558
ROSENTSVEIG et al.
1.14 g (0.015 mol) of thiourea. Yield of amide Vb
was 2.98 g.
precipitate was filtered off and washed with tetra-
chloromethane. Yield of amide VIII was 1.47 g.
N-(1-Benzenesulfonamido-2-phenyl-2, 2-di-
chloroethyl)thiocarbamide (VIa). A mixture of
1.64 g (0.005 mol) of compound IIa and 0.38 g
(0.005 mol) of thiourea in 10 ml of benzene was
stirred for 6 h. Then the solvent was evaporated, the
solid residue was washed with water and recrystalliz-
ed from ethanol. Yield of amide VIa was 1.78 g.
N-(1-Benzenesulfonamido-2-phenyl-2,2-dichloro-
ethyl)-N -acetylthiocarbamide (IXa). A mixture of
1.64 g (0.005 mol) of compound IIa and 0.59 g
(0.005 mol) of acetylthiourea in 10 ml of benzene was
stirred while heating at reflux for 4 h. Then the
solvent was evaporated, and the residue was re-
crystallized from ethano. Yield of amide IXa was
1.43 g.
N-[1-(4-Chlorobenzene)sulfonamido-2-phenyl-
2,2-dichloroethyl]thiocarbamide (VIb) was obtained
as described above from 1.81 g (0.005 mol) of com-
pound IIb and 0.38 g (0.005 mol) of thiourea. Yield
of amide VIb was 1.93 g.
N-[1-(4-Chlorobenzene)sulfonamido-2-phenyl-
2,2-dichloroethyl]-N -acetylthiocarbamide
(IXb)
was obtained analogously from 1.81 g (0.005 mol) of
compound IIb and 0.59 g (0.005 mol) of acetylthio-
urea. Yield of amide IXb was 1.66 g.
N,N -Bis(1-benzenesulfonamido-2,2,2-trichloro-
ethyl)thiocarbamide (VIIa). A mixture of 11.3 g
(0.05 mol) of N-dichlorobenzenesulfonamide and
26.91 ml (0.3 mol) of trichloroethylene was stirred
at 87 C for 9 h. Then the reaction mixture was
cooled to 35 C, and by portions was added thereto
1.90 g (0.025 mol) of thiourea. Yield of compound
VIIa was 15.74 g.
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N,N -Bis(1-benzenesulfonamido-2-phenyl-2,2-
dichloroethyl)thiocarbamide (VIIb). To a solution
of 1.64 g (0.005 mol) of compound IIb in 10 ml of
benzene was added 0.19 g (0.0025 mol) of thiourea.
The reaction mixture was stirred at heating to 80 C
for 8 h. Then the benzene was evaporated, the residue
was dissolved in acetone and precipitated into water.
The resin formed was separated by decanting, stored
for a week at cold, and recrystallized from ethanol.
Yield of compound VIIb was 1.56 g.
N-[1-(4-Chlorobenzene)sulfonamido-2,2,2-tri-
chloroethyl]-N -acetylthiocarbamide (VIII). To a
solution of compound Ib in trichloroethylene, pre-
pared from 1.30 g (0.005 mol) of dichloroamide of
chlorobenzenesulfonic acid [5] was added 0.59 g
(0.005 mol) of acetylthiourea. The reaction mixture
was stirred at heating to 70 80 C for 1 h and then left
standing for 24 h at room temperature.. The separated
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 39 No. 4 2003