Month: March 2021

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. 105-53-3, name is Diethyl malonate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Diethyl malonate

[Reference Example 3] Production of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane 8.79 g (54.9 mmol) of diethyl malonate and 99 mL of toluene were added into a three-necked flask (300 mL), and thereafter, 20.5 mL (52.4 mmol) of a 20% sodium ethoxide ethanol solution was added thereto as a base. The obtained mixture was stirred at room temperature for 0.5 hours. Thereafter, 9.89 g (24.9 mmol) of cis-1,4-di-4-toluenesulfonyloxy-2-butene, which had been obtained by performing the same operations as those in Example 1 and then purifying the obtained compound by silica gel chromatography, was added to the reaction solution. The obtained mixture was stirred at room temperature for 3.5 hours, and thereafter, 59.9 mL of a 1 M sodium hydroxide aqueous solution was added to the reaction solution. The obtained mixture was stirred for 1 hour, and an organic layer was then separated. A water layer was re-extracted with 50 mL of toluene, and organic layers were gathered. The gathered organic layer was washed with 50 mL of water three times, and the resultant was then filtrated, while washing the residue with toluene. The obtained filtrate was concentrated at 45C under reduced pressure, so as to obtain 22.4 g of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane in the form of a crude product of a light yellow oily substance. This crude product contained 1.25 g of 1,1-di-ethoxycarbonyl-2-vinylcyclopropane (yield: 24%) and 3.94 g of 1,1-di-ethoxycarbonyl-3-vinylcyclopentene (yield: 74%).

According to the analysis of related databases, 105-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; API Corporation; EP2537825; (2012); 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. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl 4-(aminomethyl)benzoate

To a stirred solution of 5-chloro-2-hydroxybenzoic acid (0.57 g, 3.3 mmol) and tert-butyl 4-(aminomethyl)benzoate (0.72 g, 3.5 mmol) in dichloromethane (5 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCl) (0.95 g, 5.0 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (0.76 g, 5.0 mmol), and triethylamine (0.46 mL, 3.3 mmol). After being stirred overnight, the reaction mixture was poured into sodium bicarbonate aqueous solution (50 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (20 mL*2). The combined organic layers were washed with brine (50 mL), dried (magnesium sulfate), and evaporated. The residue was purified by flush column chromatography on silica gel eluding with hexane/ethyl acetate (10/1) to afford 0.57 g (48%) of the title compound as white solids: 1H-NMR (CDCl3) delta 12.12 (1H, s), 7.99 (2H, d, J=7.9 Hz), 7.47-7.30 (4H, m), 6.97 (1H, d, J=8.4 Hz), 6.67-6.52 (1H, m), 4.68 (2H, d, J=5.7 Hz), 1.59 (9H, s).

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; Pfizer Inc; US2005/250818; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 39503-58-7, 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. 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

The bromo derivative from above (44.5 g, 0.17 mol) was added in small portions to conc. H2SO4 (170 mL) and the mixture was stirred in an ice-salt bath until all SOLIDS DISSOLVED. CONC. HN03 (17 mL) was then added dropwise over 20 min and stirring continued for an additional hour in the ice bath. The reaction mixture was then slowly added to ice-water (2 L) and the precipitated yellow solid was collected by filtration. The solid was washed with water, NAHC03 solution and water again. After drying, the desired nitro derivative was obtained as an orange solid (36.8 g).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-bromo-2-methoxy-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/65367; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 106-32-1,Some common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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.

Ethyl octanoate (105 g, 0.61 mol) was dissolved in methanol (420 mL, 4 V) and stirred, then pumped into the coil with pump A at a rate of 5.6 g/min, sodium borohydride (33.86 g, 0.92 mol), EtONa (1.24g, 0.018mol) was dissolved in methanol (105mL, 1V) and pumped to a 240mL coil with pump B at a rate of 1.5g / min. The coil was immersed in a 40 C oil bath, and the outlet was sampled by HPLC. The system was subjected to quenching extraction in a 2 L four-necked flask and subjected to column chromatography to obtain 70 g of a product in a yield of 80%.

