Synthesis, characterization, and tuberculostatic
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122.97 (Ph), 127.56 (Ph), 137.34 (Ph-CO), 149.78 (Ph-
NO2), 162.28 (C=N), 169.60 (C=O) ppm.
863 (m C–N), 719 (c C–C) cm-1; H NMR (200 MHz,
CDCl3): d = 0.77–0.98 (m, 6H, 2 CH3), 1.21–1.73 (m, 8H,
4 CH2), 2.86–3.00 (m, 4H, 2 SCH2), 3.29 (s, 3H, NCH3),
7.68 (d, 2H, Ph, J = 9 Hz), 8.19 (d, 2H, Ph, J = 8.6 Hz)
ppm; 13C NMR (50 MHz, CDCl3): d = 13.90 (CH3), 13.96
(CH3), 22.27 (CH2), 31.63 (CH2), 31.91 (SCH2), 35.14
(NCH3), 123.32 (Ph), 129.10 (Ph), 142.61 (Ph-CO), 148.81
(Ph-NO2), 163.96 (C=N), 176.11 (C=O) ppm.
4-Nitrobenzoic acid 2-[bis(phenylmethylthio)-
methylene]hydrazide (4, C21H17N3O3S2)
This product was purified by column chromatography with
chloroform as eluent. The compound was obtained as a red
solid in 50% yield (0.53 g). M.p.: 159–160 °C; IR
(KBr):vꢀ = 3,289 (m N–H), 2,924, 2,853 (m C–H), 1,689 (m
C=O), 1,552 (m NO2), 1,522, 1,497, 1,478 (m C=C), 1,337
4-Nitrobenzoic acid 2-[bis(decylthio)methylene]-1-
methylhydrazide (8, C29H49N3O3S2)
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(d C–H), 849 (m C–N), 711, 698 (c C–C) cm-1; H NMR
(200 MHz, CDCl3): d = 4.08 (s, 2H, SCH2), 4.38 (s, 2H,
SCH2), 7.03–7.37 (m, 8H, Ph), 7.52–7.67 (m, 4H, Ph), 8.24
(d, 2H, Ph, J = 8.3 Hz), 9.45 (s, 1H, NH) ppm; 13C NMR
(50 MHz, DMSO-d6): d = 36.36 (SCH2), 37.29 (SCH2),
122.98 (Ph), 127.34 (Ph), 127.41 (Ph), 128.67 (Ph), 128.93
(Ph), 129.27 (Ph), 129.36 (Ph), 129.63 (Ph), 137.66 (Ph-
CO), 146.05 (Ph-NO2), 163.85 (C=N), 174.03 (C=O) ppm.
This product was purified by column chromatography with
chloroform as eluent. The compound was obtained as a
yellow oil in 96% yield (1.32 g). IR:vꢀ = 2,924, 2,853 (m C–
H), 1,648 (m C=O), 1,601 (m C=C), 1,525 (m NO2), 1,491,
1,464 (m C=C), 1,347 (d C–H), 1,220 (m C–C), 1,071, 1,043,
994 (d C–H), 862, 850 (m C–N), 719 (c C–C) cm-1; 1H NMR
(200 MHz, CDCl3): d = 0.85–0.92 (m, 6H, 2 CH3), 1.12–
1.27 (m, 32H, 16 CH2), 2.83–2.90 (m, 4H, 2 SCH2), 3.29 (s,
3H, NCH3), 7.68 (d, 2H, Ph, J = 8.9 Hz), 8.18 (d, 2H, Ph,
J = 8.7 Hz) ppm; 13C NMR (50 MHz, CDCl3): d = 14.38
(CH3), 22.85 (CH2), 27.58 (SCH2), 28.49 (CH2), 29.31
(CH2), 29.86 (CH2), 30.05 (CH2), 31.97 (CH2), 32.11 (CH2),
39.86 (N-CH2), 122.79 (Ph), 128.52 (Ph), 142.61 (Ph-CO),
149. 76 (Ph-NO2), 162.31 (C=N), 175.89 (C=O) ppm.
4-Nitrobenzoic acid 2-[bis(methylthio)methylene]-1-
methylhydrazide (5, C11H13N3O3S2)
This compound was obtained as yellow needles in 62%
yield (0.46 g). M.p.: 98–100 °C; IR (KBr):vꢀ = 3,068,
3,046, 3,007 (m C–H), 1,642 (m C=O), 1,598 (m C=C),
1,518 (m NO2), 1,415 (m C=C), 1,348 (d C–H), 1,023, 950
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(d C–H), 870, 852 (m C–N), 718 (c C–C) cm-1; H NMR
(200 MHz, CDCl3): d = 2.32 (s, 3H, SCH3), 2.49 (s, 3H,
SCH3), 3.30 (s, 3H, NCH3), 7.71 (d, 2H, Ph, J = 8.9 Hz),
8.18 (d, 2H, Ph, J = 8.7 Hz) ppm; 13C NMR (50 MHz,
DMSO-d6): d = 13.95 (SCH3), 15.18 (SCH3), 35.20
(NCH3), 123.31 (Ph), 129.01 (Ph), 141.81 (Ph-CO),
148.26 (Ph-NO2), 166.79 (C=N), 176. 85 (C=O) ppm.
4-Nitrobenzoic acid 2-[bis(phenylmethylthio)methylene]-1-
methylhydrazide (9, C23H21N3O3S2)
This compound was obtained as colorless crystals in 65%
yield (0.73 g). M.p.: 78–79 °C; IR (KBr):vꢀ = 3,029, 2,983,
2,936 (m C–H), 1,634 (m C=O), 1,601 (m C=C), 1,520 (m
NO2), 1,481 (m C=C), 1,354, 1,340 (d C–H), 994 (m C–N),
711 (c C–C) cm-1; 1H NMR (500 MHz, CDCl3): d = 3.30
(s, 3H, NCH3), 4.25 (s, 4H, 2 SCH2), 7.28–7.38 (m, 10H, 2
Ph), 7.59 (d, 2H, Ph, J = 7.3 Hz), 8.04–8.08 (m, 2H, Ph)
ppm; 13C NMR (50 MHz, CDCl3): d = 36.00 (NCH3),
36.59 (SCH2), 122.85 (Ph), 127.70 (Ph), 128.15 (Ph),
128.59 (Ph), 128.78 (Ph), 128.88 (Ph), 129.00 (Ph), 134.82
(Ph-CH2), 141.63 (Ph-CO), 149.51 (Ph-NO2), 161.83
(C=N), 173.21 (C=O) ppm.
4-Nitrobenzoic acid 2-[bis[(1-methylethyl)thio]methylene]-
1-methylhydrazide (6, C15H21N3O3S2)
This compound was obtained as a pale yellow solid in 27%
yield (0.24 g). M.p.: 89–90 °C; IR (KBr):vꢀ = 2,961, 2,927,
2,865 (m C–H), 1,639 (m C=O), 1,600 (m C=C), 1,521 (NO2),
1,497 (m C=C), 1,352 (d C–H), 989, 866 (m C–N), 723 (c C–
C) cm-1; 1H NMR (200 MHz, CDCl3): d = 1.14 (d, 6H, 2
CH3, J = 6 Hz), 1.38 (d, 6H, 2 CH3, J = 6.7 Hz), 3.27 (s,
3H, NCH3), 3.65–3.72 (m, 2H, 2 SCH), 7.68 (d, 2H, Ph,
J = 8.8 Hz), 8.18 (d, 2H, Ph, J = 8.4 Hz) ppm; 13C NMR
(50 MHz, CDCl3): d = 21.34 (CH3), 23.94 (SCH), 40.95
(NCH3), 122.81 (Ph), 124.09 (Ph), 128.35 (Ph), 130.71
(Ph), 139.23 (Ph-CO), 148.27 (Ph-NO2), 159.93 (C=N),
172.71 (C=O) ppm.
2-[(1-Methylethyl)thio]-5-(4-nitrophenyl)-1,3,4-oxadiazole
(10, C11H11N3O3S)
Method A: the compound was synthesized from 0.45 g
4-nitrobenzohydrazide (2.5 mmol), 0.87 cm3 TEA (6.25
mmol), 0.23 cm3 CS2 (3.75 mmol), and 0.62 cm3 isopropyl
iodide (6.25 mmol) by the method described for symmet-
rical diesters 1–9. The reaction mixture was stirred for
5 days. Ice (20 g) was then added, the solution was
extracted with chloroform (3 9 10 cm3), the extract was
dried with MgSO4, and the solvent was evaporated under
vacuum. The crude product was treated with dry diethyl
ether, isolated by filtration, dried, and recrystallized from
methanol to give yellow flakes in 63% yield (0.42 g).
4-Nitrobenzoic acid 2-[bis(butylthio)methylene]-1-
methylhydrazide (7, C17H25N3O3S2)
This product was purified by column chromatography with
chloroform as eluent. The compound was obtained as a
light yellow oil in 61% yield (0.58 g). IR:vꢀ = 2,959, 2,931,
2,872 (m C–H), 1,643 (m C=O), 1,600 (m C=C), 1,523 (m
NO2), 1,348 (d C–H), 1,221 (m C–C), 1,045, 992 (d C–H),
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