Hydrazine → N,N',N",N"'-tetracyclohexylhydrazinedicarboximidamide

Participants

Reaction Steps

DCC (1.03 g, 4.97 mmol) was dissolved in tetrahydrofuran (15 mL). Hydrazine (135 mg, 4.22 mmol) was added via syringe. Stirring 30 hours at room temperature produced a clear yellow mixture which was evaporated to a white powder (922 mg). Solution of this powder in diethyl ether, filtration and acidification with HCl (60 mL of saturated Et2O) gave a yellow white precipitate (856 mg). Two recrystallizations (EtOH in an Et2O chamber) gave white prisms (133 mg, 18%, M.P. 288°-290° C.). The low percentage of nitrogen in the elemental analysis of this compound indicates that two equivalents of DCC have reacted to hydrazine, forming the title compound. 1H NMR ([2H]-CH3OH) δ3.21 (s, 4, N-bearing cyclohexyl), 2.0-1.5 (m, 44, cyclohexyls). 13C NMR ([2H]-CH3OH) δ154.1 (guanidine), 51.7 (N-bearing cyclohexyl), 32.4 and 24.8 (cyclohexyls). IR shows peaks at 1639 and 1589 cm-1. Elem. Analysis (C26N6 H50Cl2 : 1/2H2O). Theor. C 59.30, H 9.76, N 15.96, Found C 58.94, H 9.76, N 16.01.

Provenance & Evidence