Cyclohexanemethylamine → HCID 19071297, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N'-thiocarbonyldiimidazole (Aldrich, 90%, 3.64 g, 18.4 mmol) in chloroform (20 mL) was added dropwise to a solution of cyclohexanemethylamine (Aldrich, 98%, 5.00 g, 4.33 mmol) in chloroform (10 mL). The reaction mixture was then stirred at 50° C. for 2 h, cooled to ambient temperature, and washed with hydrochloric acid (0.1N, 3×50 mL) and water (50 mL). The organic layer was dried (magnesium sulfate), and concentrated under vacuum to a yellow solid, which was recrystallized from ethanol. The mother liquor from this crystallization was concentrated, and the resulting solid was recrystallized from toluene. The two crops of crystals were combined and dried under vacuum to provide 1,3-bis(cyclohexylmethyl)thiourea as a pale yellow powder (4.19 g, 85%), m.p. 124°-125° C.; 1H-NMR (DMSO-d6) consistent with structure.

Provenance & Evidence