1296
N
H
N
O S
CH
2
CH
3
CH
2
CH
3
CuI
N
N
O
S
H
3
CH
2
C
CH
2
CH
3
Cu
N
N
O
S
CH
2
CH
3
H
3
CH
2
C
Complex
Cu-1
+
N
-Benzoyl-
N ,N'
-diethylthiourea (
1
)
'
(C=S) 1233 (s).
1
H-NMR
(300 MHz, CDCI
3
): 1.32 (m, 6H, 2CH
3
), 3.60 (q, 2H, CH
2
), 4.04 (q, 2H, CH
2
), 7.46 (t,
2H,
m
-Ph), 7.57 (t, 1H,
p
-Ph), 7.84 (d, 2H,
o
-Ph), 8.60 (s, 1H, NH).
13
C-NMR (75.5 MHz, CDCI
3
): 11.91, 13.68
(2CH
3
); 48.12(2CH
2
); 128..29, 129.21, 132.99, 133.27 (6C-Ph); 164.30 (C=O), 179.8 (C=S).
O
Cl
NH
4
SCN
Al
2
O
3
a and b = MW or Ref lux
O
NCS
H
N
N
H
N
O S
(
1
)
+
Benzoyl chloride
N
-Benzoyl-
N ',N'
-diethylthiourea
Benzoyl isothiocyanate
'
'
Acetone
a
b
a and b = MW 76.6%
a and b = Ref lux 74.2 %
2.
¨µ¦´
Á¦µ³®r
1-Benzoyl-3-[2-(3-benzoyl-thioureido)-ethyl]-thiourea (2)
O
Cl
NH
4
SCN
Al
2
O
3
a and b = MW or Ref lux
O
NCS
+
Benzoyl chloride
Benzoyl isothiocyanate
Acetone
a
b
N
H
N
H
O S
H
N
H
N
S O
1-Benzoyl-3-[2-(3-benzoyl-thioureido)-ethyl]-thiourea
H
2
N
NH
2
(
2
)
N
H
N
H
O S
NH
2
a and b = MW 64.8%
a and b = Reflux 68.2%
µ¦´
Á¦µ³®r
µ¦
2
µ benzoyl chloride (0.003 mol), ammonium thiocyanate (0.003 mol) ¨³
ethylenediamine (0.002 mol) £µ¥Äo
¦´
¸
ŤæÁª¢ (10% power, 800w) ¦ª¤Áª¨µµ¦µ¥¦´
¸
8 µ¸
Åo
µ¦
2
Á}
°Â
È
¸
Á®¨º
°°n
° 0.375 ¦´
¤, 64.8 %) ¨³Å¤n
µ¤µ¦Â¥µ¦´
ª¨µÅo
µ¦¦¸
¢¨´
r
Ä´
ªÎ
µ¨³¨µ¥Â°¸
ÃåĮo
ªµ¤¦o
°o
ª¥ÁµÅ¢¢j
µ ¦ª¤ 5 ´É
ªÃ¤Ä®o
¨·
£´
r
2
(0.3950
g, 68.2%) »
®¨°¤Á®¨ª 265.2-268.9 °«µÁ¨Á¸
¥ IR
(KBr, cm
-1
): (N-H) 3421 cm
-1
(sh), (C=O) 1666 cm
-1
(vs),
(C=S) 1267(s).
1
H-NMR
(300 MHz, CDCI
3
): 4.117 (t, 4H, 2CH
2
), 7.511
(t, 2H,
m
-Ph),
7.627 (t, 1H,
p
-Ph),
7.826
(d, 2H,
o
-Ph)
,
9.04 (s, 2H, 2NH), 10.92(s, 2H, 2NH).
13
C-NMR (75.5 MHz, CDCI
3
): 43.66(2CH
2
); 127.49
,
129.21,
131.99, 133.27
(6C-Ph); 166.76 (C=O), 181.15 (C=S).
¨µ¦´
Á¦µ³®r
µ¦¦³°Á·
o
°°Á°¦r
1. ¨µ¦´
Á¦µ³®r
µ¦¦³°Á·
o
°Cu-1
