A common heterocyclic compound, the chiral-catalyst compound, name is trans-Cyclohexane-1,2-diamine,cas is 1121-22-8, mainly used in chemical industry, its synthesis route is as follows.,1121-22-8
Into a solution containing 1,6-diisocyanatohexane (2.35 grams, 13.95 mmol; obtained from Sigma-Aldrich Fine Chemicals) and anhydrous hexane (100 mL, obtained from Sigma-Aldrich Fine Chemicals) stirring at room temperature was added diethylene glycol butyl ether (2.27 grams, 14.0 mmol, obtained from Sigma-Aldrich Fine Chemicals), which was previously dried over calcium chloride granules, and dibutyltin dilaurate as catalyst (0.095 grams, 0.15 mmol, obtained from Sigma-Aldrich Fine Chemicals). The mixture was stirred and heated to an internal temperature of about 45 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for the consumption of the diethylene glycol butyl ether starting material. The mixture was cooled to about 15 C. internal temperature; thereafter, to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (0.80 grams, 7.0 mmol; obtained as a racemic mixture of (1R,2R and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous hexane (20 mL). The mixture was stirred for about 30 minutes while warming up to room temperature, and FTIR spectroscopic analysis of a reaction sample indicated no unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). The crystalline product was isolated by vacuum filtration on filter paper, rinsed with hexane, and then dried in air to give 4.82 grams of a white powder (88.8% 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 80 C. and indicated the above structure with the following assigned peaks: 0.90 ppm (multiplet, 3 H integration, -OCH2CH2OCH2CH2OCH2CH2CH2CH3); 1.05-1.95 ppm (broad multiplets, 16 H integration, 4 methylene protons from butyl ether terminus, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 3.0 ppm (narrow multiplet, 5 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O and also tertiary methine proton adjacent to urea group on cyclohexane ring); 3.40-3.70 ppm (multiplets, 8 H integration, NH(CO)OCH2CH2OCH2CH2OCH2CH2CH2CH3); 4.10 ppm (singlet, 2 H integration, NH(CO)OCH2CH2OCH2CH2OCH2CH2CH2CH3); 5.60 ppm and 5.70 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: 58.83%, H: 9.54%, N: 10.83%; found for C: 58.81%, H: 9.58%, N: 12.17%.
As the rapid development of chemical substances, we look forward to future research findings about 1121-22-8
Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare