Month: September 2021

Application of 612-16-8 , The common heterocyclic compound, 612-16-8, name is (2-Methoxyphenyl)methanol, molecular formula is C8H10O2, 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.

General procedure: Reactions were performed in a magnetically stirred round bottomed flask fitted with acondenser and placed in a temperature controlled oil bath. 1,2-Diamine (2 mmol)was added to alcohol (3 mmol) and the reaction mixture was allowed to stir at 135C in an open (air) atmosphere. After disappearance of the diamine (reaction was monitored by TLC)or after the appropriate time, the reaction mixture was cooled to roomtemperature. The crude residue was further purified by column chromatography using silica gel (100-200 mesh) to afford pure products. All the products wereidentified on the basis of NMR and mass spectral data

The synthetic route of 612-16-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Marri, Mahender Reddy; Peraka, Swamy; Macharla, Arun Kumar; Mameda, Naresh; Kodumuri, Srujana; Nama, Narender; Tetrahedron Letters; vol. 55; 48; (2014); p. 6520 – 6525;,
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Electric Literature of 4139-61-1, 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. 4139-61-1, name is 6-Bromo-4-hydroxycoumarin. A new synthetic method of this compound is introduced below.

Step one: the 6 – bromo -4 – hydroxy coumarin (1 mmol) with triethylamine (1.5 mmol) dissolved in 10 ml dichloromethane after, cold water bath cooling, trifluoromethyl sulfonic acid anhydride (1.5 mmol) is added slowly dropping in the reaction system, the reaction 3 hours later, and steaming and to remove the solvent, after concentrating column separation (petroleum ether and ethyl acetate to the volume proportion 4:1) to obtain 6 – bromo -4 – trifluoromethanesulfonic acid ester – coumarin.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4139-61-1, its application will become more common.

Reference:
Patent; Henan University of Technology; Wang Hongyan; Wei Xuning; Liu Yu; Guo Tao; Lin Xiangbin; Kong Linghui; (33 pag.)CN107629050; (2018); A;,
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Synthetic Route of 60666-70-8, 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. 60666-70-8, name is (2-Bromo-5-chlorophenyl)methanol, molecular formula is C7H6BrClO, 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.

Step 1. ((2-Bromo-5-chlorobenzyl)oxy)(tert-butyl)dimethylsilane. Triethylamine (0.30 mL, 2.15 mmol), DMAP (97 mg, 0.79 mmol) and tert-butyldimethylsilyl chloride (TBSCl; 698 mg, 4.63 mmol) were added to a solution of (2-bromo-5-chlorophenyl)methanol (500 mg, 2.26 mmol) in CH2Cl2 (11.3 mL) at room temperature. After stirring overnight, the reaction mixture was partitioned between saturated aqueous sodium bicarbonate (50 mL) and CH2Cl2 (200 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2*100 mL). The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo.

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 60666-70-8, (2-Bromo-5-chlorophenyl)methanol.

Reference:
Patent; Allergan, Inc.; Ngo, Vinh X.; Old, David W.; Burk, Robert M.; (55 pag.)US9540357; (2017); B1;,
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Reference of 7589-27-7, 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 compound 7589-27-7, name is 2-(4-Fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(4-fluorophenyl)ethyl alcohol (13.4 mL, 107 mmol) in dry toluene (150 mL) at 0C was added phosphorous tribromide (21.1 mL, 224 mmol). The resulting mixture was stirred at ambient temperature for 5 days and then recooled to 0C and crushed ice (200 g) added. The aqueous layer was extracted with ether (2 x 120 mL) and the combined organic extracts were then washed with saturated aqueous sodium bicarbonate solution (2 x 30 mL), dried (MgSO4) and concentrated in vacuum. Distillation afforded 2-(4-fluorophenyl)ethyl bromide as a colorless oil (14.08g, 31%); b.p. 103C (at) 12 mm Hg.

According to the analysis of related databases, 7589-27-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharmaceuticals, Inc.; Hoechst Marion Roussel Deutschland GmbH; EP1734037; (2006); A2;,
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Electric Literature of 454-91-1, 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.454-91-1, name is 1-[3-(Trifluoromethyl)phenyl]ethanol, molecular formula is C9H9F3O, molecular weight is 190.16, as common compound, the synthetic route is as follows.

