Month: June 2021

Reference of 91085-56-2, 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. 91085-56-2 name is Ethyl 3,5-dichlorobenzoate, 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.

General procedure: Ethylbenzoates (11-15, 1.5g, 9.98 mmol)and ethyl-2-phenylacetates (16-20, 1.5g, 9.13 mmol)were dissolved in ethanol and then hydrazine-hydrate(99%) was added and reux for 8-12h. Ethanol wasconcentrated and the resultant residue was pouredin ice cold water and stirred for 15 -20 min, the solidsthat were thrown out was fltered at the pump anddried to obtain the corresponding benzohydrazides(21-25) and 2-phenylacetohydrazides (26-30) in 80-82% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,5-dichlorobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Kumar Reddy; Kathale, Niren E.; Oriental Journal of Chemistry; vol. 33; 2; (2017); p. 971 – 978;,
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Related Products of 25109-86-8, A common heterocyclic compound, 25109-86-8, name is Methyl 2-(2-bromoethyl)benzoate, molecular formula is C10H11BrO2, 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.

Methyl 2-(2-(4-Chloro-2-nitrophenoxy)ethyl)benzoate To a solution of 4-chloro-2-nitrophenol (985 mg, 5.68 mmol) in DMF (10 ml) was added crude Intermediate 33 (1.38 g, 5.68 mmol) and K2CO3 (3.9 g, 28.4 mmol) and the reaction was stirred at 90 C. for 16 hours, diluted with H2O, and the resulting solution was extracted with EtOAc and washed with brine, dried over Na2SO4 and concentrated in vacuo, followed by MPLC purification to yield Intermediate 34 (520 mg, 27% for 2 steps). 1H NMR (600 MHz, CDCl3) delta 7.96 (dd, J=1.17, 7.92 Hz, 1H), 7.79 (d, J=2.64 Hz, 1H), 7.47-7.53 (m, 1H), 7.41-7.46 (m, 2H), 7.33 (td, J=1.17, 7.63 Hz, 1H), 7.07 (d, J=8.80 Hz, 1H), 4.39 (t, J=6.31 Hz, 2H), 3.91 (s, 3H), 3.49 (t, J=6.31 Hz, 2H).

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; ALLERGAN, INC.; YUAN, HAIQING; BEARD, RICHARD L.; LIU, XIAOXIA; DONELLO, JOHN E.; VISWANATH, VEENA; GARST, MICHAEL E.; US2013/231338; (2013); A1;,
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Related Products of 140-39-6, The chemical industry reduces the impact on the environment during synthesis 140-39-6, name is p-Tolyl Acetate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of aryl ester (25 mmol), HFSiO2 (2 g), and EtOAc (5 mL) was charged in a 50 ml flask and stirred for 5min. EtOAc was used for homogenization of the reactionmixture in this step. The solvent was evaporated under vacuumand the residue was heated with the classical method for 4 h at 55C for aryl acetates and at 75C for aryl benzoates(Table 1). After cooling, the reaction mixture was extractedwith EtOAc (3 × 10 mL) and the solvent was removed under vacuum. The residue was subjected to short column chromatography (EtOAc/hexane; 1:5) on silica gel to obtain pureproducts. All the isolated hydroxyaryl ketones successfullygave the related spectral data of IR, 1H NMR, 13C NMR andMS spectrometers (see the Supporting Information, Fig. 12S-39S) and comparison with authentic samples prepared byreported methods [33-36].

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, p-Tolyl Acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Paghandeh, Hossein; Saeidian, Hamid; Ghaffarzadeh, Mohammad; Letters in Organic Chemistry; vol. 15; 9; (2018); p. 809 – 814;,
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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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, A new synthetic method of this compound is introduced below., Computed Properties of C13H27NO5

To the solution of intermediate 20 (22 mg, 0.03 mmol) in DMSO (3.0 mL) were added NMM (10 mg, 0.09 mmol), tert-butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate (13 mg, 0.04 mmol), HOAt (6.4 mg, 0.05 mmol), and EDCI (46 mg, 0.05 mmol). The mixture was allowed to stir at room temperature overnight. The progress of the reaction was monitored by LC-MS. Upon completion, the mixture was concentrated under vacuum and purified by preparative HPLC to afford intermediate 21 (21 mg, 70%). The solution of intermediate 21 (21 mg, 0.02 mmol) in formic acid (5.0 mL) was stirred overnight at room temperature. The progress of the reaction was monitored by LC-MS. Upon completion, the reaction was concentrated under vacuum and the resulting residue was dissolved in DMSO (2.0 mL). To the resulting solution were added VHL-1 (13 mg, 0.03 mmol), NMM (14 mg, 0.14 mmol), HOAt (4.6 mg, 0.03 mmol), and EDCI (6.5 mg, 0.03 mmol). The reaction mixture was allowed to stir at room temperature overnight. The progress of the reaction was monitored by LC-MS. Upon completion, the mixture was concentrated under vacuum and purified by preparative HPLC to afford XY019-083 (4.5 mg, 16%) as solid. 1H NMR (600 MHz, CD3OD) delta 8.90 (s, 1H), 8.32 (s, 1H), 7.74 (s, 1H), 7.68 (s, 1H), 7.45 (d, J = 8.1 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 6.32 (d, J= 21.1 Hz, 1H), 6.13 (s, 1H), 5.06 – 4.99 (m, 1H), 4.64 (d, J = 8.9 Hz, 1H), 4.58 – 4.45 (m, 5H), 4.40 – 4.30 (m, 2H), 4.24 (s, 1H), 4.00 – 3.94 (m, 2H), 3.90 – 3.83 (m, 2H), 3.82 – 3.36 (m, 25H), 2.93 – 2.85 (m, 2H), 2.71 (d, J = 45.0 Hz, 2H), 2.59 -2.50 (m, 1H), 2.46 (s, 3H), 2.41 (s, 3H), 2.26 – 2.17 (m, 4H), 2.07 (d, J = 8.8 Hz, 1H), 1.54 (d, J = 6.5 Hz, 6H), 1.02 (s, 9H). MS (m/z) [M + H]+: 1240.2.

The synthetic route of 252881-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; JIN, Jian; PARSONS, Ramon; STRATIKOPOULOS, Ilias; YANG, Xiaobao; (168 pag.)WO2018/81530; (2018); A1;,
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Reference of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

NaHMDS (2M, 5.50 mL) was added to a solution of pent-4-enenitrile (0.97 mL, 10.0 mmol) in anhydrous THF (50 mL) at -78 oC. After stirring for 15 min, methyl-3-chlorobenzoate (1.88 g) was added and the reaction was stirred for 30 min befor warming to room temperature. The reaction was quenched by addition of 1N HCl solution, then extracted with EtOAc (x 2). The combined organics were dried and concentrated to give the acylated nitrile (2.18 g, 99%). Hydroxylamine hydrochloride (382 mg) was added to a solution of the acylated nitrile (1.1 g) in pyridine (10 mL) and the reaction was stirred at 80 oC for 3 hours. After cooling to room temperature, EtOAc and sat. NH4Cl solution were added and the layers separated. The organic was washed with brine, dried over Na2SO4 and concentrated to give the amino-isoxazole as a yellow oil (1.05 g, 89%) which was used directly. The residue was dissolved in pyridine (5 mL) and cooled in an ice-bath. AcCl (0.36 g, 4.5 mmol) was added and the reaction was stirred for 30 min before warming to room temperature for a further 30 min. The volatiles were removed under vacuum and the residue was purified by silica gel chromatography [heptane/EtOAc, 9:1 – 3:1] to give the product as a colourless oil (0.96 g, 77%). The N-acyl intermediate (950 mg, 3.43 mmol) was then N-alkylated with allyl bromide and NaH to give the product 19 as a colourless oil (855 mg, 79%)

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-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Moss, Thomas A.; Tetrahedron Letters; vol. 54; 8; (2013); p. 993 – 997;,
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Reference of 40876-98-0, The chemical industry reduces the impact on the environment during synthesis 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 1a (109 mg, 0.5 mmol) and 2a (116 mg, 0.55 mmol) in DMF (1.0 mL) was stirred at 120 C for 1 h. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/EtOAc, 4:1), compound 4a was obtained as pale yellow oil, 123 mg (75%). Other compounds were synthesized similarly, and the spectroscopic data of 4a fare as follows.

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, Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Jin; Kim, Ko Hoon; Lee, Hyun Ju; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 34; 10; (2013); p. 3027 – 3032;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 34529-06-1, name is Dimethyl 3-aminophthalate, molecular formula is C10H11NO4, 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. Application In Synthesis of Dimethyl 3-aminophthalate

3-(2-Methoxy-ethylamino)-phthalic acid dimethyl ester To a stirred solution of oxalyl chloride (1.75 ml, 20 mmol) in methylene chloride (20 ml) under a nitrogen atmosphere at -78 C. was added DMSO (1.42 ml, 20 mmol) in methylene chloride (10ml) dropwise over 5 minutes. The mixture was stirred for 5 minutes followed by the dropwise addition of 2-methoxyethanol (1.58 ml, 20 mmol) in methylene chloride (10 ml) over 5 minutes. The mixture was stirred for 20 minutes followed by the dropwise addition of triethylamine (8.36 ml, 60 mmol) over 5 minutes. The resulting suspension was stirred for 30 minutes at -78 C. and then allowed to warm to room temperature. The reaction mixture was diluted with methylene chloride (20 ml). To this stirred mixture was added 3-amino-phthalic acid dimethyl ester (2.09 g, 10 mmol) and acetic acid (4.60 ml, 80 mmol). The mixture was stirred at room temperature under a nitrogen atmosphere for 5 minutes followed by the addition of sodium triacetoxyborohydride (4.24 g, 20 mmol). The mixture was stirred for 3 h. The reaction mixture was diluted with methylene chloride (50 ml) and washed with water (3*100 ml), saturated aqueous sodium bicarbonate (2*100 ml), brine (100 ml), and dried (MgSO4). The solvent was evaporated in vacuo and the residue purified by chromatography (25% ethyl acetate/hexane) to give 2.24 g (84%) of product as an oil. 1H NMR (DMSO-d6) d 7.32 (t, J=8.0 Hz, 1H), 6.88-6.79 (m, 3H), 3.85 (s, 3H), 3.83 (s, 3H), 3.62 (t, J=5.4 Hz, 2H), 3.41 (s, 3H), 3.35 (q, J=5.2 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 34529-06-1, its application will become more common.

Reference:
Patent; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 4630-80-2, 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 4630-80-2 as follows.

To a suspension of NaH (2.75 g, 68.7 mmol) in THF (15 ml_) at 700C was added dropwise a solution of methyl cyclopentanecarboxylate (8.00 g, 62.4 mmol) and anhydrous acetonitrile (3.91 ml_, 74.9 mmol) in THF (5 ml_). The mixture was stirred for 16 h at 70C-72C, cooled to rt, and diluted with ethyl acetate and aqueous HCI. The organic layer was washed successively with water and brine and dried (MgSO4), filtered and concentrated under reduced pressure to provide the title compound, which was used without further purification.

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64872; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, belongs to esters-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. category: esters-buliding-blocks

Methyl 3-bromo-2-bromomethylbenzoate A mixture of methyl 3-bromo-2-methylbenzoate (17.0 g, 74.22 mmol) and N-bromosuccinimide (15.85 g, 89.06 mmol) in acetonitrile (200 mL) was heated under gently refluxing for 17 hours while a 200 W bulb situated 2 cm away was shining on the reaction flask. The mixture was cooled to room temperature and solvent was removed. The residue was dissolved in ethyl acetate (200 mL) and washed with water (3*80 mL), brine (80 mL) and dried (MgSO4). Solvent was removed to give methyl 3-bromo-2-bromomethylbenzoate (24.5 g, 97% by HPLC): 1H NMR (CDCl3) delta7.90-7.86 (dd, J=1.0 and 7.9 Hz, 1H), 7.78-7.74 (dd, J=1.2 and 8.2 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 5.12 (s, 2H), 3.95 (s, 3H).

The synthetic route of 99548-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4- hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20 0C. After washing with water (2 X 100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to -10 0C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at – 100C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS {m/z) : 245 (M + l).

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

Reference:
Patent; TRANSTECH PHARMA; WO2008/101914; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics