J Surfact Deterg
Synthesis of 4-Phenyl-5-undecyl-4H-
99.83, 31.81, 29.64, 29.35, 28.72, 26.45, 25.33, 22.68,
14.12. Anal. Calc. for C27H34BrN3OS (528.55): C, 61.35;
H, 6.48; N, 7.95; S, 6.07 %. Found: C, 61.53; H, 6.69; N,
7.64; S, 6.31 %.
1,2,4-triazole-3-thiol (9)
A mixture of thiosemicarbazide 8 (3.49 g, 0.05 mol) and
sodium hydroxide solution (1.0 g in 5 mL H2O) in ethanol
(30 mL) was heated under reflux for 4 h, then allowed to
cool. The mixture was acidified with concentrated hy-
drochloric acid and the formed solid product was filtered,
washed with water and recrystallized from ethanol. White
solid, (2.65 g, 76 %), mp. 112–114 °C. IR (m/cm-1): 3046
(CH aromatic), 2918, 2849 (CH aliphatic), 1597, 1574
(2C=N). 1H NMR: d 12.25 (s, 1H, SH), 7.58–7.32 (m, 5H,
ArH), 1.29–1.18 (m, 20H, CH2 in alkyl chain), 0.90 (t, 3H,
terminal CH3). 13C NMR: d 168.30, 152.72, 129.97,
129.02, 128.13, 127.72, 34.20, 31.76, 30.40, 29.44, 28.86,
26.10, 25.45, 22.75, 14.22. Anal. Calc. for C19H29N3S
(331.52): C, 68.84; H, 8.82; N, 12.68; S, 9.67 %. Found: C,
68.56; H, 8.66; N, 12.43; S, 9.28 %.
Synthesis of N0-Benzylidenedodecanehydrazide (12)
A solution of hydrazide 3 (2.14 g, 0.01 mol) in methanol
(10 mL) and aromatic aldehydes, e.g., benzaldehyde
(1.06 g, 0.01 mol), was heated under reflux for 4 h, using a
few drops of acetic acid. After cooling, the formed solid
product was filtered, dried and recrystallized from ethanol.
Yellow solid, (1.66 g, 78 %), mp. 90–92 °C. IR (m/cm-1):
3187 (NH), 2915, 2847 (CH aliphatic), 1669 (C=O), 1602
(C=N). 1H NMR: d 8.83 (s, 1H, NH), 8.20 (s, 1H, CH=N),
7.85–7.29 (m, 5H, ArH), 1.46–1.28 (m, 20H, CH2 in alkyl
chain), 0.93 (t, 3H, terminal CH3). Anal. Calc. for
C19H30N2O (302.45): C, 75.45; H, 10.00; N, 9.26 %.
Found: C, 75.69; H, 10.27; N, 9.02 %.
Synthesis of N-Phenyl-5-undecyl-1,3,
4-thiadiazol-2-amine (10)
Synthesis of N-(4-Oxo-2-phenylthiazolidin-3-
yl)dodecanamide (13)
Thiosemicarbazides 8 (3.49 g, 0.01 mol) was treated with
concentrated sulphuric acid (5 ml) at 0 °C in an ice bath
with constant stirring for 12 h. The reaction mixture was
poured into ice water (50 mL). The product was pre-
cipitated, filtered and washed with excess cold water. Pale
yellow solid, (1.91 g, 55 %), mp. 100–102 °C. IR (m/
cm-1): 3193 (NH), 2850, 2919 (CH aliphatic), 1618, 1550
To a stirred solution of compound 12 (3.02 g, 0.01 mol) in
dry benzene (30 mL), thioglycollic acid (0.92 g, 0.01 mol)
in dry benzene (5 mL) was added. The reaction mixture
was heated under reflux for 10 h and the excess solvent
evaporated under pressure. The obtained solid was filtered,
dried and crystallized from ethanol. Pale yellow, (2.05 g,
68 %), mp. 75–77 °C. IR (m/cm-1): 3260 (NH), 3026 (CH
aromatic), 2918, 2850 (CH aliphatic), 1716, 1665 (C=O).
1H NMR: d 7.79 (s, 1H, NH), 7.40–7.26 (m, 5H, ArH), 4.68
(s, 1H, CH of thiazole ring), 3.66, 3.81 (2 s, 2H, CH2 of
thiazole ring), 1.46–1.28 (m, 20H, CH2 in alkyl chain),
0.89 (t, 3H, terminal CH3). 13C NMR: d 176.48, 167.12,
133.83, 130.47, 129.26, 128.85, 127.73, 126.00, 63.17,
41.71, 31.79, 30.77, 29.46, 29.14, 25.61, 24.86, 22.80,
18.43, 14.23. Anal. Calc. for C21H32N2O2S (376.56): C,
66.98; H, 8.57; N, 7.44; S, 8.52 %. Found: C, 67.22; H,
8.78; N, 7.71; S, 8.81 %.
1
(C=N). H NMR: d 7.92 (s, 1H, NH), 7.41–7.26 (m, 5H,
ArH), 1.40–1.23 (m, 20H, CH2 in alkyl chain), 0.88 (t, 3H,
terminal CH3). 13C NMR: d 168.33, 153.04, 133.59,
129.89, 129.06, 128.42, 127.94, 34.43, 31.79, 29.54, 29.28,
28.84, 26.03, 25.66, 22.80, 14.73. Anal. Calc. for
C19H29N3S (331.52): C, 68.84; H, 8.82; N, 12.68; S,
9.67 %. Found: C, 69.08; H, 9.11; N, 12.46; S, 9.32 %.
Synthesis of (Z)-N0-(4-(4-Bromophenyl)-3-phenylthiazol-
2(3H)-ylidene)dodecanehydrazide (11)
A solution of hydrazide 3 (2.14 g, 0.01 mol) in ethanol
(40 mL), and p-bromophenacyl bromide (2.77 g, 0.01 mol)
was heated under reflux for 5 h. The reaction mixture was
poured on an ice-water mixture and the pH adjusted to 7
using sodium hydroxide. The solid product was collected
by filtration and crystallized from ethanol. Pale yellow
crystals, (1.56 g, 73 %), mp. 110–112 °C. IR (m/cm-1):
3332 (NH), 2851, 2919 (CH aliphatic), 1670 (CO), 1610
(C=C), 1597 (C=N). 1H NMR: d 12.41 (s, 1H, NH),
7.58–7.29 (m, 4H, ArH), 6.58 (s, 1H, CH of thiazole ring),
1.42–1.14 (m, 20H, CH2 in alkyl chain), 0.98 (t, 3H, ter-
minal CH3). 13C NMR: d 172.82, 168.09, 160.07, 142.93,
136.81, 130.14, 129.92, 128.95, 125.66, 122.61, 117.70,
Synthesis of 1-(3,5-Diamino-4,5-dihydro-1H-pyrazol-1-
yl)dodecan-1-one (14)
A mixture of hydrazide 3 (2.14 g, 0.01 mol) and mal-
ononitrile (0.66 g, 0.01 mol) was heated under reflux in
ethanol (30 mL) with a few drops of pipredine for 5 h.
After cooling, the separated product was filtered, dried and
recrystallized from ethanol. White yellow powder, (1.62 g,
76 %), mp. 99–101 °C. IR (m/cm-1): 3314–3200 (NH2),
1
2919, 2849 (CH aliphatic), 1660 (C=O), 1599 (C=N). H
NMR: d 7.79 (s, 1H, NH), 6.78 (s, 1H, CH of diazole ring),
3.90 (s, 2H, NH2), 2.52 (s, 2H, NH2), 1.71 (s, 2H, CH2 of
123