Month: March 2021

Reference of 927-68-4,Some common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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.

Compound 7-1 (200 mg, 0.9 mmol) And sodium hydride (54mg, 1.35mmol) dissolved in 3ml DMF and stirred for 30 minutes, Add 2-bromoethyl acetate (165 mg, 0.99 mmol) in 2 ml of DMF, Stir overnight at room temperature. On the following day, after the reaction was detected by TLC, water was added for extraction. It was washed with saturated brine and dried over anhydrous sodium sulfate. Suction filtration, the filtrate was concentrated under reduced pressure, the crude product was separated by column chromatography, 172 mg of a colorless oil was obtained in a yield of 61%.

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Meng Linghua; Ding Jian; Chen Shulun; Ding Chunyong; Guo Wei; (26 pag.)CN110143955; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 37466-90-3, name is Ethyl 3,4-diaminobenzoate, 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 C9H12N2O2

Preparation of ethyl 2-phenyl-1 H-benzo[d]imidazole-5-carboxylate 4-fluoro-3-nitrobenzoic acid (0.05g, 0.27 mmol) was esterified in the presence of catalytic sulfuric acid in ethanol (10mL) by refluxing at 65 eC for 6 hours. Ammonium hydroxide 28% (0.26 mmol) was subsequently added to the solution, stirred for 0.5 hour, treated with tin (Pi) chloride (190mg, 1 mmol) and stirred for a further 0.5 hour. The resulting mixture was then treated with benzaldehyde (0.3 mmol) and sodium bisulfite (57 mg, 0.3 mmol) and left to stir for another 3 hour. The solution was cooled to room temperature and subsequently evaporated under reduced pressure. It was resuspended in ethyl acetate (10mL), washed with 10% sodium carbonate (20mL) and water (20mL x2), dried over sodium sulfate and concentrated under reduced pressure. The crude products were purified by column chromatography (silica gel, 70- 230 mesh; C HC I3-MeOH 9:1 ) to obtain the final products (70-90%).

The synthetic route of Ethyl 3,4-diaminobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITI SAINS MALAYSIA; OON, Chern Ein; TAN, Soo Choon; YEONG, Keng Yoon; ALI, Mohamed Ashraf; (39 pag.)WO2017/52359; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 36692-49-6, 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. 36692-49-6 name is Methyl 3,4-diaminobenzoate, 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.

Typical procedure: Mix Et3N (2.53 mg, 0.025 mmol), 2-phenylacetaldehyde 1a (30 mg, 0.25 mmol), benzene-1,2-diamine 2a (32.4 mg, 0.3 mmol), in toluene (2.5 mL) under O2 (1 atm). The reaction mixture was stirred at 60 C for 12 h. After cooling down to room temperature and concentrating in vacuum, the residue was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate=20:1) to afford 47 mg (91%) of 3aa.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3,4-diaminobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Chun; Xu, Zejun; Zhang, Liangren; Jiao, Ning; Tetrahedron; vol. 68; 26; (2012); p. 5258 – 5262;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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. SDS of cas: 35450-36-3

A mixture of methyl 2-bromo-5-methoxybenzoate (3.0 g, 12.2 mmol), vinylboronic acid (2.26 g, 14.7 mmol), K2CC>3 (5.08 g, 36.72 mmol) and Pd(dppf)Cl2-DCM (500 mg, 0.61 mmol) in 1,4-dioxane/H2Patent; CTXT PTY LIMITED; STUPPLE, Paul, Anthony; LAGIAKOS, Helen, Rachel; FOITZIK, Richard, Charles; CAMERINO, Michelle, Ang; NIKOLAKOPOULOS, George; BOZIKIS, Ylva, Elisabet, Bergman; KERSTEN, Wilhelmus, Johannes, Antonius; WALKER, Scott, Raymond; HUBERT, Jonathan, Grant; (0 pag.)WO2020/2587; (2020); A1;,
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Ester – an overview | ScienceDirect Topics

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. 7364-20-7, name is Methyl 4-ethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 7364-20-7

Under nitrogen protection, the1-formic acid methyl-4-ethylbenzene1 t (0.5 mmol), NBS (1.25 mmol) and acetonitrile (2 mL) were added to the reaction tube. Stir at 100 C for 12 hours. After stopping the reaction, cool to room temperature, evaporate the solvent and separate by column chromatography. The volume ratio (mL / mL) of the eluent used is ethyl acetate: petroleum ether = 0: 100 ~ 1: 200.1- (4-formic acid methyl) phenyl-1,2-dibromoethane3t, yield is 83%.

According to the analysis of related databases, 7364-20-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute; Qian Bo; Li Weihe; (12 pag.)CN110862292; (2020); A;,
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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 3,4-diaminobenzoate

Ethyl 3,4-diaminobenzoate (25.0 g, 0.139 mol) was dissolved in THF (280 ml_). Triethylamine (23.2 ml_, 0.166 mol) and B0C2O (33.3 g, 0.153 mol, 1.1 eq) were added. Stirred at room temperature for 16 h. The solvent was removed under vacuum and the crude solid triturated in hot diethyl ether/petrol 40-60 (5:95, 500 ml_), filtered, washed with petrol 40-60 (100 ml.) and dried under high vacuum to yield the product as a light brown solid (34.8 g, 89.5%). 1H NMR (400 MHz, chloroform-d) d 7.83 (d, J = 1.9 Hz, 1 H), 7.72 (dd, J = 8.4, 2.0 Hz, 1 H), 6.73 (d, J = 8.4 Hz, 1 H), 6.15 (s, 1 H), 4.30 (q, J = 7.1 Hz, 3H), 4.26 (s, 2H), 1.50 (s, 10H), (0482) 1.35 (t, J = 7.2 Hz, 4H).

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; ZIYLO LTD.; H?EG-JENSEN, Thomas; MADSEN, Alice, Ravn; KRUSE, Thomas; SAUERBERG, Per; MURRAY, Anthony; DAVIS, Anthony, Peter; CHAPMAN, Andy; (0 pag.)WO2020/58322; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18469-52-8, 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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Commercially available methyl bromomethylbenzoate (manufactured by Aldrich Corporation) (10.0 g) was dissolved in DMF (100 ml), and the solution was added with potassium phthalimide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (9.70 g) and the whole was stirred at room temperature for 1.5 hours. After completion of the reaction, the solution was concentrated and added with water, followed by extraction with chloroform. The resultant was washed with a saturated saline solution and dried with anhydrous sodium sulfate, and the solvent was distilled off, thereby obtaining a white solid (12.9 g). Subsequently, 7.56 g of the solid was dissolved in methanol (100 ml), and the solution was added with hydrazine monohydrate (manufactured by Nacalai Tesque, Inc.) (6.25 ml) and the whole was stirred at 60C for 1.5 hours. After completion of the reaction, the precipitated solid was filtrated out and the solvent was distilled off. The resultant was added with water and subjected to extraction with chloroform. The resultant was washed with a 0.3 mol/l sodium hydroxide aqueous solution and a saturated saline solution and dried with anhydrous sodium sulfate, and the solvent was distilled off. Methanol (120 ml) and 2-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (2.35 g) were added to the resultant and the whole was stirred at room temperature for 2 days. After completion of the reaction, the precipitated solid was filtrated out. The liquid layer was concentrated and evaporated to dryness, and washing was performed by adding anhydrous methanol (30 ml). Then, the solid was filtrated out. The resultant solid and the solid that had been previously filtrated out were suspended in methanol (86 ml), and sodium borohydride (1.42 g) was added under ice-cooling. The solution was stirred at room temperature for 1 hour, and the solvent was distilled off. After addition of water, extraction was performed with chloroform, and the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure and drying, thereby obtaining a colorless oily substance (4.32 g). 4.28 g of the oily substance was dissolved in DMF (65 ml), and the solution was added with di-t-butyldicarbonate (8.90 ml) and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off, and the residue was dissolved in chloroform, followed by washing with a saturated saline solution. After drying with anhydrous sodium sulfate, the solvent was distilled off, and THF (43 ml), methanol (43 ml), and a 1 mol/l sodium hydroxide aqueous solution (43 ml) were added to the resultant, followed by stirring at room temperature for 14 hours. After completion of the reaction, the solvent was distilled off, and water (5.0 ml) was added to the resultant. Further, 1 mol/l hydrochloric acid was carefully added to the solution, and the acid-precipitate was filtrated out and dried, thereby obtaining the subject compound (4.87 g) as a white solid. MS(FAB,Pos.):m/z=332[M+H]+

