Author: tianli

Reference of 16369-21-4 ,Some common heterocyclic compound, 16369-21-4, molecular formula is C5H13NO, 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.

A stirred solution of 2-[bis(2-chloroethyl)amino]-3,5-dinitrobenzoic acid (22) (5.00 g, 14.20 mmol) in SOCl2 (50 mL) and DMF (5 drops) was heated under reflux for 3 h, then cooled to room temperature and the excess SOCl2 was removed under reduced pressure. The resulting crude 2- [bis(2-chloroethyl)amino]-3,5-dinitrobenzoyl chloride was dissolved in THF (40 mL) and slowly added to a stirred solution of 2-(propylamino)ethanol (4.60 g, 44.63 mmol) in THF (40 mL) at -10 C. The mixture was stirred for 20 min at -10 0C, then treated with aqueous HCl (0.5 M, 40 mL) to pH ~ 3 before being extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with CH2Cl2/MeOH (99:1) to give 2-[bis(2-chloroethyl) amino]-iV-(2-hydroxyethyl)-3,5-dinitro-iJ-propylbenzamide (26) (3.73 g, 60%) as a yellow oil. 1HNMR [(CDj)2SO] (mixture of rotamers) delta 8.71, 8.68 (2dJ = 2.8 Hz, IH), 8.38, 8.24 (2dJ = 2.8 Hz, IH), 4.84, 4.80 (2tJ = 5.2 Hz, IH), 3.72-3.65 (m, 5H), 3.63-3.42 (m, 4H), 3.39-3.31 (m, 2H),3.24-3.12 (m, 2H), 1.66, 1.55 (2m, 2H), 0.94, 0.73 (2tJ = 7.4 Hz, 3H). HRMS(ESI) calcd for C16H23 Cl2N4O6 [M+H]+ m/z 437.0989: found 437.0993.

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. 16369-21-4, 2-(Propylamino)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; PATTERSON, Adam, Vorn; SMAILL, Jeffrey, Bruce; DENNY, William, Alexander; WILSON, William, Robert; SYDDALL, Sophie; ASHOORZADEH, Amir; WO2010/44685; (2010); A1;,
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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. 5391-88-8, name is 1-(4-Bromophenyl)ethanol, molecular formula is C8H9BrO, The 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. Safety of 1-(4-Bromophenyl)ethanol

General procedure: Catalyst (2 mol%), aryl halide (1 equiv.) and Na2CO3 (1.1 equiv.) were stirred in H2O (5 mL) taken in the round bottom flask. The aryl boronic acid (1.1 equiv.) was added to the stirring solution. Stirring was continued for required time at 45 C. After the requisite time, the reaction mixture was diluted with water and the product was extracted with ethyl acetate. The ethyl acetate extract was passed through celite bed and then analyzed by GC. Authentic samples of both reactant and product were used to verify the retention time and to confirm the product formation. The ethyl acetate extract was concentrated and chromatographed on a silica gel column using hexane and ethylacetate as eluent to afford coupled product. The products are characterized by NMR, GC MS and UPLC analyses.

With the rapid development of chemical substances, we look forward to future research findings about 5391-88-8.

Reference:
Article; Ganesamoorthy; Shanmugasundaram; Karvembu; Journal of Molecular Catalysis A: Chemical; vol. 371; (2013); p. 118 – 124;,
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Related Products of 612-16-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.612-16-8, name is (2-Methoxyphenyl)methanol, molecular formula is C8H10O2, molecular weight is 138.16, as common compound, the synthetic route is as follows.

Add 2-methylquinoline (1mmol), 2-methoxybenzyl alcohol (2.5mmol), TEMPO (0.1mmol), Fe (NO3) 3.9H2O (0.1mmol) andt-BuOK (2mmol) was sequentially added to a flask containing 2mL of THF,The air in the flask was replaced with oxygen, and the reaction was stirred at 50 C.The reaction process was monitored by thin layer chromatography. After the reaction was completed, it was quenched with water (10 mL).The reaction product was extracted with ethyl acetate (3 × 20 mL), washed with saturated brine (20 mL), dried over anhydrous Na2SO4, filtered, and the resulting filtrate was concentrated, and passed through silica gel column chromatography (200-300 mesh, the developing solvent was petroleum ether). (20: 1 mixed solution with ethyl acetate in volume ratio) yielded 215.0 mg of product with a yield of 82%.

Statistics shows that 612-16-8 is playing an increasingly important role. we look forward to future research findings about (2-Methoxyphenyl)methanol.

Reference:
Patent; Hebei University of Science and Technology; Zhang Zhiguang; Zhang Yong; Li Ling; Dai Siwei; Li Xingxi; (18 pag.)CN110804015; (2020); A;,
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Application of 3637-61-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.3637-61-4, name is Cyclopentanemethanol, molecular formula is C6H12O, molecular weight is 100.16, as common compound, the synthetic route is as follows.

REFERENCE EXAMPLE 13 STR43 Methanesulfonyl chloride (1.52 g) was added dropwise to a solution of 1.11 g of cyclopentanemethanol and 1.50 g of triethylamine in 30 ml of dichloromethane with cooling on an ice bath over 5 minutes. The reaction mixture was stirred at room temperature for 30 minutes and then washed in sequence with three portions of water and one portion of saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.06 g of cyclopentanemethyl methanesulfonate. NMR (CDCl3) delta: 1.1~1.9 (8H), 2.1~2.5 (1H, m), 2.02 (3H, s), 4.13 (2H, d, J=7 Hz), MS: m/z 178 (M+) STR44

The chemical industry reduces the impact on the environment during synthesis 3637-61-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4987132; (1991); A;,
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Synthetic Route of 20712-12-3, 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. 20712-12-3, name is (2-Amino-5-bromophenyl)methanol. A new synthetic method of this compound is introduced below.

A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20712-12-3, (2-Amino-5-bromophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Bifulco, JR., Neil; DiPietro, Lucian V.; Miduturu, Chandrasekhar V.; US2015/197519; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2516-33-8, Cyclopropylmethanol, 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, Safety of Cyclopropylmethanol, blongs to alcohols-buliding-blocks compound. Safety of Cyclopropylmethanol

To a 2 L flask was charged with cyclopropanemethanol (8A) (18 g, 250 mmol, 1 equiv), TEMPO (78 mg, 0.5 mmol) and CH2Cl2 (250 mL). The solution was cooled to 0 C, and a solution of KBr (2.99 g, 25 mmol, 0.1 equiv), NaHCO3 (52.5 g, 625 mmol, 2.5 equiv), and 10-13% NaOCl (150 mL, 313 mmol, 1.25 equiv) in H2O (80 mL) was then slowly added. After the resulting mixture was had been stirring at 0 C for 45 min, the two layers were separated. The aqueous layer was back extracted with CH2Cl2 (2 x 250 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resulting residue was purified via shortpath distillation head under N2 (95-100 C) to give the corresponding aldehyde 8B (11. 02 g, 73%) as a colorless liquid.

The synthetic route of 2516-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Trost, Barry M.; Nguyen, Hien M.; Koradin, Christopher; Tetrahedron Letters; vol. 52; 17; (2011); p. 2033 – 2036;,
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Electric Literature of 25125-21-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.25125-21-7, name is 1-Hydroxymethyl-3-cyclopentene, molecular formula is C6H10O, molecular weight is 98.143, as common compound, the synthetic route is as follows.

1-a (Cyclopent-3-en-1-yl)methyl toluenesulfonate A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). Yield(%): 83.2 1 H NMR(CDCl3): delta2.11(2H,m), 2.42(3H,s), 2.49(3H,m), 3.82(2H,d), 5.67(2H,s), 7.40(2H,d), 7.65(2H,d).

The chemical industry reduces the impact on the environment during synthesis 25125-21-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samjin Pharmaceutical Co., Ltd; US5922727; (1999); A;,
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Application of 29683-23-6 ,Some common heterocyclic compound, 29683-23-6, molecular formula is C5H10OS, 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.

INTERMEDIATE 17(2-Oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazol- 1 -yPacetic acidStep A. fert-Butyl 2-oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazole- 1 – carboxylateDiethyl azodicarboxylate (446 mg, 2.56 mmol) was added to a solution otert- butyl 2-oxo-2,3-dihydro-lH-benzimidazole-l -carboxylate (J Org. Chem., 1995, 60, 1565-1582) (500 mg, 2.13 mmol), triphenylphosphine (672 mg, 2.56 mmol), and tetrahydro-2H-thiopyran-4- ol (Chem. Comm., 2002, 10, 1070-1071) (303 mg, 2.56 mmol) in TetaF (10 mL). After 20 h, the reaction was concentrated in vacuo and the crude product purified by silica gel column chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 95:5, to give the title compound. MS: m/z = 335 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29683-23-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/130512; (2008); A1;,
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Electric Literature of 111-90-0, 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. 111-90-0, name is Diethylene Glycol Monoethyl Ether. A new synthetic method of this compound is introduced below.

[00121] Charge copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,3-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mmol), di(ethylene glycol) ethyl ether (FW 134.71, 14.06 grams, 104.40 mmol) and 100 milliliters of dry xylene in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflex temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then the reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 180C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product was yielded 5.20 grams (67%). The product IR, and C NMR analysis shows the formation of aryl ether product. IR: neat (cm” FontWeight=”Bold” FontSize=”10″ ): 687, 763, 843, 995, 1058, 1 116, 1 157, 1 185, 1264, 1289, 1333, 1351, 1418, 1452, 1492, 1590, 2874. 13C NM (CDC13): 149.22, 121.87, 1 15.18, 70.84, 70.65, 69.83, 68.90, 66.5, 15.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-90-0, Diethylene Glycol Monoethyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; PATIL, Abhimanyu O.; BODIGE, Satish; WO2015/60984; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 96-35-5, Methyl 2-hydroxyacetate, 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, Product Details of 96-35-5, blongs to alcohols-buliding-blocks compound. Product Details of 96-35-5

4-(3-(3-Fluoro-4-hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 1e (100 mg, 0.24 mmol) was placed in a reaction flask, followed by addition of methyl glycolate (42 mg, 0.47 mmol), triphenylphosphine (93 mg, 0.35 mmol), 5 mL of dichloromethane, and diisopropyl azodicarboxylate (72 mg, 0.35 mmol), successively. The reaction solution was stirred for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system A to obtain the title compound methyl 2-(4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluorophenoxy)acetate 31a (104 mg, yield 89.7%) as a white solid. MS m/z (ESI): 496.2 [M+1]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96-35-5, Methyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Medicine Co., Ltd.; Lu, Hejun; Sun, Piaoyang; Fei, Hongbo; Jiang, Hongjian; Wang, Haowei; Dong, Qing; US2015/225381; (2015); A1;,
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