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N,N 0-Disubstituted Ethylenediamines
3201
(m, 2H), 3.30 (d, 2H), 3.65 (d, 2H), 3.73 (s, 6H), 3.95 (s, 1H), 6.75 (d, 4H),
7.10 (d, 4H), 7.50 (t, 1H), 7.90 (d, 1H), 8.17 (d, 1H), and 8.90 (s, 1H).
2-(m-Chlorophenyl)-1,3-di( p-methoxybenzyl)imidazolidine (12). M.p.:
122ꢁC (Ethanol). MS: m/z 422 (Mþ.). H NMR: ꢀ ¼ 2.50 (m, 2H), 3.10
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(m, 2H), 3.25 (d, 2H), 3.61 (d, 2H), 3.70 (s, 6H), 3.87 (s, 1H), 6.80 (d, 4H),
7.15 (d, 4H), 7.20 (m, 3H), and 7.60 (s, 1H). Anal. calcd. for
C25H27N2ClO2: C 70.99, H 6.43, N 6.62. Found: C 71.08 , H 6.35, N 6.51.
1,3-Di( p-chlorobenzyl)-2-(m-chlorophenyl)imidazolidine (16). M.p.:
81–83ꢁC (Ethanol). MS: m/z 430 (Mþ.). 1H NMR: ꢀ ¼ 2.47 (m, 2H),
3.05 (m, 2H), 3.15 (d, 2H), 3.65 (d, 2H), 3.80 (s, 1H), 7.00–7.30 (m,
10H), 7.45 (m, 1H), and 7.60 (s, 1H). Anal. calcd. for C23H21N2Cl3: C
63.98 , H 4.90, N 6.49. Found: C 64.10 , H 4.80, N 6.61.
1-Benzyl-3-( p-nitrophenyl)imidazolidine (20). Itwas obatined as
an oil.[24]
1-Benzyl-2-methyl-3-(p-nitrophenyl)imidazolidine (21). Itwas obtained
1
as an oil. MS: m/z 297 (Mþ.). H-NMR: ꢀ ¼ 1.40 (d, 3H), 2.90 (m, 1H),
3.61 (d, 1H), 3.70 (m, 2H), 3.71 (d, 1H), 3.90 (c, 1H), 4.01 (d, 1H), 6.49 (d,
2H), 7.35 (m, 5H) and 8.10 (d, 2H). Anal. calcd. for C17H19N3O2: C 68.67
, H 6.44 , N 14.13. Found: C 68.70, H 6.36, N 14.25.
1-Benzyl-2-phenyl-3-( p-nitrophenyl)imidazolidine (22). MS: m/z 359
(Mþ.). M.p.: 120–122ꢁC (Ethanol). H NMR: ꢀ ¼ 2.90 (m, 1H), 3.20 (m,
1
1H), 3.51 (d, 1H), 3.63–3.71 (m, 3H), 5.20 (s, 1H), 6.45 (d, 2H), 7.27(m,
10H) and 8.01 (d, 2H). Anal. calcd. for C22H21N3O2: C 73.52, H 5.89, N
11.69. Found: C 73.65, H 5.82, N 11.78.
1-Benzyl-2-(o-chlorophenyl)-3-( p-nitrophenyl)imidazolidine (23). MS:
m/z 393 (Mþ.). M.p.: 125–127ꢁC (Ethanol). H NMR: ꢀ ¼ 2.95 (m, 1H),
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3.20 (m, 1H), 3.61 (d, 1H), 3.71 (m, 2H), 3.97 (d, 1H), 5.70 (s, 1H), 6.40
(d, 2H), 7.30 (m, 7H), 7.45 (d, 2H) and 8.10 (d, 2H). Anal. calcd. for
C22H20N3ClO2: C 67.09, H 5.12, N 10.67. Found: C 67.20 , H 5.06,
N 10.83.
1-Benzyl-2-( p-methoxyphenyl)-3-( p-nitrophenyl)imidazolidine
(24).
MS: m/z 389 (Mþ.). M.p.: 124–125ꢁC (Ethanol). H NMR: ꢀ ¼ 2.90 (m,
1H), 3.20 (m, 1H), 3.50 (d, 1H), 3.60–3.70 (m, 3H), 3.80 (s, 3H), 5.10 (s,
1H), 6.40 (d, 2H), 6.81 (d, 2H), 7.15 (d, 2H), 7.20–7.35 (m, 5H), and 8.00
(d, 2H). Anal. calcd. for C23H23N3O3: C 70.93, H 5.95, N 10.79. Found:
C 70.77, H 6.02, N 10.87.
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ACKNOWLEDGMENT
This work was financially supported by the Universidad de Buenos
Aires and CONICET.