Month: May 2021

These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, 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. Formula: C9H10BrNO2

Example 18:Methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoateTo a solution of the compound of example 17 (15 g, 61.5 mmol) in DOE (100 ml) were added dihydro-2H-pyran-4(3H)-one (11.35 mL, 123 mmol) and acetic acid (21 .11 mL, 369 mmol) and stirred at RT for 2h. The reaction mass was cooled to 0 00 and sodium triacetoxyborohydride (39.1 g, 184 mmol), was addedlot wise in 1 h which was left to stir at RT for 16h. After completion of the reaction, water was added and extracted with ethyl acetate. The compound was adsorbed on silica and purified by column chromatography (silica gel, 10-80 % ethyl acetate in petroleum ether) to yield the title compound.Yield: 15.1 g (73.6 %); 1H NMR (DMSO-d6, 300 MHz): 66.97-6.93 (m, 2H),3.87-3.85 (m, 2H), 3.80 (5, 3H), 3.59-3.55 (m, 1H), 3.46-3.41 (m, 2H), 2.14 (5,3H), 1.84-1.82 (m, 2H), 1.56-1.53 (m, 2H);MS (ESl+): m/z 329.1 [M+H] HPLO Purity: 98.3 %.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GUPTE, Amol; KANDRE, Shivaji; GADEKAR, Pradip, Keshavrao; CHAVAN, Sambhaji; JADHAV, Ravindra, Dnyandev; THAKRE, Gajanan, Amrutrao; BAJAJ, Komal; JANRAO, Ravindra, Ashok; DEHADE, Amol; GAIKWAD, Nitin; KADAM, Kishorkumar; MORE, Tulsidas, Sitaram; GUHA, Tandra; SEELABOYINA, Balapadmasree; SABLE, Vikas, Vasant; WO2015/110999; (2015); A1;,
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Synthetic Route of 50893-36-2,Some common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, molecular formula is C5H9ClO3, 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 4 Preparation of ethyl N,N-di-n-butylcarbamate To a solution of 6.5 g (0.05 mole) of di-n-butylamine and 5.56 g (0.055 mole) of triethylamine in 40 ml of THF, 8.4 g (0.055 mole) of alpha-chloroethyl ethyl carbonate dissolved in 10 ml of THF are added dropwise and with stirring while the temperature is maintained at 5¡ã-10¡ã C. The mixture is allowed to return to room temperature, and is maintained with stirring at this temperature for 2 hours. After removal of the precipitate by filtration, evaporation of the solvent and distillation under reduced pressure, 6.3 g (63percent yield) of the expected carbamate are collected. B.p. 76¡ã C./26.6 Pa (0.2 mm Hg).

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

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US4725680; (1988); A;,
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Electric Literature of 126430-46-4, These common heterocyclic compound, 126430-46-4, name is Benzyl 4-bromobutanoate, 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.

REFERENCE EXAMPLE 26 A mixture of benzyl 4-bromobutanoate (58.6 diethylamine (58.3 g) and dichloromethane (1000 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate gave benzyl 4-(N,N-diethylamino)butanoate (33.8 g, 60%). NMR (delta ppm in CDCl3): 0.99 (6H,t,J=7.2 Hz), 1.78 (2H,quintet,J=7.2 Hz), 2.39 (2H,t,J=7.2 Hz), 2.49 (4H,q,J=7.2 Hz), 5.11 (2H,s), 7.30-7.41 (5H,m).

The synthetic route of 126430-46-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5650410; (1997); A;,
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Synthetic Route of 91-44-1, 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 91-44-1 as follows.

To a 50 mL round bottom flask containing acetonitrile (20 mL) was added 7-(diethylamino)-4-methylcoumarin (1.01 g, 4.37 mmol). Then N-bromosuccinimide (0.86 g, 4.8 mmol) was added in portions. After stirring at room temperature for 23 h, the reaction mixture was poured into water after the reaction was completed. The organic phase was extracted three times with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed by evaporation to give a yellow powder.

According to the analysis of related databases, 91-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Song Huacan; Cao Wenyan; Song Senchuan; Liu Jiarong; (18 pag.)CN109574942; (2019); A;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H16O3

Compound 300.1. Ethyl 4-methoxycyclohexanecarboxylate. Into a 100-mL round- bottom flask, was placed a solution of ethyl 4-hydroxycyclohexane-l-carboxylate (1 g, 5.81 mmol) in tetrahydrofuran (20 mL). Sodium hydride (349 mg, 8.72 mmol, 60percent) was added to the reaction at 0 ¡ãC in portions, then stirred for 20 min. This was followed by the addition of CH3I (865 mu, 11.6 mmol) at 0 ¡ãC. The reaction mixture was stirred overnight at room temperature, quenched with 6 mL of brine and extracted with 3 x 40 mL of ether. The combined organic layers were washed with 2 x 20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 800 mg (74percent) of the title compound as a colorless oil.

According to the analysis of related databases, 3618-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); 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. 111-61-5, name is Ethyl stearate, A new synthetic method of this compound is introduced below., SDS of cas: 111-61-5

Example 5 Production of Octadecanedioic Acid (?ODDA?) by an Engineered Microorganism (0063) A one milliliter frozen glycerol stock of Candida sp. yeast strain sAA2178 (disclosed in international patent application PCT/US2013/076664) was inoculated into a 500 ml baffled flask containing about 80 ml of SP92 culture medium (described in Example 2 above) under sterile conditions, and the flask was capped with a foam plug and placed on a shaker at 30 C. and 250 rpms for about 24 hours. This culture was used to inoculate three 500 ml baffled flasks containing about 80 ml of SP92 culture medium at a starting optical density of 600 nm of 0.4. The flasks were incubated at 24 hours at about 30 C. and 250 rpm after which the three flasks were combined. This combined culture was divided into three aliquots which were used to inoculate three containing 2.5 L baffled flasks containing SP92 (75 g/L dextrose) and having initial optical density of 600 nm of 2; these flasks were incubated for about 24 hrs at about 30 C. and 250 rpms. (0064) These cultures were used to inoculate about 200 L of 1.5¡ÁKA media (described in Example 2) containing about 40.5 g/L of dextrose in a 300 L working volume stir tank fermenter. The fermenter was kept at about 34 degrees Celsius, agitation was kept at about 400 rpm, the airflow was about 1 VVM and the pH was set at about 5.8 using NaOH as base. Once dextrose was depleted the pH was increased to 6.0, glucose and ethyl-stearate mixture (74% ethy-stearate, 18% stearic acid, 8% methyl stearate) were each fed into the fermenter at about 1.35 g/L-h and 0.9 g/L-h respectively for the duration of the 100 hour fermentation, however from hour 40 through hour 48, the rate of ethyl stearate mixture was increased to 1.8 g/L hr. The resulting broth had a concentration of dodecanedioic acid of about 40 g/L as determined by GC analysis.

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; Verdezyne, Inc.; LAPLAZA, Jose; US2015/361024; (2015); A1;,
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These common heterocyclic compound, 2177-70-0, name is Phenyl methacrylate, 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. Computed Properties of C10H10O2

Comparative Example 2 After the dropwise addition of phenyl methacrylate, N,N,N’,N’-tetramethylethylene diamine was not added, and otherwise the reaction was carried out in the same manner as in Example 7, an organic layer was obtained. As a result of gas chromatographic analysis of the organic layer, the yield of the desired 1,3,3,5-tetramethylcyclohexyl methacrylate was found to be less than 1 mol %.; Example 7 2.5 mL of tetrahydrofuran solution of 3.0 mol/L concentration of methylmagnesium chloride was added to 10 mL of anhydrous tetrahydrofuran in a reaction vessel under an atmosphere of argon, and then 1.0 g of 3,3,5-trimethylcyclohexanone was added with stirring while the mixture in the reaction vessel was kept at a temperature of 50 C. or less, followed by stirring for another one hour at the same temperature with stirring. Then, 1.20 g of phenyl methacrylate was added drop wise into the reaction vessel, and then 1.74 g of N,N,N’,N’-tetramethylethylene diamine, and the reaction was carried out with stirring for 24 hours at a temperature of 60 C. After the reaction, an aqueous saturated solution of ammonium chloride was added to the resulting reaction mixture, and the desired product was extracted with ethyl acetate. The obtained organic layer was subjected to gas chromatographic analysis. As a result, the yield of 1,3,3,5-tetramethylcyclohexyl methacrylate was found to be 18.0 mol %.

The synthetic route of Phenyl methacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HONSHU CHEMICAL INDUSTRY CO., LTD.; US2006/167305; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2216-94-6, name is Ethyl phenylpropiolate, 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 2216-94-6, Formula: C11H10O2

General procedure: In a flame-dried Young-tube ethyl 3-arylpropiolate (16, 1.00 eq.), arylboronic acid (3.00 eq.) and CuOAc (2 mol%) were dissolved in MeOH (0.5 M). The solution was degassed by three freeze-pump-thaw cycles and then stirred over night at room temperature. The resulting suspension was filtered over celite and the solvent was removed under reduced pressure. Purification by column chromatography (Si02, 5 x 20 cm, eluent as listed for the Revalue) afforded the desired ethyl 3,3-diarylacrylate.’

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 phenylpropiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ebner, Christian; Pfaltz, Andreas; Tetrahedron; vol. 67; 52; (2011); p. 10287 – 10290;,
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Related Products of 18595-12-5, A common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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 82; Preparation of inhibitor methyl 5-(5-(4-((4~methyipiperazin-1-yl)methyl)- benzamido)-2-methylbenzamido- 1 H-pyrro/o/2, 3-b]pyridine-2-carboxylate (ND0117); Step 1 : Preparation of methyl5-(4-(chloromethyl)benzamido)-2-methylbenzoate; A reactor is charged with 1g (6.06 mmol) of methyl 3-amino-6-methylbenzoate and 1.2g (119 mmol) of triethylamine in 25 ml of dichloromethane. 1.145g (6.05 mmol) of 4-chioromethylbenzoyle chloride is then added and the mixture is stirred at room temperature for 2 hours. The reacting medium is then washed with 10 ml of a saturated NaHCO3 solution, 10 ml of water and 10 ml of a saturated NaCI solution. The organic phase is dried, evaporated and the obtained residue is triturated in ethylic ether and then in pentane to give a white solid (1.2 g, 66%).

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; NOVA DECISION; AZASYNTH; YASRI, Abdelaziz; CHEVE, Gwenael; BORIES, Cedric; DELON, Louis; WO2010/92489; (2010); A1;,
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Synthetic Route of 61644-18-6, 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. 61644-18-6, name is Chloromethyl isobutyrate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Alternatively, a mixture of chioromethyl 2-methyl- propanoate (1.0 eq), fumaric acid (5.0 g, 1.0 eq), and DIEA (2.0 eq) was stirred between 50 to 70 C. overnight. The reaction was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over Na2504, filtered and concentrated in vacuo to yield the crude product. The crude material was then purified by silica gel column chromatography using dichloromethane and methanol to yield compound (6b).

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, Chloromethyl isobutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nguyen, Mark Quang; (47 pag.)US2016/229819; (2016); A1;,
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Ester – an overview | ScienceDirect Topics