Category: 4254-15-3

4254-15-3,A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, 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.

Under an atmosphere of argon, trifluoromethanesulfonic acid (485 muEpsilon; 822 mg; 5.47 mmol; 5.0 eq) was added dropwise at 0-5¡ãC (ice/brine bath) to a solution of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5- fluoroimidazol-l-yl)ethanone (400 mg ; 1.09 mmol) and (2S)-propane-l,2-diol (3.33 g; 43.8 mmol; 40.0 eq) in anhydrous toluene (3.0 mL). The resulting mixture was allowed to warm up to room temperature, then refluxed for 20h. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, the combined organic layers were – – dried (MgSO i) and concentrated to dryness in vacuo. The residue was purified by chromatography over silica gel, eluted with a mixture of dichloromethane/methanol (100:0 to 90: 10). Evaporation of the solvents in vacuo afforded 271 mg (54percent) of l-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2- yl]methyl]-5-fluoro-imidazole (approx. 59:41 mixture of diastereoisomers) as a colourless solid. MS (ESI): 423.1 ([M+H]+)

The chemical industry reduces the impact on the environment during synthesis, 4254-15-3,(S)-Propane-1,2-diol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

Compound M31:; To a solution of (S)-1 ,2-propandiol (5 mmol) in 5 ml_ of anhydrous CH2CI2 were added 2-methyl-1-butene (5.5 mmol) and BF3 etherate (0.5 mmol) at room temperature. The stirring was continued for another 24 h. The solvent was removed by vacuum, and the residue was purified by chromatograph on silica gel to afford intermediate (4 mmol, 80 percent yield) as oil. Then, to a suspension of this intermediate and imidazole (6 mmol) in 6 ml_ of anhydrous THF was added 4.8 mL of TBDMSCI (1 M in THF) at 0 0C. The solvent was removed by vacuum, and the residue was re-dissolved in Et2O. The heterogeneous mixture was filtered over a pad of Celite. The filtrate was washed with 1N HCI, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed to give pure M31 (0.34 mmol, 85percent yield) as oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4254-15-3, and friends who are interested can also refer to it.

Reference£º
Patent; UNIVERSITY OF CONNECTICUT; WO2006/44381; (2006); A2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

Compound M31:; To a solution of (S)-1 ,2-propandiol (5 mmol) in 5 ml_ of anhydrous CH2CI2 were added 2-methyl-1-butene (5.5 mmol) and BF3 etherate (0.5 mmol) at room temperature. The stirring was continued for another 24 h. The solvent was removed by vacuum, and the residue was purified by chromatograph on silica gel to afford intermediate (4 mmol, 80 percent yield) as oil. Then, to a suspension of this intermediate and imidazole (6 mmol) in 6 ml_ of anhydrous THF was added 4.8 mL of TBDMSCI (1 M in THF) at 0 0C. The solvent was removed by vacuum, and the residue was re-dissolved in Et2O. The heterogeneous mixture was filtered over a pad of Celite. The filtrate was washed with 1N HCI, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed to give pure M31 (0.34 mmol, 85percent yield) as oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. (S)-Propane-1,2-diol, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; UNIVERSITY OF CONNECTICUT; WO2006/44381; (2006); A2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

The four (4) step reaction sequence starting from 103-1 and 103-2 (prepared as shown from S-(+)-1,2-propanediol (103-0)) provided Boc-T103a in a very good overall yield of 85%. The alternatively protected analogue Ddz-T103a was prepared using the same procedure with an overall yield of 55% [1.4 g Ddz(2RMe)opy18 was obtained starting from 1 g (5.8 mmol) of 103-1]. Synthesis of the Boc-T103b stereoisomer proceeds similarly, but starting from R-(-)-1,2-propanediol.TLC: Rf: 0.3 (100% EtOAc)

According to the analysis of related databases, (S)-Propane-1,2-diol, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Tranzyme Pharma Inc.; US2008/194672; (2008); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

4254-15-3,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. (S)-Propane-1,2-diol,4254-15-3, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 45percent solution of hydrogen bromide in acetic acid (33.0 g, 23.2 mL) was added dropwise over 10 min to 60.3 mmol optically active diol 4a-f with stirring and ice-cooling. The solution was stirred at 0 ¡ãC for 5 min, and next at room temperature for 45 min. Next, water (100 mL) was added, and the mixture was alkalized to pH 8 with solid Na2CO3. The solution was immediately extracted with ethyl ether (5 .x. 60 mL), and the combined extracts were dried over anhydrous Na2SO4. The ether was evaporated, and the product was distilled under reduced pressure or purified by silica gel column chromatography with gradient AcOEt-hexane 9:1.

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, 4254-15-3.

Reference£º
Article; Poterala, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 22; 3; (2011); p. 294 – 299;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 4254-15-3,4254-15-3

(S)-(+)-1,2-propanediol (2.506 g, 32.9 mmol) and 4-methylbenzene-1-sulfonyl chloride (6.91 g, 36.2 mmol) in dichloromethane (DCM) (80 mL) Medium solution,Triethylamine (6.89 mL, 49.4 mmol),Subsequently 4-dimethylaminopyridine (0.201 g, 1.647 mmol) was added.The reaction was stirred at room temperature for 16 hours.The reaction was quenched with saturated aqueous ammonium chloride (20 mL) and the layers were separated.Extract the aqueous portion with DCM (2 ¡Á 20 mL),The combined organic layers were washed with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL).The organic portion is dried over MgSO4, filtered,Concentrate under reduced pressure to give a residue that isPurification by silica gel chromatography eluting with 10-100% ethyl acetate: heptane gave the product (4.56 g, 60% yield).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4254-15-3.

Reference£º
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, 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. 4254-15-3

Example 29; N-r(2Z)-3-butviri.31thiazolor4.5-clpyridin-2(3H)-ylidenel-2-(r(2S)-2-hvdroxypropylloxyl-5 -(trifluoromethyl)benzamide; (S)-propane-l,2-diol (52 mg, 0.68 mmol) in THF (1 mL) was treated with NaH (60percent dispersion; 27 mg, 0.68 mmol) at room temperature for 20 minutes. The mixture was cooled to O0C and a solution of Example 2OB (90 mg, 0.23 mmol) in THF (1 mL) was added. The mixture was allowed to warm to room temperature, and stirred for 4 hours. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography using an Analogix.(R). Intellifiash280 .(TM). (SiO2, 0-100 percent ethyl acetate in hexanes) to afford 19 mg (19percent) of the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 1.04 (t, J=7.48 Hz, 3 H) 1.28 (d, J=6.41 Hz, 3 H) 1.47 – 1.59 (m, 2 H) 1.88 – 1.98 (m, 2 H) 3.87 (t, J=8.85 Hz, 1 H) 4.21 – 4.31 (m, 1 H) 4.35 (dd, J=9.15, 2.75 Hz, 1 H) 4.51 – 4.59 (m, 2 H) 7.12 (d, J=8.85 Hz, 1 H) 7.72 (dd, J=8.54, 2.14 Hz, 2 H) 8.51 (d, J=I.83 Hz, 2 H) 8.75 (s, 1 H); MS (DCI/NH3) m/z 454 (M+H)+., 4254-15-3

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Propane-1,2-diol,4254-15-3,its application will become more common.

Reference£º
Patent; ABBOTT LABORATORIES; FROST, Jennifer, M.; LATSHAW, Steven, P.; DART, Michael, J.; CARROLL, William, A.; PEREZ-MEDRANO, Arturo; KOLASA, Teodozyj; PATEL, Meena; NELSON, Derek, W.; LI, Tongmei; PEDDI, Sridhar; WANG, Xueqing; LUI, Bo; WO2010/71783; (2010); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

4254-15-3,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.4254-15-3,A new synthetic method of this compound is introduced below.

Example 18C N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-{[(2S)-2-hydroxypropyl]oxy}-5-(trifluoromethyl)benzamide (S)-propane-1,2-diol (52 mg, 0.68 mmol) in THF (1 mL) was treated with NaH (60percent dispersion; 27 mg, 0.68 mmol) at room temperature for 20 minutes. The mixture was cooled to 0¡ã C. and a solution of Example 18B (90 mg, 0.23 mmol) in THF (1 mL) was added. The mixture was allowed to warm to room temperature, and stirred for 4 hours. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2.x.30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography using an Analogix.(R). Intelliflash280.(TM). (SiO2, 0-100percent ethyl acetate in hexanes) to afford 19 mg (19percent) of the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 1.04 (t, J=7.48 Hz, 3H) 1.28 (d, J=6.41 Hz, 3H) 1.47-1.59 (m, 2H) 1.88-1.98 (m, 2H) 3.87 (t, J=8.85 Hz, 1H) 4.21-4.31 (m, 1H) 4.35 (dd, J=9.15, 2.75 Hz, 1H) 4.51-4.59 (m, 2H) 7.12 (d, J=8.85 Hz, 1H) 7.72 (dd, J=8.54, 2.14 Hz, 2H) 8.51 (d, J=1.83 Hz, 2H) 8.75 (s, 1H); MS (DCI/NH3) m/z 454 (M+H)+.

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, (S)-Propane-1,2-diol.

Reference£º
Patent; ABBOTT LABORATORIES; US2011/144165; (2011); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

(1) Feeding800 kg of S-propylene glycol, 1600 kg of dimethyl carbonate and 8 kg of sodium methoxide solution were added to the reaction vessel, and heating and stirring were started.The sodium methoxide solution is a 30percent sodium methoxide/methanol solution;The S-propanediol has a propylene glycol content of 99.5percent, a moisture content of 0.5percent, and a specific rotation of ?16.80-17. (2) Temperature rise reactionFirst stage heating reaction The temperature is raised to 60-65 ¡ã C, at which time a solution (mainly methanol, a small portion of dimethyl carbonate) is distilled off, received in the receiving tank, and the solution is evaporated; Second stage heating reactionThereafter, after about 12 hours, the temperature is raised from 65 ¡ã C to 90 ¡ã C, the solution is kept distilled, and the product is distilled as a by-product alcohol-based fuel (methanol and dimethyl carbonate); Third stage temperature rise reactionHeating was continued, and the temperature was raised from 90 ¡ã C to 115 ¡ã C for 8 hours, and the heating was stopped. (3) Cooling downThe temperature was lowered from 115 ¡ã C to 60 ¡ã C. The temperature in the reaction vessel is ?90 ¡ã C, and the alcohol-based fuel (mixed solution of methanol and dimethyl carbonate) is distilled off; most of the steam distilled out at >90 ¡ã C is dimethyl carbonate, and a small amount of methanol is used as a reaction raw material for recovery. (4) Decompression reaction under reduced pressureStart decompression under reduced pressure, using vacuum distillation, vacuum degree ? -0.08mpa, the temperature rises at a rate of 0.2 ¡ã C per minute,Continue to distill the solution (a mixture of methanol and dimethyl carbonate),Keep the solution evaporated, when the temperature rises to 120 ¡ã C, basically no solvent comes out at this time,The pressure reduction and desolvation can be stopped, and the temperature is lowered; the remaining liquid in the reaction tank is (S)-propylene carbonate. In the crude (S)-propylene carbonate, the (S)-propylene carbonate content is 97percent or more. From the start of the preparation to the preparation of the crude product, the reaction time was 25 hours. (5) Distillation reactionTransfer the remaining liquid after decompression and decompression to the rectification bottle, and turn on the heating and stirring.Vacuuming, ensuring a vacuum degree ? 0.1Mpa, starting the steaming before the fraction, steaming out about 100kg of the former fraction, and then transferring the finished product.The materials in the rectification tank were all distilled off, the rectification was stopped, and (S)-propylene carbonate was collected. The (S)-propylene carbonate has the following quality indicators:1. Appearance: colorless clear liquid;2, SPC chemical purity content (percent): ? 99.8;3, SPC optical purity content (percent): ? 99.4;4. SPC isomer content (percent): ? 0.6;5. Moisture (percent): ? 0.1; The yield of the finished SPC is 97percent; the specific rotation is -2 to -3;

According to the analysis of related databases, (S)-Propane-1,2-diol, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Weifang Huitao Chemical Co., Ltd.; Liu Jianwei; Zhang Quansheng; Wei Lanxing; Hua Xian; (6 pag.)CN109369401; (2019); A;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

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. 4254-15-3,(S)-Propane-1,2-diol, 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.4254-15-3

(1) Feeding800 kg of S-propylene glycol, 1600 kg of dimethyl carbonate and 8 kg of sodium methoxide solution were added to the reaction vessel, and heating and stirring were started.The sodium methoxide solution is a 30percent sodium methoxide/methanol solution;The S-propanediol has a propylene glycol content of 99.5percent, a moisture content of 0.5percent, and a specific rotation of ?16.80-17. (2) Temperature rise reactionFirst stage heating reaction The temperature is raised to 60-65 ¡ã C, at which time a solution (mainly methanol, a small portion of dimethyl carbonate) is distilled off, received in the receiving tank, and the solution is evaporated; Second stage heating reactionThereafter, after about 12 hours, the temperature is raised from 65 ¡ã C to 90 ¡ã C, the solution is kept distilled, and the product is distilled as a by-product alcohol-based fuel (methanol and dimethyl carbonate); Third stage temperature rise reactionHeating was continued, and the temperature was raised from 90 ¡ã C to 115 ¡ã C for 8 hours, and the heating was stopped. (3) Cooling downThe temperature was lowered from 115 ¡ã C to 60 ¡ã C. The temperature in the reaction vessel is ?90 ¡ã C, and the alcohol-based fuel (mixed solution of methanol and dimethyl carbonate) is distilled off; most of the steam distilled out at >90 ¡ã C is dimethyl carbonate, and a small amount of methanol is used as a reaction raw material for recovery. (4) Decompression reaction under reduced pressureStart decompression under reduced pressure, using vacuum distillation, vacuum degree ? -0.08mpa, the temperature rises at a rate of 0.2 ¡ã C per minute,Continue to distill the solution (a mixture of methanol and dimethyl carbonate),Keep the solution evaporated, when the temperature rises to 120 ¡ã C, basically no solvent comes out at this time,The pressure reduction and desolvation can be stopped, and the temperature is lowered; the remaining liquid in the reaction tank is (S)-propylene carbonate. In the crude (S)-propylene carbonate, the (S)-propylene carbonate content is 97percent or more. From the start of the preparation to the preparation of the crude product, the reaction time was 25 hours. (5) Distillation reactionTransfer the remaining liquid after decompression and decompression to the rectification bottle, and turn on the heating and stirring.Vacuuming, ensuring a vacuum degree ? 0.1Mpa, starting the steaming before the fraction, steaming out about 100kg of the former fraction, and then transferring the finished product.The materials in the rectification tank were all distilled off, the rectification was stopped, and (S)-propylene carbonate was collected. The (S)-propylene carbonate has the following quality indicators:1. Appearance: colorless clear liquid;2, SPC chemical purity content (percent): ? 99.8;3, SPC optical purity content (percent): ? 99.4;4. SPC isomer content (percent): ? 0.6;5. Moisture (percent): ? 0.1; The yield of the finished SPC is 97percent; the specific rotation is -2 to -3;

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. (S)-Propane-1,2-diol, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Weifang Huitao Chemical Co., Ltd.; Liu Jianwei; Zhang Quansheng; Wei Lanxing; Hua Xian; (6 pag.)CN109369401; (2019); A;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate