Tag: M.W=100-200

Synthetic Route of 50893-36-2, The chemical industry reduces the impact on the environment during synthesis 50893-36-2, name is 1-Chloroethyl ethyl carbonate, I believe this compound will play a more active role in future production and life.

EXAMPLE 119B 1-(Ethyloxycarbonyloxy)ethyl 4-{N-butyl-N-[(2′-[N-triphenylmethyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine-5-carboxylate The compound resulting from Example 119A (1.00 g, 1.5 mmol) was dissolved in anhydrous dimethylformamide (3 mL) and potassium carbonate (616 mg, 4.5 mmol), 1-chloroethyl ethyl carbonate (460 mg, 3 mmol), sodium iodide (450 mg) and triethylamine (5 drops) were added. After stirring at ambient temperature for 30 hours, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and sodium carbonate, and concentrated under reduced pressure. Chromatography eluding with ethyl acetate/hexane mixtures provided the title compound as an amorphous solid (470 mg, 40percent).

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, 1-Chloroethyl ethyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Laboratories; US5250548; (1993); A;,
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Adding a certain compound to certain chemical reactions, such as: 122-72-5, name is 3-Phenylpropyl Acetate, 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 122-72-5, Safety of 3-Phenylpropyl Acetate

(b) 3-(p-Iodophenyl)Propanol Using the procedure outlined in Example 1, 3-phenyl propyl acetate was converted to 3-(p-iodophenyl)propanol (ND25 =1.6048).

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, 3-Phenylpropyl Acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lafayette Pharmacal Inc.; US4175544; (1979); A;,
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Related Products of 61644-18-6, 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. 61644-18-6 name is Chloromethyl isobutyrate, 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: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Chloromethyl isobutyrate, and friends who are interested can also refer to it.

Reference:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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Adding a certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, 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 6065-82-3, Product Details of 6065-82-3

Nine reactions were carried out in parallel and combined for work-up. A solution of 32 1-bromo-3,5-difluorobenzene (100 g, 518 mmol) in 15 THF (700 mL) was degassed and purged with 33 nitrogen three times. Then 2 M 34 LDA (311 mL) was added at -70 C. and the reaction mixture was stirred at -70 C. for 0.5 h under nitrogen. A solution of 35 ethyl 2,2-diethoxyacetate (96 g, 544 mmol) in THF (200 mL) was added drop-wise at -70 C. under nitrogen and the reaction mixture was stirred for 1 h. The reactions were combined and poured into ice saturated 36 ammonium chloride (10 L) in portions and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (5 L), dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluted with petroleum ether EtOAc 1:0-100:1) to give the 37 title compound (1.26 kg, 84% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.12 (d, J=7.2 Hz, 2H), 5.15 (s, 1H), 3.61-3.7 (m, 4H), 1.2 (t, J=7.2 Hz, 6H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); 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. 52449-43-1, name is Methyl 4-chlorophenylacetate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

a) At 35 C. a solution of 4-chlorophenylacetic acid methyl ester (52 g) in THF (170 ml) was carefully added over a period of 70 min to a suspension of NaH (15.6 g) in dry THF (550 ml). Stirring was continued for 40 min without heating and the temperature dropped to 290C. The evolution of gas had stopped before dimethylcarbonate (94.8 ml) was added dropwise while the temperature of the mixture was maintained at 25-28 C. After the evolution of gas had ceased, the mixture was diluted with THF (200 ml) and stirring was continued for 72 h at rt. The mixture was carefully acidified with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in diethyl ether (1200 ml), washed three times with 1 N aq. HCl and once with brine, dried over MgSO4 and evaporated. The residue formed was collected, washed with diethyl ether and dried to give 2-(4-chloro-phenyl)-malonic acid dimethyl ester (42 g) as white crystals.

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; Weller, Thomas; Bolli, Martin; Boss, Christoph; Clozel, Martine; Fischli, Walter; US2004/102464; (2004); A1;,
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Synthetic Route of 10602-03-6, A common heterocyclic compound, 10602-03-6, name is Ethyl 4-ethynylbenzoate, molecular formula is C11H10O2, 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.

Step 3-Preparation of 4-[1-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-3-ylethynyl]-benzoic acid ethyl ester 135 1-Benzenesulfonyl-5-(3,4-dimethoxy-phenyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine (0.0800 g, 0.000151 mol), 4-Ethynyl-benzoic acid ethyl ester (0.0321 g, 0.000181 mol), Bis(triphenylphosphine)palladium(II) chloride (0.0048 g, 0.0000069 mol), and Copper(I) iodide (0.00024 g, 0.0000013 mol) were dissolved in Triethylamine (0.8 mL, 0.005 mol) under an atmosphere of Nitrogen. The resulting mixture was heated to 60 C. and stirred under an atmosphere of Nitrogen for 2 hours. The reaction mixture was was concentrated under reduced pressure and water (30 mL) was added to the residue. This slurry was extracted with ether. (20 mL 2*). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by chromatography (Silica gel, ethyl acetate/hexanes to give 85 mg of the titled product as a pale orange solid. MS(ESI) [M+H+]+=567.10

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; Ibrahim, Prabha N.; Bremer, Ryan; Gillette, Sam; Cho, Hanna; Nespi, Marika; Mamo, Shumeye; Zhang, Chao; Artis, Dean R.; Lee, Byunghun; Zuckerman, Rebecca; US2006/100218; (2006); A1;,
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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 25662-28-6 as follows. Safety of Methyl 1-cyclopentene-1-carboxylate

