2460
C. MUKHOPADHYAY, A. DATTA, AND P. K. TAPASWI
AIL (I) which was reused several times. The IR, 1H NMR, 13C NMR, and analytical
data of all unknown compounds are given.
2,5-Dimethoxy-4’,4’’-bis(dimethylamino)-triphenylmethane
(3j). (Table 2, entry 10) Dirty white solid; mp 71 ꢁC (ethyl acetate þ petroleum ether);
1
0
0
00
00
H NMR (300 MHz, CDCl3) d: 6.96 (d, J ¼ 8.4 Hz, 4H, C3 -H, C5 -H, C3 -H, C5 -H),
0
0
00
00
6.77 (d, J ¼ 8.7 Hz, 1H, C3-H = C4-H), 6.69–6.62 (m, 5H, C2 -H, C6 -H, C2 -H, C6 -H,
C4-H=C3-H), 6.53 (d, J ¼ 3.3 Hz, 1H, C6-H), 5.72 (s, 1H, C-H), 3.65, 3.64 (two singlets
merged together, 6H, -2OMe), 2.88 (s, 12H, 2 ꢂ -NMe2); 13C NMR (75 MHz, CDCl3)
0
00
0
00
0
d: 153.4 (C2=C5), 151.6 (C5=C2), 148.8 (C1 , C1 ), 135.6 (C1), 132.6 (C4 , C4 ) 129.8 (C3 ,
0
00
00
0
0
00
00
C5 , C3 , C5 ) 117.3 (C3=C6), 112.5 (C2 , C6 , C2 , C6 ), 111.9 (C6=C3), 110.6 (C4), 56.5
(C2-OMe=C5-OMe), 55.5 (C5-OMe=C2-OMe), 47.7 (C-H), 40.7 (4 ꢂ -CH3); IR (KBr,
cmꢀ1): 2885, 1613, 1519, 1491, 1345, 1227, 1051, and 799. Anal. calcd. for
C25H30N2O2; C, 76.89; H, 7.74; N, 7.17. Found: C, 76.77; H, 7.88; N, 7.32%. MS:
m=z (%): 392.1 (31), 391.1 (M þ 1) (100%), 216.5 (6), 196.0 (88), 188.5 (36).
2,5-Dimethoxy-4’,4’’-bis(diethylamino)-triphenylmethane (3p). (Table 2,
1
Entry 16) Dirty white solid; mp 78 ꢁC (ethyl acetate þpetroleum ether); H NMR
0
0
00
00
(300 MHz, CDCl3) d: 6.93 (d, J ¼ 8.7 Hz, 4H, C3 -H, C5 -H, C3 -H, C5 -H), 6.78
(d, J ¼ 8.7 Hz, 1H, C3-H), 6.67 (dd, J ¼ 9.0 Hz and 3.0 Hz, 1H, C4-H), 6.59–6.56
0
0
00
00
(m, 5H, C2 -H, C6 -H, C2 -H, C6 -H, C6-H), 5.69 (s, 1H, C-H), 3.67, 3.66 (two singlet
merged together, 6H, 2-OMe), 3.29 (q, J ¼ 9.0 Hz, 8H, 4 ꢂ -N-CH2-CH3), 1.12 (t,
J ¼ 9.0 Hz, 12H, 4 ꢂ -N-CH2-CH3); 13C NMR (75 MHz, CDCl3) d: 153.4 (C2=C5),
0
00
0
00
0
0
00
151.7 (C5=C2), 146.1 (C1 , C1 ), 136.0 (C1), 131.5 (C4 , C4 ), 130.0 (C3 , C5 , C3 ,
00
0
0
00
00
C5 ), 117.4 (C3=C6), 112.0 (C2 , C6 , C2 , C6 ), 111.8 (C6=C3), 110.4 (C4), 56.6 (C2-
OMe=C5-OMe), 55.5 (C5-OMe=C2-OMe), 47.5 (C-H), 44.3 (4 ꢂ -N-CH2-), 12.7
(4 ꢂ -N-CH2-CH3); IR (KBr, cmꢀ1): 2968, 1608, 1512, 1357, 1265, 1199, and 795.
Anal. calcd. for C29H38N2O2; C, 77.99; H, 8.58; N, 6.27. Found: C, 77.88; H,
8.73; N, 6.41%.
3,4-Dimethoxy-4’,4’’-bis(diethylamino)-triphenylmethane (3q). (Table 2,
1
Entry 17) Light brown liquid; H NMR (300 MHz, CDCl3) d: 6.95 (d, J ¼ 8.7 Hz,
0
0
00
00
4H, C3 -H, C5 -H, C3 -H, C5 -H), 6.76 (d, J ¼ 8.4 Hz, 1H, C5-H), 6.73 (d, J ¼ 2.1 Hz,
0
0
00
00
Hz, 1H C2-H,), 6.65-6.58 (m, 5H, C6-H, C2 -H, C6 -H, C2 -H, C6 -H), 5.27 (s, 1H,
C-H), 3.84 (s, 3H, C3-OMe=C4-OMe), 3.77 (s, 3H, C4-OMe=C3-OMe), 3.31 (q,
J ¼ 7.2 Hz, 8H, 4 ꢂ -N-CH2-CH3), 1.13 (t, J ¼ 7.2 Hz, 12H, 4ꢂ-N-CH2-CH3); 13C
0
00
NMR (75 MHz, CDCl3) d: 148.6 (C3=C4), 147.1 (C4=C3), 146.1(C1 , C1 ), 138.4
0
00
0
0
00
00
(C1), 132.0 (C4 , C4 ), 130.0 (C3 , C5 , C3 , C5 ), 121.3 (C6), 112.9 (C2=C5), 111.8
0
0
00
00
(C2 , C6 , C2 , C6 ), 110.8 (C5=2), 55.9 (C3-OMe=C4-OMe), 55.8 (C4-OMe=C3-
OMe), 54.5 (C-H), 44.3 (4ꢂ -N-CH2-CH3), 12.6 (4 ꢂ -N-CH2-CH3); IR (neat, cmꢀ1):
2962, 1591, 1512, 1269, 1138, and 1022. Anal. calcd. for C29H38N2O2; C, 77.99;
H, 8.58; N, 6.27. Found: C, 77.86; H, 8.72; N, 6.41%.
4-Bromo-4’,4’’-bis(diethylamino)-triphenylmethane (3r). (Table 2, Entry
18) Light brown liquid; 1H NMR (300 MHz, CDCl3) d: 7.36 (d, J ¼ 8.4 Hz, 2H, C3-H,
0
0
C5-H), 7.02 (d, J ¼ 8.4 Hz, 2H, C2-H, C6-H), 6.91 (d, J ¼ 8.7 Hz, 4H, C3 -H, C5 -H,
00
00
0
0
00
00
C3 -H, C5 -H), 6.58 (d, J ¼ 8.7 Hz, 4H, C2 -H, C6 -H, C2 -H, C6 -H), 5.27 (s, 1H,
13
C-H), 3.31 (q, J ¼ 7.2 Hz, 8H, 4 ꢂ -N-CH2-CH3), 1.13 (t, J ¼ 7.2 Hz, 12H, 4 ꢂ -NCH2-
0
00
0
00
-CH3); C NMR (75 MHz, CDCl3) d: 146.3 (C1 , C1 ), 144.9 (C4 , C4 ), 132.4 (C1),