzylacrylate

(1) Compound (7) (239.7 mg, 0.93 mmol) obtained in Example 7 was dissolved in dehydrated toluene (5.0 mL), Compound (4) (R2=Bn, R=Me) (530 mg, 3.0 mmol) synthesized according to a method of Basavaiah et al. (Tetrahedron Lett. Vol. 42, 477-479 (2001)) was added to the solution, and the mixture was stirred for 12 hr at 60 C. under nitrogen atmosphere and further for 2 hr at 90 C. The reaction mixture was concentrated in vacuo, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain a crude body of Compound (8) (R1=Ph(CH2)2, R2=Bn, R=Me).

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, Methyl 2-benzylacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2005/182032; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 64321-95-5, name is Methyl 2-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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. Quality Control of Methyl 2-amino-3-(trifluoromethyl)benzoate

To a stirred solution of No.105 methyl 2-amino-3-(trifluoromethyl)benzoate (IV-34, 3.6 g, 16.4 mmol) in No.107 CH3CN (22 mL) was added No.108 HBr (48% (aq), 20.3 mL) dropwise at 0C. over 10 min. Then, No.71 NaNO2 (1.25 g, 18.1 mmol) in No.21 water (5 mL) was added dropwise over 1 h at 0C. with vigorous stirring. After addition, the solution was stirred for 5 min at 0C. followed by the addition of No.109 CuBr (2.71 g, 18.9 mmol) in portions over 30 min. The mixture was heated at 70C. for 1 h then cooled again to 0C. before being diluted with water (40 mL) and extraction with EtOAc (350 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4), concentrated to dryness under reduced pressure, and chromatographed (ethyl acetate/hexanes, 1:9) to afford a clear No.96 oil (3.47 g, 75%). 1H NMR (500 MHz, CDCl3) delta 7.74 (dd, J=8.0, 1.7 Hz, 1H), 7.69 (dd, J=7.7, 1.7 Hz, 1H), 7.43 (t, J=7.8 Hz, 1H), 3.92 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 166.77, 136.82, 133.04, 131.53 (q, J=31.0 Hz), 129.78 (q, J=5.6 Hz), 127.38, 122.77 (q, J=273.8 Hz), 118.56, 52.93. 19F NMR (376 MHz, CDCl3) delta -62.78 (s, 3F). HRMS [M+H]+ Calcd for C9H6BrF3O2 282.9576; found 282.9575.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64321-95-5, its application will become more common.

Reference:
Patent; Northwestern University; Silverman, Richard B.; Le, Hoang V.; McLeod, Rima L.; Hawker, Dustin D.; (53 pag.)US2018/98952; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 76008-73-6, 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. 76008-73-6, name is Ethyl 5-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) (+/-)-2-Chloro-5-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-benzoic acid, ethyl ester Prepared as described in Example 5a) using 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), 3-pyrrolidinyl-carbamic acid 1,1-dimethylethyl ester (0.42 g), cesium carbonate (0.86 g), palladium (II) acetate (21 mg) and (R)-BINAP (88 mg) and toluene (3 ml) to afford the subtitle compound as an oil (0.25 g). MS (APCI+ve) 311/313 (M-BOC)+

The synthetic route of Ethyl 5-bromo-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6492355; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics