8
Journal of Chemical Research 00(0)
Anal. calcd for C20H16N2O2 (316.36): C, 75.93; H, 5.10; N,
8.86; found: C, 76.14; H, 5.23; N, 9.15%.
2-((4,6-Dimethylpyrimidin-2-yl)thio)-N-(3-((2-hydroxy-
benzylidene)amino)phenyl) acetamide (12a): The title
N-(3-(((2-Hydroxynaphthalen-1-yl)methylene)amino) compound separated as yellow crystals, crystallized from
phenyl)benzamide (7b): The product separated as yellow methanol, m.p. 139–140°C, yield 0.60g (65%). IR ν (cm−1):
crystals, recrystallized from n-butanol, m.p. 221–223°C, 3479 (OH), 3263 (NH), 3082 (CH aromatic), 2970 (CH ali-
yield 0.74g (86%). IR ν (cm−1): 3460 (OH), 3323 (NH), phatic), 1666 (C=O), 1605 (C=N), 1577–1543 (C=C). H
1
1
1653 (C=O), 1622 (C=N), 1593–1531 (C=C). H NMR NMR (DMSO-d6, 400MHz): δ 2.34 (s, 6H, 2 CH3), 4.07 (s,
(DMSO-d6, 400MHz): δ 7.03 (d, J=9.20Hz, 1H, aro- 2H, CH2), 6.96–7.00 (m, 3H, aromatic H), 7.13 (d,
matic H), 7.37 (t, J=8.16Hz, 1H, aromatic H), 7.49–7.63 J=7.72Hz, 1H, aromatic H), 7.38–7.47 (m, 3H, aromatic
(m, 6H, aromatic H), 7.76 (br s, 1H, aromatic H), 7.81 (d, H), 7.67–7.70 (m, 2H, aromatic H), 8.92 (s, 1H, CH=N),
J=7.92Hz, 1H, aromatic H), 7.94 (d, J=9.16Hz, 1H, aro- 10.39 (br s, 1H, NH, D2O exchangeable), 13.00 (br s, 1H,
matic H), 7.96 (s, 1H, aromatic H), 8.01 (d, J=7.48Hz, OH, D2O exchangeable). 13C NMR (DMSO-d6, 100MHz):
2H, aromatic H), 8.48 (d, J=8.44Hz, 1H, aromatic H), δ 23.8 (2 CH3), 36.0 (CH2), 112.9, 116.2, 116.5, 117.1,
9.66 (s, 1H, CH=N), 10.40 (br s, 1H, NH, D2O exchange- 118.0, 119.6, 119.7, 130.3, 133.0, 133.8, 140.5, 149.0,
able), 15.78 (br s, 1H, OH, D2O exchangeable). 13C NMR 160.7, 163.8, 167.3, 167.4 (aromatic carbons), 169.7
(DMSO-d6, 100MHz): δ 108.9, 113.3, 115.4, 118.8, (C=N), 192.0 (C=O). MS (EI): m/z (%)=392 (M+, 44.38),
120.6, 122.8, 124.0, 127.1, 128.1, 128.7, 128.9, 129.5, 181 (100). Anal. calcd for C21H20N4O2S (392.48): C, 64.27;
130.4, 132.2, 133.6, 135.2, 137.6, 140.8, 144.5, 155.8 H, 5.14; N, 14.28; found: C, 64.49; H, 5.26; N, 14.49%.
(aromatic carbons), 166.2 (C=N), 171.4 (C=O). MS (EI):
2-((4,6-Dimethylpyrimidin-2-yl)thio)-N-(3-(((2-hydrox-
m/z (%)=366 (M+, 89.97), 59 (100). Anal. calcd for ynaphthalen-1-yl)methylene) amino)phenyl)acetamide (12b):
C24H18N2O2 (366.42): C, 78.67; H, 4.95; N, 7.65; found: The obtained product separated as yellow crystals, crystalized
C, 79.01; H, 5.12; N, 7.88%.
from n-butanol, m.p. 204–206°C, yield 0.70g (67%). IR ν
N-(3-((2-Hydroxybenzylidene)amino)phenyl)-2-pheny- (cm−1): 3444 (OH), 3294 (NH), 3059–3032 (CH aromatic),
lacetamide (7c): The title compound was obtained as yellow 2997–2920 (CH aliphatic), 1666 (C=O), 1620 (C=N), 1578–
crystals, recrystallized from n-butanol, m.p. 195–197°C, 1535 (C=C). 1H NMR (DMSO-d6, 400MHz): δ 2.35 (s, 6H,
yield 0.61g (78%). IR ν (cm−1): 3450 (OH), 3260 (NH), CH3), 4.09 (s, 2H, CH2), 6.98 (s, 1H, aromatic H), 7.01 (d,
3047–3026 (CH aromatic), 2993–2920 (CH aliphatic), 1661 J=9.20Hz, 1H, aromatic H), 7.34 (t, J=7.20Hz, 1H, aro-
(C=O), 1622 (C=N), 1589–1533 (C=C). 1H NMR matic H), 7.44–7.47 (m, 3H, aromatic H), 7.55 (t, J=7.08Hz,
(DMSO-d6, 400MHz): δ 3.67 (s, 2H, CH2), 6.97–7.00 (m, 1H, aromatic H), 7.76 (br s, 1H, aromatic H), 7.80 (d,
2H, aromatic H), 7.12 (d, J=7.84Hz, 1H, aromatic H), 7.26 J=7.48Hz, 1H, aromatic H), 7.94 (d, J=9.20Hz, 1H, aro-
(t, J=6.40Hz, 1H, aromatic H), 7.32–7.44 (m, 6H, aromatic matic H), 8.45 (d, J=8.44Hz, 1H, aromatic H), 9.61 (s, 1H,
H), 7.49 (d, J=8.20Hz, 1H, aromatic H), 7.67–7.71 (m, 2H, CH=N), 10.41 (br s, 1H, NH, D2O exchangeable), 15.70 (br s,
aromatic H), 8.92 (s, 1H, CH=N), 10.32 (br s, 1H, NH, D2O 1H, OH, D2O exchangeable). 13C NMR (DMSO-d6,
exchangeable), 13.02 (br s, 1H, OH, D2O exchangeable). 100MHz): δ 23.7 (2 CH3), 35.9 (CH2), 108.8, 112.0, 115.0,
13C NMR (DMSO-d6, 100MHz): δ 43.8 (CH2), 112.8, 116.6, 117.6, 120.5, 122.8, 124.1, 127.1, 128.8, 129.5, 130.6,
116.2, 117.1, 118.0, 119.6, 119.7, 127.0, 128.8, 129.6, 130.2, 133.5, 137.7, 140.5, 144.4, 155.6, 167.5, 169.6 (aromatic car-
133.0, 133.8, 136.3, 140.7, 149.0, 160.7 (aromatic carbons), bons), 171.7 (C=N), 193.4 (C=O). MS (EI): m/z (%)=442
163.8 (C=N), 169.8 (C=O). MS (EI): m/z (%)=330 (M+, (M+, 70.74), 153 (100). Anal. calcd for C25H22N4O2S
100). Anal. calcd for C21H18N2O2 (330.39): C, 76.34; H, (442.54): C, 67.85; H, 5.01; N, 12.66; found: C, 67.53; H,
5.49; N, 8.48; found: C, 76.49; H, 5.67; N, 8.67%.
5.24; N, 12.48%.
N-(3-{[(2-Hydroxynaphthalen-1-yl)methylidene]
(2E)-1-{3-[(2-Hydroxybenzylidene)amino]phenyl}-3-
amino}phenyl)-2-phenylacetamide (7d): The product was phenylprop-2-en-1-one (16a): The title compound sepa-
obtained as yellow crystals, recrystallized from n-butanol, rated as pale yellow crystals on cooling the reaction
m.p. 194–196°C, yield 0.72 g (80%). IR ν (cm−1): 3441 mixture, recrystallized from 90% ethanol, m.p. 115–
(OH), 3287 (NH), 3055–3028 (CH aromatic), 2943 (CH 117°C, yield 0.61g (79%). IR ν (cm−1): 3419 (OH), 3062–
aliphatic), 1662 (C=O), 1627 (C=N), 1589–1535 (C=C). 3022 (CH aromatic), 1662 (C=O), 1618 (C=N), 1607–1574
1H NMR (DMSO-d6, 400 MHz): δ 3.69 (s, 2H, CH2), 7.01 (C=C). 1H NMR (DMSO-d6, 400MHz): δ 7.02 (t,
(d, J = 9.16 Hz, 1H, aromatic H), 7.26–7.42 (m, 8H, aro- J=8.12Hz, 2H, aromatic H), 7.44–7.49 (m, 4H, aromatic
matic H), 7.51–7.55 (m, 2H, aromatic H), 7.78–7.81 (m, H), 7.65–7.74 (m, 3H, aromatic H), 7.81 (d, J=15.60Hz,
2H, aromatic H), 7.94 (d, J = 9.24 Hz, 1H, aromatic H), 1H, ethylenic H), 7.93–7.95 (m, 2H, aromatic H), 8.03 (d,
8.45 (d, J = 8.48 Hz, 1H, aromatic H), 9.60 (s, 1H, CH=N), J=15.60Hz, 1H, ethylenic H), 8.09 (d, J=7.44Hz, 1H,
10.35 (br s, 1H, NH, D2O exchangeable), 15.71 (br s, 1H, aromatic H), 8.18 (s, 1H, aromatic H), 9.08 (s, 1H, CH=N),
OH, D2O exchangeable). 13C NMR (DMSO-d6, 100 MHz): 12.90 (br s, 1H, OH, D2O exchangeable). 13C NMR
δ 43.8 (CH2), 108.8, 112.0, 115.0, 117.6, 120.5, 122.8, (DMSO-d6, 100MHz): δ 117.1, 119.7, 119.8, 121.6,
124.0, 127.0, 127.1, 128.71, 128.74, 128.8, 129.5, 129.6, 122.5, 126.7, 127.2, 129.2, 129.4, 129.5, 130.4, 131.2,
130.5, 133.5, 136.2, 137.6, 140.8, 144.5, 155.7 (aromatic 133.2, 134.0, 135.1, 139.3, 144.9, 149.3, 160.8, 165.1
carbons), 170.0 (C=N), 171.6 (C=O). MS (EI): m/z (aromatic carbons), 189.3 (C=N), 192.3 (C=O). MS (EI):
(%) = 380 (M+, 100). Anal. calcd for C25H20N2O2 m/z (%)=327 (M+, 100). Anal. calcd for C22H17NO2
(380.45): C, 78.93; H, 5.30; N, 7.36; found: C, 78.70; H, (327.38): C, 80.71; H, 5.23; N, 4.28; found: C, 80.53; H,
5.49; N, 7.68%.
5.60; N, 4.32%.