Tag: M.W=100-200

98298-66-9,Some common heterocyclic compound, 98298-66-9, name is 1-Chloroethyl isopropyl carbonate, molecular formula is C6H11ClO3, 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 Preparation of 1-bromoethyl isopropyl carbonate A solution of 1-chloroethyl isopropyl carbonate (16.7 g; 0.10 mol) and hexabutylguanidinium chloride (0.43 g; 0.0011 mol) in toluene (40 ml) is heated to 115 C. and a gas stream containing 15 g (0.186 mol) of anhydrous hydrobromic acid is passed through it over 7 hours. The reaction medium is degassed with argon, the toluene is removed, the product is distilled under reduced pressure and 16.0 g of the expected product is obtained (Yld=76%).

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 isopropyl carbonate, its application will become more common.

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US5202454; (1993); A;,
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The chemical industry reduces the impact on the environment during synthesis 4518-10-9, name is Methyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life. 4518-10-9

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (101mg, 0.45mmol) and DMAP (8mg, 0.06mmol) and stir for 10min. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J. Am. Chem. Soc.; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1H, J = 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J = 7.8Hz); 7.78 (t, 1H, J = 1.8Hz); 7.90 (dd, 1 H, J1 = 8.1Hz, J2 = 1.3Hz).

The chemical industry reduces the impact on the environment during synthesis 4518-10-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Revotar Biopharmaceuticals AG; EP1764096; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 349-43-9, name is Ethyl 2-fluoropropionate, 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 349-43-9, 349-43-9

Add 12.0 g (0.1 mol) to a 250 ml four-necked flask with a condenserEthyl 2-fluoropropionate,240g of carbon tetrachloride,24.0 g (0.15 mol) of bromine,20.2 g (0.15 mol) of sulfuryl chloride,0.6g azoisobutyronitrile,StirThe reaction was carried out by heating to 70 ¡ãC.After 10 h, the conversion of methyl 2-fluoropropionate was 98.2percent.The selectivity to ethyl 2-fluoro-2-bromopropionate was 88.4percent.

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

Reference:
Patent; Juhua Group Technology Center; Ye Lifeng; Wang Shuhua; (5 pag.)CN104892409; (2018); B;,
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108928-00-3, A common compound: 108928-00-3, name is Ethyl 2,4-difluorobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 30A ethyl 2-(1H-indol-5-yloxy)-4-fluorobenzoate Ethyl 2,4-difluorobenzoate (1.14 g), K3PO4 (1.30 g) and 5-hydroxyindole (0.90 g) were stirred at 110 C. in diglyme (12 mL) for 24 hours. The reaction was cooled and poured into ether. The solution was washed three times with 1M aqueous NaOH solution, and brine, and dried over Na2SO4. The solution was then filtered, concentrated, and the crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes.

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 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
Ester – Wikipedia,
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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. 89-91-8, name is Methyl 2,2-dimethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 89-91-8

Method 1; Ethyl 4,4-dimethoxy-3 -oxobutanoate; To a solution of dimethoxy methyl acetate (25 g, 0.19 mol) in EtOAc (75 ml), was added sodium hydride (8.5 g, 0.21 mol) in portions. After all the sodium hydride was added, the mixture was set to reflux for 10 hours. The reaction mixture was poured onto cold water followed by pH adjustment to 3-4 using 3N HC1 solution. The layers were separated and the organic layer was dried, filtered, and concentrated in vacuo to afford 34 g (96% crude recovery) of the title compound, which was used further without purification.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/8523; (2006); A1;,
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Ester – an overview | ScienceDirect Topics

3196-15-4, These common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, 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 1Preparation of methyl 2-(6-methoxy-lH-inden-3-yl) butanoateAn oven dried 5 -L four-necked round -bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-l-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous TEtaF was stirred at 6O0C (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 74] mmoi) in 400 inL anhydrous TEtaF was added slowly through an addition funnel After completion of the addition, the reaction mixture was stirred at 6O0C (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following IN aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of IN HCl solution. The pot temperature was kept below 2O0C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4, The product (127 g, >;99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-t,) delta 7.28(d, IH), 7.05(d, IH), 6.82(dd, IH), 6.22(s, IH), 3.72(s, 3H), 3.60(m, IH), 3.58(s, 3H), 3.28(s, 2H), 1.95(m, IH), 1.80(m, IH), 0.88(t, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3196-15-4.

Reference:
Patent; DARA BIOSCIENCES, INC.; DELMEDICO, Mary Katherine; WO2010/141696; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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. 369-26-6

Step 1 : 3-Amino-N-(2-tert-butoxyethyl)-4-fluorobenzamide A mixture comprising 2-tert-butoxyethanamine (1 .2 g, 5.12 mmol, 50percentw/w) and methyl 3-amino-4-fluorobenzoate (0.866 g, 5.12 mmol) in THF (10 ml) was treated with TBD (0.713 g, 5.12 mmol) and heated at 90 ¡ãC for 16 hrs. After cooling to RT, the solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic portion was separated and washed with 10percent aq citric acid (x 2), NaHC03(sat. aq), brine, dried (MgS04) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-100percent EtOAc in iso- hexane afforded the title compound as a clear oil;LC-MS: Rt 1.09 mins; MS m/z 255 [M+H]+; Method 2minl_C_v003

Statistics shows that 369-26-6 is playing an increasingly important role. we look forward to future research findings about Methyl 3-amino-4-fluorobenzoate.

Reference:
Patent; NOVARTIS AG; IRM LLC; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon Christopher; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; SVIRIDENKO, Lilya; THOMSON, Christopher; YEH, Vince; JANUS, Diana; WEST, Ryan; WO2013/30802; (2013); A1;,
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Ester – an overview | ScienceDirect Topics

680-65-9, A common compound: 680-65-9, name is Diethyl difluoromalonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

5 g (1.0 eq., 25.49 mmol) of the compound 37 was dissolved in 40 mL of methanol, and 30 mL of methanol solution of sodium hydroxide (1.43 g (1.0 eq., 25.49 mmol)) was added dropwise thereto. It was then stirred for 3 hours at room temperature. After confirming by TLC the disappearance of the reacting materials, benzyl amine (8.4 mL (3.0 eq., 76.47 mmol)) was added and stirred overnight at 55 C. The reaction solution was concentrated under reduced pressure by using an evaporator, and the precipitated solids were added with diethyl ether followed by washing and filtering. The washed solids were dissolved in 1 M HCl. Then, liquid fractionation extraction was performed 3 times using ethyl acetate. The collected organic layer was washed with a saturated aqueous solution of NaCl. After drying over magnesium sulfate, it was concentrated under reduced pressure by using an evaporator in water bath at 40 C. to obtain the residues (compound 39). It was directly subjected to the following reducing reaction.

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, Diethyl difluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seikagaku Corporation; Miyamoto, Kenji; Yasuda, Yosuke; Takeuchi, Hisayuki; Yoshioka, Keiji; (69 pag.)US2016/151506; (2016); A1;,
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Ester – an overview | ScienceDirect Topics

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. 37466-90-3 name is Ethyl 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. 37466-90-3

General procedure: Compound 3 (10 mmol) was dissolved in ethylene glycol (50 mL) andthen compound 2 (10 mmol) and a small amount of polyphosphoricacid were added to the stirred solution which was then refluxed forseveral hours (the reaction was monitored by TLC). On completion ofthe reaction, the mixture was poured into ice water. The solution wastreated with 30% sodium hydroxide to slight alkalinity (pH = 9). Theprecipitated solid was filtered off, recrystallised from ethanol anddried in vacuo to give compound 4.

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

Reference:
Article; Wang, Xinying; Liu, Yizhou; Xu, Juan; Jiang, Fanwei; Kang, Congmin; Journal of Chemical Research; vol. 40; 10; (2016); p. 588 – 590;,
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25597-16-4, 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. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[1051] A mixture of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (1.40 g, 6.51 mmole), K2C03 (1. 80 G, 13.02 mmole), triethylamine (2.63 g, 26.05 mmole), and ethyl 4,4, 4- trifluorocrotonate (4.38 g, 26.05 mmole) in anhydrous DMSO (5.0 mL) was heated to 90 C under a dry N2 atmosphere for 18 hrs. The contents were poured into 2.4 N HCL (50 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give a dark yellow oil which was subject to flash chromatography (silica gel) and eluted with 10% EtOAc in hexanes to give a yellow solid (1.6 g, 68%). GCMS 7N/Z 364.0 (M+). H NMR (CDC13/400 MHz) 7.59 (s, 1H), 7.27 (s, 1H), 7.16 (s, 1H), 5.70 (q, 1H, J=7. 0 Hz), 4.29 (m, 2H), 2.19 (s, 3H), 1.32 (m, 3H).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics