With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine
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
To a solution containing 1,6-diisocyanatohexane (5.04 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 milliliters) stirring at room temperature was added 1,4-butanediol vinyl ether (3.48 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.19 grams, 0.3 mmol; obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 65 C. for 25 minutes. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the 1,4-butanediol vinyl ether reactant, 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 15 C. internal temperature after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.71 grams, 15 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous tetrahydrofuran (10 milliliters). The mixture was stirred for about 60 minutes while warming up to room temperature, and thickened to form a gelatinous slurry. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give a semi-solid product, which was subsequently stirred in hexane to ensure full precipitation. The solid product was filtered and dried in air to give 8.17 grams of a white powder (79 percent 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: 1.05-1.90 ppm (several multiplets, 16 H integration, 4 methylene protons from 1,4-butanediol vinyl ether portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O-); 3.2 ppm (broad singlet, 1 H integration, tertiary methane proton adjacent to urea group on cyclohexane ring); 3.70 ppm (multiplet, 2 H integration, NH(CO)O(CH2)4-O-C(Hc)C(Ha)(Hb)); 3.96 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 3.98 ppm (multiplet, 2 H integration, NH(CO)OCH2CH2CH2CH2-O-C(Hc)C(Ha)(Hb)); 4.20 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 5.60 ppm and 5.72 ppm (broad singlets, each 1 H integration, urea NH protons); 6.48 ppm (doublet of doublets, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 6.82 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 59.80%, H: 9.15%, N: 12.31%; found for C: 59.36%, H: 9.53%, N: 12.58%.
With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine
Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
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