EXAMPLE 37; N-((lR)-l-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-2- fluoro- 1 -hydroxy cyclopentanecarboxamide; Methyl cyclopent-1-ene-l-carboxylate (30.0 g, 237.8 mmol) was dissolved in 20 mL of dichloromethane and 3-chloroperbenzoic acid (64.4 g, 373.3 mmol) was added. The reaction was allowed to stir vigorously for 2 hours. The reaction mixture was diluted with EtOAc and washed with 0.5 NNuaOEta. The organic layer was dried over sodium sulfate, filtered and concentrated to give 48.0 grams of methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate. Methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate (2.10 g, 14.8 mmol) and N,N-diethyl- ethanamine trihydrofluoride (4.76 g, 29.5 mmol) were heated in a sealable Emrys microwave vessel with stir bar a microwave reactor at 180 0C for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was further washed with water and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude oil, which was subjected to chromatography on silica gel eluting with 0 to 25% EtOAc in hexanes to afford racemic trans methyl^-fluoro-l-hydroxycyclopentanecarboxylate.The racemic trans methyl-2-fluoro-l-hydroxycyclopentanecarboxylate (0.285 g, 1.76 mmol) was dissolved in 21.3 mL of a 4:1 solution of TEtaF:deionized water. A solution of 1 NNaOH was added to the reaction mixture, which was stirred for 1.5 hours. The reaction was acidified with 6 NHCl and extracted with EtOAc three times. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid as a colorless oil.To a mixture of the compound of Reference Example 4 (0.215 g, 6.13 mmol), racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid (90.8 mg, 0.61 mmol), and (lH-l,2,3-benzotriazol- l-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (0.380 g, 0.86 mmol) in 3 mL of dichloromethane was added triethylamine (0.155 g, 1.53 mmol). This reaction mixture was allowed to stir at ambient temperature for 1 hour. The reaction mixture was washed with water, 0.25 NEtaC1, and EPO saturated aqueous sodium bicarbonate solution prior to drying over sodium sulfate. Filtration and solvent removal provided material which was subjected to chromatography on silica gel eluting with 0-40% EtOAc in hexanes to give a mixture of the two diastereomers. Subsequent preparatory TLC eluting with 40% EtOAc in hexanes yielded the title compound. Less polar diastereomer (beige solid): mass ion (ES+) of 481.0 for M+H+: 1H NMR (500 MHz, CDCI3) delta 8.11 (s, IH), 7.66 (bs, NH), 7.35 (d, J= 2.0Hz, IH)5 7.34-7.25 (m, 2H), 5.48 (quint, J= 6.8 Hz, IH), 4.71 (dd, J= 3.9 Hz, J= 53.0 Hz, IH), 4.33 (s, 3H), 4.20 (s, OH), 2.19-2.16 (m, 2H), 1.99-1.92 (m, 4H), 1.467 (d, J= 6.8 Hz, 3H). More polar diastereomer: mass ion (ES+) of 481.0 for M+H+-‘ 1H NMR (500 MHz, CDCI3) delta 8.13 (s, IH), 7.483 (bs,NH), 7.35 (d, J= 9.0 Hz, IH), 7.28-7.24 (m, 2H), 5.47 (m, IH), 4.79 (dd, J= 3.4 Hz, J= 53.0 Hz, IH), 4.34 (s, 3H), 4.23 (s, OH), 2.26-1.91 (m, 6H), 1.46 (d, J= 6.6 Hz, 3H).

According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/132837; (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. 87-24-1, name is Ethyl 2-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-methylbenzoate

A solution of ethyl 2-toluate (17, 41.2 g, 0.25 mole) in carbon tetrachloride (200 mL) was added dropwise to a stirring mixture of benzoyl peroxide (100 mg), carbon tetrachloride (200 mL), and NBS (44.5 g, 0.25 mole) at 0 C. The mixture was heated at reflux for 3.5 hr under nitrogen, and allowed to cool to room temperature overnight. The precipitated succinimide was removed by filtration and the filter cake was washed with carbon tetrachloride. The combined filtrates were washed successively with 2 N NaOH (100 mL), and water (2*100 mL), and the solution was dried over anhydrous MgSO4, filtered (Celite), and evaporated under vacuum to yield an oil. Drying under high vacuum overnight afforded 60.5 g (99%) of compound 18: 1H NMR of the product showed the presence of ca. 15% of unreacted 17. The mixture was used in the next step without further purification: 1H NMR (CDCl3) delta 1.43 (t, J=7 Hz, 3H, CH2 CH3), 4.41 (q, J=7 Hz, 2H, CH2CH3), 4.96 (s, 1H, CH2Br), 7.24 (m, 1H, ArH), 7.38 (m, 1H, ArH), 7.48 (m, 2H, ArH).

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; DarPharma, Inc.; US2007/155720; (2007); 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. 56525-63-4, name is Methyl 3-chloro-4-methylbenzoate, A new synthetic method of this compound is introduced below., name: Methyl 3-chloro-4-methylbenzoate

To a solution of methyl 3-chloro-4-methylbenzoate (5.0g, 27.1mmol) in carbon tetrachloride (50ml) were added NBS (5.8g, 32.0mmol) and AIBN (0.442g, 2.70mmol). The mixture was stirred at reflux for 18h. The mixture was al­lowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96g (84%).

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; FERRING B.V.; WO2006/18443; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 41658-03-1,Some common heterocyclic compound, 41658-03-1, name is Ethyl 3-bromopropiolate, molecular formula is C5H5BrO2, 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.

General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added ethyl 3-bromopropynoate (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-bromopropiolate, its application will become more common.

Reference:
Article; Chang, En-Chiuan; Wen, Ya-Lan; Chang, Chun-Hsi; Shen, Yun-Hwei; Wen, Shaw-Bing; Yeh, Mou-Yung; Wong, Fung Fuh; Tetrahedron; vol. 68; 29; (2012); p. 5920 – 5924;,
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