The synthetic route of 106-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kailaiying Pharmaceutical Group (Tianjin) Co., Ltd.; Hong Hao; Lu Jiangping; Zhang Enxuan; Liu Zhiqing; Zhang Tao; (21 pag.)CN110156549; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 15568-85-1, These common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

4-Methoxyaniline (1.27 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.82 g) were dissolved in 2-propanol (40 ml), and the solution was stirred at 50C for 2 hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give 5-[(4-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dio xan-4,6-dione (1.98 g, yield 73%). 5-[(4-Methoxy-phenylamino)-methylene]-2,2-dimet hyl-[1,3]dioxan-4,6-dione (1.28 g) and biphenyl (5.2 g) were suspended in diphenyl ether (20 ml), and the suspension was stirred at 220C for one hr. The reaction mixture as such was purified by column chromatography with a methanol-chloroform system to give 6-methoxy-1H-quinolin-4-one (398 mg, yield 49%). 6-Methoxy-1H-quinolin-4-one (398 mg) was suspended in diisopropylethylamine (3 ml), phosphorus oxychloride (1 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling, and the aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution. The organic layer was extracted with ethyl acetate, and the ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 4-chloro-6-methoxyquinoline (375 mg, yield 42%).

The synthetic route of 15568-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); 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. 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2-amino-5-methylbenzoate

a) 5-Methyl-2-methylaminobenzyl chloride hydrochloride Ethyl 2-amino-5-methylbenzoate was treated with dimethylsulfuric acid to give a N-methylated product. The N-methylated product was reduced using lithium aluminum hydride to give 5-methyl-2-methylaminobenzyl alcohol.

The synthetic route of 58677-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; US5082943; (1992); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 457097-93-7, These common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)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.

(b) 4-Amino-3-chloro-5-trifluoromethoxy-benzoic acidmethyl ester The product of the previous step (200.0 mg, 0.74 mmol) was dissolved in a mixture of ACN (9.44 mL) and DMA (0.944 mL) at RT. To this stirred solution was added N-chlorosuccinimide (108.2 mg, 0.81 mmol). The resulting mixture was heated at 60 C. for 1 h, cooled to RT and partitioned between EtOAc (20 mL) and saturated sodium bicarbonate (4 mL). The organic layer was washed with saturated sodium bicarbonate (4 mL) and brine (4 mL), dried over sodium sulfate, filtered, and concentrated to give a yellowish oil, which was purified by silica gel chromatography (12 g silica gel, 0-40% EtOAc/hexanes) to give the title intermediate as a white solid (173.8 mg, 88% yield). Structure confirmed by NMR.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

Into an 100-mL 3 -necked round-bottom flask was added a solution of 1 ,4- dibromobenzene (0.23 g, 0.99 mmol) in tetrahydrofuran (50 mL). The solution was placed under nitrogen and cooled to -78C. w-Butyllithium (0.4 mL,2.5 M) was added dropwise, and the resulting solution was stirred for 30 min at the same temperature. Ethyl 2,2-difluoroacetate(0.14 g, 1.1 mmol) was added dropwise to the mixture and the resulting solution was stirred for an additional 1 h at -78C. The reaction was quenched by the careful addition of hydrochloric acid (2.0 mL, 1.0 M). The mixture was extracted with ethyl acetate (2 x 10 mL), and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford l-(4-bromophenyl) 2,2-difluoroethan-l-one. GCMS calc’d for C8H5BrF20[M]+: 234, found 234.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 50893-36-2, These common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, 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 10 To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-tetrazol-1-yl)phenyl]-2-imidazolidinone (0.61 g) and 1-chloroethyl ethyl carbonate (3.7 g) was added acetonitrile (1 ml), and the mixture was stirred for 38 hours at 95¡ã C. The reaction mixture was concentrated under reduced pressure. To the residue was added diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The elude was concentrated in vacuo. The residue was dissolved in water (10 ml), and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride (Compound 7,90 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 1.21,1.22(3H,t,J=7 Hz), 1.79,1.80(3H, d,J=6 Hz), 3.62~4.23(6H,m), 4.65~5.10(3H,m), 6.69~6.82(2H,m), 6.94~7.04(1H,m), 7.26~7.38(2H,m), 7.90(4H,s), 9.23(0.5H,s), 9.27(0.5H,s), 10.08(1H,s), 10.72(0.5H,s), 10.82(0.5H,s).

The synthetic route of 50893-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6407129; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, 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 57381-62-1, name: Methyl 2-bromo-4-chlorobenzoate

In a 500 ml round-bottomed flask, 30 g (68.9 mmol) of the compound of formula C-1,17 g (68.2 mmol) of methyl 2-bromo-4-chlorobenzoate,1.6 g (1.38 mmol) of tetrakistriphenylphosphine palladium was added to 150 ml of tetrahydrofuran, mixed with 80 ml of an aqueous solution of 28.6 g (207 mmol) of potassium carbonate and refluxed for 24 hours. The impurities were removed using chloroform and water, and then anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized using chloroform and ethanol to obtain 21.2 g (yield 65percent) of the formula C-2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; LG Chemical Co.,Ltd; Kim, Su Yeon; Lee, Ho Yong; Jo, Sung Mi; (43 pag.)KR2016/2354; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics