Formic Acid → N,N'-Dicyclohexylurea

Participants

Reaction Steps

To a solution of formic acid (0.026 g, 0.556 mmol) in chloroform (1.5 mL) was added dropwise dicyclohexylcarbodiimide (DCC) (0.114 g, 0.56 mmol) in chloroform (1.5 mL) at 0° C. After 5 min the above solution was added to the compound 9 (0.10 g, 0.28 mmol) in pyridine (2 mL). The mixture was then stirred for 1 hours at room temperature. Evaporation of solvent was followed by addition of ether gave dicyclohexylurea which was removed via filtration and the solid was washed with ether. The combined filtrate was concentrated and purified by flash column chromatography to give the product 11, (EM 347) (0.075 g, 70%); 1H NMR (CDCl3): δ 0.66 (s,3H), 0.74-1.42 (m, 11H), 1.2-2.08 (m, 19H), 2.37-2.48 (m, 2H), 2.87 (s, 3H), 3.04 (dd, 1H, J=4, 13 Hz), 3.2-3.4 (m, 3H),8.12 (s, 0.8H), 8.24 (s, 0.2H); 13C NMR (CDCl3) δ 170.56, 164.54, 162.97, 68.59, 65.62, 51.99, 51.71, 44.11 ,36.85, 36.40, 34.12, 32.88, 30.64, 29.68, 29.04, 28.96, 25.20, 24.37, 22.86, 20.55, 20.21, 13.77, 12.34:. HRMS: calcd for C24H40N2O2, 388.3089; found 388.3147. ##STR12##

Provenance & Evidence