K.M. Khan et al. / Ultrasonics Sonochemistry 21 (2014) 1200–1205
1203
119 (100), 91 (68), 77 (30). Anal. Calcd for C16H16N2O2, C = 71.62,
H = 6.02, N = 10.44. Found: C = 71.59, H = 6.01, N = 10.42.
3.2.2.10. 3-4-Dichlorobenzaldehyde-N-[-(3–4-dichlorophenyl)methyl-
idene]hydrazone (10). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d
8.68(s, 2H, –N@CH), 8.09 (dd, 2H, J2,6 = 1.8 Hz, H-2), 7.90, (dd, 2H,
J6,2 = 2.1 Hz, J6,5 = 8.4 Hz, H-6), 7.70 (d, 2H, J5,6 = 8.4 Hz, H-5), EI
MS: m/z (rel. abund.%), 346 (M+, 9), 246 (6), 199 (60), 145 (53),
3.2.2.2. 4-Methoxybenzaldehyde-N-[-(4-methoxyphenyl)methylidene]
hydrazone (2). Yield 98%; 1H NMR: (300 MHz, DMSO-d6): d 8.57 (s,
1H, –N@CH), 7.83, (d, 2H, J6,5/2,3 = 8.7 Hz, H-6/2), 7.02 (d, 2H, J5,6/
3,2 = 8.7 Hz, H-3/5), 1.41(s, 6H, CH3); EI MS: m/z (rel. abund.%),
268 (M+, 87), 241 (15), 147 (100), 77 (20). Anal. Calcd for
123 (100). Anal. Calcd for
C14H8Cl4N2, C = 48.59, H = 2.33,
N = 8.10. Found: C = 48.58, H = 2.31, N = 8.08.
C
16H16N2O2, C = 71.62, H = 6.02, N = 10.44. Found: C = 71.58,
3.2.2.11. 2-4-Dichlorobenzaldehyde-N-[-(3–4-dichlorophenyl)methyl-
idene]hydrazone (11). Yield: 98%; 1H NMR: (300 MHz, DMSO-d6): d
8.97(s, 2H, –N@CH), 8.24 (d, 2H, J6,5 = 8.4 Hz, H-6), 7.54, (dd, 2H,
J5,3 = 2.1 Hz, J5,6 = 8.4 Hz, H-5), 7.66 (d, 2H, J3,5 = 2.1 Hz, H-3), EI
MS: m/z (rel. abund.%), 346 (M+, 3), 310 (19), 274 (21), 147 (15),
H = 6.02, N = 10.40.
3.2.2.3. 3,4-Dimethoxybenzaldehyde-N-[-(3,4-dimethoxyphenyl)meth
ylidene] hydrazone (3). Yield: 98%; 1H NMR: (300 MHz, DMSO-d6):
d 8.57 (s, 2H, –N@CH), 7.72 (d, 2H, J6,5 = 7.06 Hz, H-5), 7.60 (s, 2H,
H-2), 7.37 (dd, 2H, J6,5/6,2 = 7.5 Hz, H-6), 3.87 (s, 12H, OCH3), EI MS:
m/z (rel. abund.%), 328 (M+, 38), 297 (3), 191 (54), 151 (20) 79
(100), 77 (71). Anal. Calcd for C16H16N2O2, C = 71.62, H = 6.01,
N = 10.44. Found: C = 71.60, H = 6.00, N = 10.43.
123 (100). Anal. Calcd for
C14H8Cl4N2, C = 48.59, H = 2.33,
N = 8.10. Found: C = 48.56, H = 2.31, N = 8.06.
3.2.2.12. 3-Florobenzaldehyde-N-[-(3-florophenyl)methylidene]hydra-
zone (12). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d 8.87 (s, 2H,
–N@CH), 8.16 (td, 2H, J4,5/4,2/4,6 = 7.8 H-4), 7.62, (dd, 2H, J2,4/
2,6 = 1.8 Hz, H-2), (dd, 2H, J5,6/5,4 = 7.5 Hz, H-5),7.27 (dd 2H, J6,5/
2,6 = 9.0 Hz, H-6) EI MS: m/z (rel. abund.%), 244 (M+, 42), 216 (18),
149 (100), 122 (50), 75 (61). Anal. Calcd for C14H10F2N2, C = 68.85,
H = 4.13, N = 11.47. Found: C = 68.82, H = 4.12, N = 11.46.
3.2.2.4. 3,4,5-Trimethoxybenzaldehyde-N-[-(3,4,5-trimethoxyphenyl)
methylidene] hydrazone (4). Yield: 98%; 1H NMR: (300 MHz,
DMSO-d6): d 8.57 (s, 2H, –N@CH), 7.72 (s, 2H, H-2), 7.60 (s, 2H,
H-6), (s, 18H, OCH3), EI MS: m/z (rel. abund.%), 388 (M+, 38), 257
(3), 191 (54), 151 (20) 79 (100), 77 (71). Anal. Calcd for
C
20H24N2O6, C = 61.84, H = 6.23, N = 7.21. Found: C = 61.80,
3.2.2.13. 2-Fluorobenzaldehyde-N-[-(2-fluorophenyl)methylidene] hy-
drazone (13). Yield: 88%; 1H NMR: (300 MHz, DMSO-d6): d 8.74 (s,
1H, –N@CH), 8.06 (dd, 2H, J3,4/3,5 = 8.7 Hz, H-3), 7.40 (m, 4H, H-4/5),
7.03 (t, 2H, J6,(5,7) = 7.50 Hz, H-6),; EI MS: m/z (rel. abund.%), 267
(M+, 7), 239 (100), 212 (9), 118 (76), 95 (71). Anal. Calcd for
H = 6.20, N = 7.21.
3.2.2.5. 2-Ethoxybenzaldehyde-N-[-(2-ethoxyphenyl)methylidene] hy-
drazone (5). Yield: 98%; 1H NMR: (300 MHz, DMSO-d6): d 9.04 (s,
2H, –N@CH), 8.10 (dd, 2H, J6,4 = 3 Hz J6,5 = 9 Hz, H-6), 7.47 (m, 2H,
H-4),(d, 2H, J3,4 = 8.1 Hz, H-3),(t, 2H, J5,(4,6) = 7.5 Hz, H-5), 4.21 (q,
4H, –CH2), 1.47 (t, 6H, –CH3); EI MS: m/z (rel. abund.%), 298 (M+,
9),165 (60), 135 (20), 118 (25), 74 (54). Anal. Calcd for
C14H10F2N2, C = 68.85, H = 4.13, N = 11.47. Found: C = 68.82,
H = 4.11, N = 11.45.
3.2.2.14. 2-Furaldehyde-N-[-2-furylmethylidene]hydrazone
(14). Yield: 98%; 1H NMR: (300 MHz, DMSO-d6): d 8.47(s, 2H, –
N@CH), 7.79 (d, 2H, J2,3 = 3.0 Hz, H-2), 7.06 (d, 2H, J4,3 = 3.3 Hz, H-
4), 7.54 (dd, 2H, J3,2/3,4 = 3.6 Hz, H-3); EI MS: m/z (rel. abund.%),
188 (M+, 100),131 (37), 94 (40), 52 (50). Anal. Calcd for
C
18H20N2O2, C = 72.95, H = 6.80, N = 9.45. Found: C = 72.92,
H = 6.79, N = 9.43.
3.2.2.6. 4-Ethoxybenzaldehyde-N-[-(4-ethoxyphenyl)methylidene] hy-
drazone (6). Yield 98%; 1H NMR: (300 MHz, DMSO-d6): d 8.57 (s,
1H, –N@CH), 7.83, (d, 2H, J6,5/2,3 = 8.7 Hz, H-6/2), 7.02 (d, 2H, J5,6/
3,2 = 8.7 Hz, H-3/5), 4.16 (q, J = 7 Hz, 4H, OCH2), 1.41(t, 6H, CH3);
EI MS: m/z (rel. abund.%), 296 (M+, 87), 269 (15), 175 (100), 133
(90), 120 (56), 77 (20). Anal. Calcd for C18H20N2O2, C = 72.95,
H = 6.80, N = 9.45. Found: C = 72.92, H = 6.79, N = 9.43.
C10H8N2O2, C = 63.82, H = 4.28, N = 14.89. Found: C = 63.79
H = 4.26, N = 14.85.
3.2.2.15. 3-Thiophenecarbaldehyde-N-[-3-thienylmethylidene]hydra-
zone (15). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d 8.67 (s,
2H, –N@CH), 8.10 (s, 2H, H = 2), 7.67 (d, 4H, J4,5 = 3.0 Hz, H-4),
7.54 (d, 4H, J5/4 = 3.6 Hz, H-5); EI MS: m/z (rel. abund.%), 219 (M+,
63),192 (40), 174 (35), 110 (100). Anal. Calcd for C10H8N2S2,
C = 54.52, H = 3.66, N = 12.72. Found: C = 54.50, H = 3.65, N = 12.69.
3.2.2.7. 2-Chlorobenzaldehyde-N-[2-chlorophenyl)methylidene] hydr-
azone (7). Yield: 78%; 1H NMR: (300 MHz, DMSO-d6): d 9.04 (s, 2H,
–N@CH), 8.24 (d, 2H, J3,4 = 7.8 Hz, H-3), 7.56 (m, 6H, H-4/5/6), EI
MS: m/z (rel. abund.%), 277 (M+, 5), 240 (46), 206 (47), 129 (18),
75 (100). Anal. Calcd for
N = 10.11. Found: C = 60.66, H = 3.64, N = 10.08.
C14H10Cl2N2, C = 60.67, H = 3.64,
3.2.2.16. 2-Nitrobenzaldehyde-N-[-(2-nitrophenyl)methylidene] hy-
drazone (16). Yield: 98%; 1H NMR: (300 MHz, DMSO-d6): d9.05
(s,1H, –N@CH), 8.30 (dd, 1H, J3,5 = 1.5 Hz, J3,4 7.5 Hz, H-3), 7.91
(td, 1H, J4,5/4,3 = 7.8 Hz, H-4), 7.83 (m, 2HH-5), 8.17 (dd, 1H,
J6,41.2 Hz, J6,5 = 7.8 Hz, H-6);; EI MS: m/z (rel. abund.%), 294 (M+,
6), 298 (68), 206 (22), 135 (100), 103 (40), 91 (100). Anal. Calcd
for C14H10N4O4, C = 56.38, H = 3.38, N = 18.78. Found: C = 56.36,
H = 3.36, N = 18.74.
3.2.2.8. 3-Chlorobenzaldehyde-N-[-(3-chlorophenyl)methylidene] hy-
drazone (8). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d 8.67 (s,
2H, –N@CH), 7.95(br. s, 2H, H-2), 7.93, (dd, 2H, J6,5/6,4 = 8.1 Hz, H-
6), (m, 4H, H-4/5), EI MS: m/z (rel. abund.%), 277(M+, 18), 165
(83), 138 (24), 111(60), 75 (100). Anal. Calcd for C14H10Cl2N2,
C = 60.67, H = 3.64, N = 10.11. Found: C = 60.64, H = 3.63, N = 10.09.
3.2.2.17. 3-Nitrobenzaldehyde-N-[-(3-nitrophenyl)methylidene]
hydrazone (17). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d 8.40
(s, 2H, –N@CH), 8.65 (dd. 2H, J2,4/2,6 = 1.8 Hz, H-2), 8.32, (m, 2H,
H-4), (m, 2H, H-5), (dd, 2H, J6,5/6,2 = 8.1 Hz, H-6), EI MS: m/z (rel.
abund.%), 298(M+, 24), 165(28), 118(58), 89(100). Anal. Calcd for
3.2.2.9. 4-Chlorobenzaldehyde-N-[-(4-chlorophenyl)methylidene] hy-
drazone (9). Yield: 97%; 1H NMR: (300 MHz, DMSO-d6): d 8.67 (s,
2H, –N@CH), 7.56 (d, 4H, J2,3/6,5 = 8.7 Hz, H-2/6), 7.94 (d, 4H, J3,2/
5,6 = 9 Hz, H-3/5), EI MS: m/z (rel. abund.%), 277 (M+, 6), 165 (56),
138 (21), 111 (58), 75 (100). Anal. Calcd for
C
14H10Cl2N2,
C14H10N4O4, C = 56.38, H = 3.38, N = 18.78. Found: C = 56.35,
C = 60.67, H = 3.64, N = 10.11. Found: C = 60.64, H = 3.63, N = 10.09.
H = 3.36, N = 18.75.