Reaction #977689

Reaction equation

N-cyclohexylaniline

benzyl isothiocyanate

→

(N-cyclohexyl-N-phenylamino)-N-benzylthiocarboxamide

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe residue purified on preparative silica gel plates

Procedure

To a solution of N-cyclohexylaniline (0.1 ml, 0.57 mmol) in acetonitrile (4 ml) was added a catalytic amount of 4-(dimethylamino)pyridine (5 mg, 0.04 mmol). To this mixture was added benzyl isothiocyanate (0.11 ml, 0.83 mmol) dropwise, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, and the residue purified on preparative silica gel plates, developing with 20% ethyl acetate/hexanes, to furnish (N-cyclohexyl-N-phenylamino)-N-benzylthiocarboxamide as a white solid, (M+1)=324.8.

Source