Day: November 19, 2020

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

(1) Synthesis of N,N’-di-p-toluenesulfonyl-1,1′-binaphthyl-2,2′-diamine Under nitrogen atmosphere, to a solution in which 1,1′-binaphthyl-2,2′-diamine (0.5 mmol) was dissolved in pyridine (1 mL) was added p-toluenesulfonyl chloride (1.1 mmol) at room temperature, and the mixture was reacted for 5 to 12 hours with stirring. After completion of the reaction, the resulting red suspension was diluted with ethyl acetate, and back-extracted with 1N hydrochloric acid to remove pyridine. The resulting organic layer was dried with sodium sulfate to remove the solvent, and the residue was purified by column chromatography to obtain an objective substance as a pale yellow to white solid in more than 95% yield.

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Patent; Terada, Masahiro; Uraguchi, Daisuke; Sorimachi, Keiichi; Shimizu, Hideo; US2007/142639; (2007); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

1,3-Dimesityl-1H-imidazol-3-ium chloride, cas is 141556-45-8, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,141556-45-8

In a Schlenk flask under argon, to a THF suspension (20 mL) of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (1 g, 2.93 mmol), solid potassium tert-butoxide (0.35 g, 3.12 mmol) was added in a single portion. The mixture was stirred for 45 min at room temperature, and volatiles were removed under vacuum. After addition of THF (20 mL) and stirring for 5 min, the reaction mixture was filtered under argon, and carbon tetrabromide (2.42 g, 5.86 mmol) in THF (10 mL) was added dropwise to solution, over a period of ca. 30 min. The resulting brown solution was stirred for 4 h. Subsequent removal of volatiles in vacuo gave a dark brown residue that was extracted into toluene (10 mL) and then a solution of HCl in dioxane (4 mol/L) was added, and the resulting white precipitate was collected. Yield 351 mg (29%). 1H NMR (500 MHz, DMSO-d6): delta 2.13 (s, 12H, o-CH3), 2.39 (s, 6H, p-CH3), 7.27 (s, 4H, Ar-H), 10.13 (s, 1H, HNCN); 1H NMR (500 MHz, CDCl3): delta 2.20 (s, 6H, p-CH3), 2.54 (s, 12H, o-CH3), 6.82 (s, 4H, Ar-H), 10.16 (s, 1H, HNCN); 13C NMR (125 MHz, DMSO-d6): delta 16.9, 20.7, 113.1, 129.3, 129.6, 135.1, 140.5, 141.7; Elemental analysis calcd. for C21H23Br2ClN2: C 50.58, H 4.65, N 5.62; found C 50.55, H 4.59, N 5.67; ESI-MS (C21H23Br2Cl1N2) (m/z): 497.4 [M]+.

With the rapid development of chemical substances, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride

Reference£º
Article; Amini, Mojtaba; Bagherzadeh, Mojtaba; Rostamnia, Sadegh; Chinese Chemical Letters; vol. 24; 5; (2013); p. 433 – 436;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is trans-Cyclohexane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

General procedure: Aldehyde (2.2 mmol, salicylaldehyde or 4-methoxysalicylaldehyde, 4-diethylamino-2-hydroxy benzaldehyde or 2,4-dihydroxybenzaldehyde) was dissolved in ethanol (30 ml) and stirred at room temperature. To this solution, either ethylene diamine (1 mmol) or trans-1,2-diaminocyclohexane (1 mmol) was added drop-wise under stirring. The immediate appearance of yellow colour indicates the formation of Schiff bases. The solution was allowed to stir for another 6 h at room temperature that produced yellow to light yellow coloured precipitates. The formed precipitate was filtered off, washed with ethanol and dried under vacuum.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Article; Hariharan; Anthony, Savarimuthu Philip; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 136; PC; (2015); p. 1658 – 1665;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 250285-32-6, its synthesis route is as follows.,250285-32-6

A vial was charged with [Au(SMe2)Cl] (53mg, 190mumol, 1.06 equiv.), IPr.HCl (76mg, 179mumol, 1 equiv.) and KOtBu (31mg, 277mumol, 1.5 equiv.) in THF (0.5mL), under air. The mixture was stirred for 2h at room temperature. KOtBu (62mg, 553mumol, 3 equiv.) was then added followed by toluene (0.5mL). After 3h at room temperature, the crude mixture was then filtered through Celite and washed with additional THF. Water (0.1mL) was added to the solution and the solution was stirred for an additional 15min. THF was then removed under vacuum. More water was added to the white, cloudy suspension and the product was vigorously stirred for a few minutes. It was left to settle for 10min, collected using a Buchner funnel and washed with hexane. It was then dried under vacuum for several days to produce a white microcrystalline solid.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Article; Nahra, Fady; Patrick, Scott R.; Collado, Alba; Nolan, Steven P.; Polyhedron; vol. 84; (2014); p. 59 – 62;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO33,mainly used in chemical industry, its synthesis route is as follows.,23190-16-1

To a 5 L round bottom flask equipped with an overhead stirrer, thermocouple and distillation head, was charged 550 g (2.579 mol) of (1R, 2S)-diphenyl-2-aminoethanol, 457 g (3.868 mol, 1.5eq) of diethylcarbonate, 18 g (0.258 mol, O.leq) of NaOEt in 100 mL of EtOH and 3.5 L of toluene. The reaction was heated until an internal temperature of 90C was reached and EtOH distillation began. The reaction was refluxed until an internal temperature of 110C was reached (7 hours). For every 500 mL of solvent that was removed via the distillation head, 500 mL of toluene was added back to the reaction. A total of about 1.6 L of solvent was removed. The reaction was allowed to cool to room temperature and then filtered on a 3 L coarse fritted funnel with 2 psig N2. Nitrogen was blown over the cake overnight to give 580 g (94% yield) of the title compound: ‘H NMR (DMSO) No. 7.090-6.985 (m, 6H), 6.930-6.877 (m, 4H), 5.900 (d, 1H, J = 8.301), 5.206 (d, 1H, J = 8.301).

With the synthetic route has been constantly updated, we look forward to future research findings about (1R,2S)-2-Amino-1,2-diphenylethanol,belong chiral-catalyst compound

Reference£º
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/102390; (2005); A2;,
Chiral Catalysts
Chiral catalysts – SlideShare

[1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,4488-22-6

7-1A (28.5 g, 100 mmol) was dissolved in acetonitrile (MeCN), and 10 ml of hydrochloric acid was slowly added thereto, followed by stirring at room temperature for 3 hours. After the reaction was completed by adding water, the resulting solid was filtered, washed with an aqueous solution of potassium carbonate and dried to obtain the compound of Formula 7-1B (25 g, yield 90%).

4488-22-6 is used more and more widely, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Patent; LG Chemical Co., Ltd.; Sin, Chang Hwan; Kim, Kong Gyeom; Cheon, Min Sung; Kwon, Hyuk Jun; Kim, Dong Heon; (50 pag.)KR101656560; (2016); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare

1,4,7,10,13-Pentaoxacyclopentadecane, cas is 33100-27-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,33100-27-5

Sodium hydride (60percent dispersion in mineral oil, 0.14 g) was added portionwise to a stirred solution of a portion (0.87 g) of the 3-hydroxypyrrolidine so obtained and 1,4,7,10,13-pentaoxacyclopentadecane (hereinafter 15-crown-5, 0.05 g) in DMF (10 ml). The mixture was stirred at ambient temperature for 15 minutes. A solution of methyl 4-toluenesulphonate (0-56 g) in THF (2 ml) was added dropwise and the mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between diethyl ether and water. The organic phase was dried (Na2 SO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluent. There was thus obtained 1-benzyl-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.82 g, 90percent).

33100-27-5 is used more and more widely, we look forward to future research findings about 1,4,7,10,13-Pentaoxacyclopentadecane

Reference£º
Patent; Zeneca Limited; Zeneca Pharma S.A.; US5420298; (1995); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22795-99-9,(S)-(1-Ethylpyrrolidin-2-yl)methanamine,as a common compound, the synthetic route is as follows.

In a 100 mL eggplant bottle, 1.22 g of benzaldehyde, 30 mL of anhydrous ethanol,(S) -1-ethyl-2-aminomethyltetrahydropyrroline, and the mixture was heated under reflux for 24 hours.Adding 0.76 g of sodium borohydride, stirring for 3 hours, cooling to room temperature, pouring into water, dichloromethane extraction organic phase, anhydrous magnesium sulfate drying, extraction solvent to light yellow viscous liquid. Add 30 mL of absolute ethanol,0.6 g of paraformaldehyde, 3.30 g of 2,4-dicumylphenol, and heated under reflux for 12 hours.The crude product was chromatographed on silica gel to give a pale brown liquid L3 (3.41 g, 60.9percent)., 22795-99-9

As the paragraph descriping shows that 22795-99-9 is playing an increasingly important role.

Reference£º
Patent; East China University of Science and Technology; Ma, HaiYan; Wang, haobing; (35 pag.)CN103787943; (2016); B;,
Chiral Catalysts
Chiral catalysts – SlideShare

trans-Cyclohexane-1,2-diamine, cas is 1121-22-8, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,1121-22-8

Into a solution containing 1,6-diisocyanatohexane (4.04 grams, 24.0 mmol; obtained from Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 mL, Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) stirring at room temperature was added 2-ethylhexanol (3.13 grams, 24.0 mmol, obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.38 grams, 0.6 mmol, obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 70 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for the consumption of 2-ethylhexanol starting material, indicated by the disappearance of the -CH2OH multiplet, which appears at 3.5 ppm as a shoulder peak on the downfield end of the intermediate isocyanate product whose signal is located at 3.35-3.40 ppm. The mixture was cooled to about 5 C. internal temperature; thereafter, to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.37 grams, 12 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous tetrahydrofuran (10 mL). The mixture was stirred for about 30 minutes while warming up to room temperature, and thickened to form a gelatinous slurry. FTIR spectroscopic analysis of a reaction sample showed very little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Residual isocyanate was quenched by addition of 5 mL of methanol. A crystalline product was isolated from the slurry by first adding methylene chloride (40 mL) followed with stirring for approximately 20 minutes to ensure full precipitation out of the gel slurry. The solid was filtered by suction on a paper filter, rinsed with methylene chloride (about 10 mL), and then dried in air to give 7.36 grams of off-white solid (86% yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 MHz) at high temperature (60 C.) and indicated the above structure, with the following assigned peaks: 0.90 ppm (multiplet, 6 H integration, -OCH2CH(CH2CH3)CH2CH2CH2CH3); 1.0-1.95 ppm (broad multiplets, 20 H integration, 8 methylene protons from 2-ethylhexanol portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (narrow multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O); 3.20 ppm (broad singlet, 1 H integration, tertiary methine proton adjacent to urea group on cyclohexane ring); 3.90 ppm (doublet, 2 H integration, OCH2CH(CH2CH3)CH2CH2CH2CH3); 5.65 ppm and 5.75 ppm (each a broad singlet, 1 H integration, urea NH protons); 6.75 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 64.19%, H: 10.49%, N: 11.82%; found for C: 61.70%, H: 9.86%, N: 14.91%.

1121-22-8 is used more and more widely, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,D-Phenylalanine,673-06-3,Molecular formula: C9H11NO2,mainly used in chemical industry, its synthesis route is as follows.,673-06-3

(R)-phenylalanine (4.2 g, 25 mmol) was sequentially added to the dry reaction flask.Water (30mL),1,4-dioxane(30mL) andSodium bicarbonate (5.1 g, 61 mmol),After the mixture was stirred for 10 minutes,Add (Boc) 2O (10.1g,45.8mmol),The resulting mixture was stirred at room temperature for 24 h.After the reaction, the solvent was distilled off under reduced pressure, the resulting residue was washed with water (20mL) and EtOAc (100mL) was diluted with 1M HCl and then adjusted to pH 6-7, was allowed to stand, and the organic layer was washed with water and saturated brine, dried over anhydrous sulfate Dry the sodium, filter, and distill off the solvent under reduced pressure.The title compound was obtained as a colorless oil (6.0 g, 91%)

With the synthetic route has been constantly updated, we look forward to future research findings about D-Phenylalanine,belong chiral-catalyst compound

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ¡¤geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
Chiral Catalysts
Chiral catalysts – SlideShare