Example 90 1-[3-(Trifluoromethyl)phenyl]ethyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (89 mg) was added to toluene/triethylamine = 10/1 (9 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (120 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-trifluoromethyl-alpha-methylbenzyl alcohol (70 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (80 mg, yield 48%). 1H-NMR (CDCl3, 400 MHz): 8.75 (1H, s), 8.07 (1H, s), 7.14 – 7.63 (8H, m), 6.95 (1H, s), 6.79 (1H, d, J = 8.8 Hz), 5.93 (1H, q, J = 6.6 Hz), 4.15 (3H, s), 4.09 (3H, s), 1.61 (3H, d, J = 6.6 Hz) Mass spectrometry value (ESI-MS, m/z): 514 (M++1)

Statistics shows that 454-91-1 is playing an increasingly important role. we look forward to future research findings about 1-[3-(Trifluoromethyl)phenyl]ethanol.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1243582; (2002); 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, 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. Computed Properties of C9H7F6NO

A solution of 2-(4-aminophenyl)- 1,1, 1,3,3, 3-hexafluoropropan-2-ol (0.88 g, 3.4 mmol), 2-acetamido-4-methylthiazole-5-sulfonyl chloride (0.79 g, 3.1 mmol) in acetone (15 mL) and 2,6-lutidine (0.73 mL, 6.2 mmol) was warmed to 60°C for 18 h. The reaction was judged complete by analytical HPLC (starting materials consumed). The solvent was removed in vacuo, and the crude residue was diluted with EtOAc and aq 1M HC1. The layers were separated, and the organic layer was washed with 1M HC1, sat aq NaHC03, brine, dried (MgS04), and concentrated to give a solid.Trituration with warm Et20/hexanes afforded N-(5-(N-(4-(l,l,l,3,3,3-hexafluoro-2- hydroxypropan-2-yl)phenyl)sulfamoyl)-4-methylthiazol-2-yl)acetamide (1.2 g, 86percent yield) as a light tan solid, >95percent pure as judged by analytical HPLC. A small amount of this was further purified by reverse-phase preparative HPLC to >99percent purity to give a colorless solid. 1H NMR (DMSO-J6, 400MHz) delta 12.5 (s, 1H); 10.8 (s, 1H); 8.6 (s, 1H); 7.60 (d, 2H); 7.25 (d, 2H); 2.30 (s, 3H); 2.15 (s, 3H); 13C NMR (DMSO-J6, 100MHz) delta 170.0, 159.6, 153.0, 139.4, 128.4, 126.8, 124.8, 121.9, 121.7, 120.3, 22.8, 16.3; 19F NMR (DMSO-J6, 376MHz) delta -74.1; HRMS (ESI-orbitrap) Calcd for C15Hi4F6N304S2, 478.0330; Found, 478.0319.

With the rapid development of chemical substances, we look forward to future research findings about 722-92-9.

Reference:
Patent; GRIFFIN, Patrick R.; ROUSH, William R.; KUMAR, Naresh; NUHANT, Philippe; BURRIS, Thomas; SOLT, Laura; WO2011/115892; (2011); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 5456-63-3, trans-2-Aminocyclohexanol hydrochloride, 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, HPLC of Formula: C6H14ClNO, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C6H14ClNO

A mixture of 5-chloro-6-ethyl-3-{3-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino}pyrazine-2-carboxamide (11, 150 mg,0.307 mmol), rac-(1R,2R)-2-aminocyclohexan-1-ol monohydrochloride(140 mg, 0.921 mmol), DIPEA (164 muL, 0.921 mmol) and NMP (3 mL) was irradiated with microwaves at 190 C for 60 min. After the mixture was cooled, water was added, and the resulting precipitate was filtered. The obtained solid was purified by silica gel column chromatography(CHCl3/MeOH=84:16) to give 12b (61 mg, 35%) as a brown solid. 1HNMR (DMSO-d6): delta 1.05-1.32 (4H, m), 1.20 (3H, t, J=7.5 Hz),1.45-1.59 (2H, m), 1.59-1.74 (2H, m), 1.74-1.86 (2H, m), 1.86-2.04(2H, m), 2.14 (3H, s), 2.18-2.67 (13H, m), 3.20-3.41 (2H, m),3.48-3.61 (1H, m), 3.73-3.87 (1H, m), 3.82 (3H, s), 4.64 (1H, d,J=5.0 Hz), 6.56 (1H, d, J=7.5 Hz), 6.79 (1H, d, J=8.5 Hz),7.10-7.23 (3H, m), 7.48 (1H, d, J=2.5 Hz), 11.03 (1H, s); MS (ESI) m/z [M+H]+ 567; HRMS (ESI) m/z Calcd for C30H47N8O3 [M+H]+:567.3766, Found: 567.3768.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5456-63-3, trans-2-Aminocyclohexanol hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Iikubo, Kazuhiko; Kurosawa, Kazuo; Matsuya, Takahiro; Kondoh, Yutaka; Kamikawa, Akio; Moritomo, Ayako; Iwai, Yoshinori; Tomiyama, Hiroshi; Shimada, Itsuro; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1683 – 1692;,
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Synthetic Route of 505-10-2, 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. 505-10-2, name is 3-(Methylthio)propan-1-ol, molecular formula is C4H10OS, 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.

The 3-mesylpropanol used as a starting material was prepared as follows: 3-Chloroperoxybenzoic acid (25 g) was added in portions to a solution of 3-methylthiopropanol (5 ml) in methylene chloride (100 ml) while maintaining the reaction temperature at 25 C. The mixture was stirred at ambient temperature for 1 hour. The mixture was filtered and the filtrate was diluted with an aqueous solution of sodium sulphite (6.5 g) in water (200 ml). The organic layer was separated and evaporated. The white residue was triturated under acetone and the resultant solution was evaporated to give a solid which was dissolved in methylene chloride. Aluminum oxide (90 mesh) was added and the mixture was allowed to stand for 15 minutes. The mixture was filtered and the filtrate was evaporated to give 3-mesylpropanol as a colourless oil (4.46 g); NMR Spectrum: (CDCl3) 1.9-2.1 (br s, 1H), 2.15 (m, 2H), 2.95 (s, 3H), 3.2 (t, 2H), 3.85 (t, 2H).

According to the analysis of related databases, 505-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hennequin, Laurent Francois Andre; Crawley, Graham Charles; McKerrecher, Darren; Ple, Patrick; Poyser, Jeffrey Philip; Lambert, Christine Marie Paul; US2003/225111; (2003); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 765-04-8, 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.765-04-8, name is Undecane-1,11-diol, molecular formula is C11H24O2, molecular weight is 188.3071, as common compound, the synthetic route is as follows.

In a four-necked flask (volume of 1 L) equipped with stirring blades, a thermometer, a dropping funnel and a condenser tube, 300 mL of tetrahydrofuran, 18.8 g (0.10 mol) of undecane-1,1l-diol and 14.4 mg of p-methoxyphenol were charged and dissolved. Subsequently, 9.96 g (0.05 mol) of 2-(2-isocyanatoethoxy)ethyl methacrylate was weighed in a beaker and 150 mL of tetrahydrofuran was added, followed by sufficient stirring and further liquid transfer to the dropping funnel. The four-necked flask was immersed in an oil bath heated to 75 C., and 2-(2-isocyanatoethoxy)ethyl methacrylate was added dropwise so as not to cause boiling of tetrahydrofuran. After completion of the dropwise addition, the reaction was continued for 24 hours while maintaining the temperature of the oil bath, leading to aging. After completion of the aging, the four-necked flask was removed from the oil bath and the reaction product was returned to room temperature, and then HPLC and FT-IR measurements were performed. In that case, a sample obtained by collecting a very small amount of the reaction product using a pipette and removing a solvent using evaporator was used. Analysis conditions of the HPLC measurement are as follows: a column of ZORBAX-ODS, acetonitrile/distilled water of 7/3, a flow rate of 0.5 mL/min, a multi-scanning UV detector, an RI detector and an MS detector. The FT-IR measurement was performed by an ATR method. As a result of the HPLC measurement, peaks of undecane-1,11-diol and 2-(2-isocyanatoethoxy)ethyl methacrylate as raw materials disappeared, and new peak of 2-(2-((((11-hydroxyundecyl)oxy)carbonyl)amino)ethoxy)ethyl methacrylate (molecular weight of 387.52) was confirmed. As a result of the FT-IR measurement, the disappearance of the isocyanate absorption at 2,280 to 2,250 cm-1 and a decrease in intensity of the hydroxy group absorption at around 3,300 cm-1 were confirmed, and the absorption attributed to a urethane group was newly confirmed at 1,250 cm-1. Subsequently, to a tetrahydrofuran solution containing 28.8 g (74.2 mmol) of the precursor compound synthesized by the above-mentioned operation, 15.2 g (74.2 mmol) of (3-isocyanatopropyl)trimethoxysilane was added dropwise while stirring so as not to cause boiling of tetrahydrofuran. In the same manner as in the first stage, a reaction was performed by immersing in an oil bath heated to 75 C. After completion of the dropwise addition, the reaction was continued for 24 hours, leading to aging. After completion of the aging, HPLC and FT-IR measurements were performed. As a result of the HPLC measurement, peaks of 2-(2-((((11-hydroxyundecyl)oxy)carbonyl)amino)ethoxy)ethyl methacrylate and (3-isocyanatopropyl)trimethoxysilane as raw materials disappeared, and new peak of 3,3-dimethoxy-8,22-dioxo-2,9,21,26-tetraoxa-7,23-diaza-3-silaoctacosan-28-ylmethacrylate (molecular weight of 592.80) was confirmed. As a result of the FT-IR measurement, the disappearance of the hydroxy group absorption at around 3,300 cm-1 was confirmed. The chemical structure of the compound synthesized in the present Synthesis Example is mentioned below.

Statistics shows that 765-04-8 is playing an increasingly important role. we look forward to future research findings about Undecane-1,11-diol.

Reference:
Patent; KABUSHIKI KAISHA SHOFU; FUCHIGAMI, Kiyomi; YAMAMOTO, Kenzo; KITADA, Naoya; SHINNO, Kazuya; US2019/300552; (2019); A1;,
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