3-(Diethylamino)propyl isothiocyanate → N'-[3-(Diethylamino)propyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thiourea
Reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([N:18]([CH2:21][CH2:22][CH2:23][N:24]=[C:25]=[S:26])[CH2:19][CH3:20])[CH3:17]>C(#N)C>[CH2:19]([N:18]([CH2:16][CH3:17])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[S:26])[N:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[CH3:20]Participants
4
Procedure
A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C.