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(aminomethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 135613-33-1, 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. 135613-33-1, name is Ethyl 3-(2-bromophenyl)propanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(b) 2-(2-thiazolinylthio)-hydrocinnamic acid ethyl ester: 1.4 ml of triethylamine are added dropwise to a solution of 1.8 g of 2-mercapto-1,3-thiazoline and 2.6 g of 2-bromo-hydrocinnamic acid ethyl ester in 15 ml of THF and the whole is stirred under reflux for 6 hours. The reaction mixture is filtered, the filtrate is concentrated by evaporation and the residue is partitioned between ethyl acetate and water. The organic phase is washed with water, dried, concentrated by evaporation and purified by chromatography on silica gel with eluant R. Rf (W)=0.67.

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 3-(2-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ciba-Geigy Corporation; US4758584; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, 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. SDS of cas: 89-91-8

Cyclohexanone Compound 2a (1.37 g, 14.0 mMol) in THF (5 mL) was added dropwise to a solution of LHMDS (16.0 mL, 16.0 mMol) in anhydrous THF (25 mL) at -78 C. under a N2 atmosphere. The solution was stirred at -78 C. for about 1 hr. Methyl dimethoxyacetate Compound 11a (1.88 g, 14.0 mMol) in anhydrous THF (5 mL) was then added dropwise. The reaction mixture was stirred while warming to r.t. over a period of about 15 hrs, then the reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford 2-(2,2-dimethoxy-acetyl)-cyclohexanone Compound 11b (1.82 g, 65%). Benzylhydrazine dihydrochloride Compound 11c (1.75 g, 9.00 mMol) and K2CO3 (1.51 g, 10.92 mMol) were added to a solution of Compound 11b (1.80 g, 9.10 mMol) in MeOH (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred overnight while warming to r.t., then the reaction was quenched with water (20 mL). The organic layer was diluted with EtOAc (200 mL) and washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product as an oil. The oil was purified by flash chromatography (eluted with 20% EtOAc in hexane) to afford 1-benzyl-3-dimethoxymethyl-4,5,6,7-tetrahydro-1H-indazole Compound 11d (1.80 g, 70%) as a colorless oil. 3N HCl (8 mL) was added to a solution of Compound 11d (1.70 g, 5.9 mMol) in acetone (50 mL) at 0 C. under a N2 atmosphere. The reaction mixture was stirred for 4 hrs while warming to r.t., then the reaction was quenched with water (20 mL), neutralized to pH 7 with K2CO3 and diluted with CH2Cl2 (100 mL). The organic layer was washed with water and brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford a 1-benzyl-4,5,6,7-tetrahydro-1H-indazole-3-carbaldehyde Compound 11e (1.35 g, 95%) as a colorless oil. Methanesulfonyl chloride Compound 11f1 (2.0 g, 17 mMol) and TEA (2.43 mL, 17.46 mMol) were added to a solution of (1R)-1-phenyl-ethylamine Compound 11f2 (1.75 g, 17.5 mMol) in CH2Cl2 (50 mL) at 0 C. under a N2 atmosphere. The mixture was stirred for 3 hrs while warming to r.t., then the reaction was quenched with water (5 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to afford the corresponding N-(1-phenyl-ethyl)-methanesulfonamide Compound 11f3 as an oil. (Boc)2O (di-tert-butyldicarbonate) (4.57 g, 21.0 mMol) and DMAP (8 mg) were added to a solution of the methanesulfonamide Compound 11f3 in CH2Cl2 (10 mL) at 0 C. under a N2 atmosphere. The mixture was stirred overnight while warming to r.t., then the reaction was quenched with a saturated solution of NaHCO3 (sodium bicarbonate) (10 mL). The organic layer was diluted with CH2Cl2 (100 mL) and then washed with water and brine. The organic layer was separated, dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude Boc-protected methanesulfonamide product. The product was purified by flash chromatography (eluted with 10% EtOAc in hexane) to afford (methylsulfonyl)[(1R)-1-phenyl-ethyl]-carbamic acid tert-butyl ester Compound 11f (3.89 g, 80%) as a colorless oil. Adapting a published procedure (Tozer M J, Woolford A J A and Linney I A, Synlett, 1998, 2, 186-188) to obtain the target compound, a 1M solution of KOtBu (potassium tert-butoxide) in THF (0.75 mL, 0.75 mMol) was added dropwise to a solution of the ester Compound 11f (0.070 g, 0.250 mMol) in anhydrous THF (5 mL) at -78 C. under a N2 atmosphere. After 45 min, Compound 11e (0.060 g, 0.250 mMol) diluted in THF (3 mL) was added dropwise. The solution was reacted over a 15 hr period while warming to ambient temperature. The reaction was quenched with water (5 mL). The organic layer was diluted with EtOAc (100 mL) and then washed with water and brine. The organic layer was separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. The product was purified by flash chromatography (eluted with 20% EtOAc in hexane) to give Compound 260 (0.079 g (75%), as a white solid. MS m/z 422 (MH+); 1H NMR (CDCl3, 400 MHz) delta 7.56 (d, J=15.5 Hz, 11H), 7.35-7.19 (m, 8H), 7.11-7.09 (m, 2H), 6.42 (d,J=15.5 Hz, 1H), 5.21 (s, 2H), 4.61-4.11 (m, 2H), 2.45-2.41 (m, 2H), 2.36-2.33 (m, 2H), 1.75-1.67 (m, 4H), 1.55 (d, J=6.5 Hz, 3H).

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

Reference:
Patent; Lagu, Bharat; Liotta, Fina; Pan, Meng; Wachter, Michael P.; Xia, Mingde Xia; US2005/228034; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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. Product Details of 41841-16-1

A solution of methyl 2-(4-bromophenyl)acetate (6g, 30mmol) in tetrahydrofuran (67.2ml, 0.39/W) was added 1 M potassium t-butoxide in tetrahydrofuran (57.6ml, 57.6mmol). Reaction mixture was cooled to 00C and methyl iodide (3.59ml, 57.6mmol) was added drop wise. After addition was complete, reaction was slowly warmed up to room temperature and stirred for 16 hours. Reaction mixture was then carefully quenched with 1 M hydrochloric acid and concentrated. Reaction was diluted with water and extracted with ethyl acetate. Pooled organics were washed with water and brine and then dried over sodium sulfate, filtered and concentrated to give a crude dark oil. Crude product purified on silica gel eluting with 0%-5% ethyl acetate in heptane to give methyl 2-(4-bromophenyl)-2-methylpropanoate (1 D-1 ) (6.44g, 92%) as a yellow oil 1 H NMR (400 MHz, CHLOROFORM-d) d ppm 1.54 (s, 6 H) 3.63 (s, 3 H) 7.19 (d, J=8.78 Hz, 2 H) 7.43 (d, J=8.98 Hz, 2 H)MS(LC-MS) 371.2 (M+1 )

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics