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M. M. HEMDAN
acid (11), o-aminothiophenol (14a), o-aminophenol (14b), o-phenylenediamine (14c), thio-
glycolic acid (17a), 2-mercaptothanol (17b), or ethylglycinate (17c). The precipitated solid
was filtered off and recrystallized from the suitable solvent.
1-Benzoyl-4-(2-furoyl)-thiosemicarbazide (3). 86% yield; colorless crystals;
mp 140–142◦C (ethanol); IR (KBr) ν: 3300, 3206, and 3120, 1668, 1640, 1162 cm−1; 1H
NMR (DMSO-d6) δ: 6.76 (d, J = 3.4 Hz, 1H), 7.54–7.63 (m, 3H), 7.87 (d, J = 3.6 Hz,
1H), 7.79 (d, J = 6.6 Hz, 2H), 8.02 (s, 1H), 11.10 (br.s, 1H), 11.54 (br.s, 1H), 12.17 (br.s,
1H); MS (70 eV) m/z (%): 289 (M+., 30), 290 (M+.+1, 13), 291 (M+.+2, 4), 272 (22), 256
(26), 105 (100), 95 (70), 77 (29); Anal. Calcd. for C13H11N3O3S (289.31); C, 53.97; H,
3.83; N, 14.52. Found: C, 53.88; H, 3.76; N, 14.43%.
3-(2-Furoyl)-1,2,4-triazoline-5-thione (6a). 84% yield; colorless crystals; mp
>300◦C (acetic acid); IR (KBr) ν: 3283, 3118, 1670, 1170 cm−1; 1H NMR (DMSO-d6) δ
6.77 (d, J = 1.8 Hz, 1H), 7.90 (d, J = 3.6 Hz, 1H), 8.10 (s, 1H), 11.99 (br.s, 1H), 14.00
(br.s, 1H); Anal. Calcd for C6H5N3OS (167.19); C, 43.10; H, 3.01; N, 25.13. Found; C,
42.93; H, 2.86; N, 24.79%.
2-Phenyl-3-(2-furayl)-1,2,4-triazoline-5-thione (6b). 84% yield; colorless
crystals; mp 232–233◦C (toluene); IR (KBr) ν: 3106, 1635, 1171 cm−1 1H NMR
;
(DMSO-d6) δ: 6.65 (d, J = 1.8 Hz, 1H), 7.54 (d, J = 2.6 Hz, 3H,), 7.82 (d, J = 3.6 Hz,
1H), 7.91 (dd, J = 2.0, J = 3.3 Hz, 2H), 8.04 (s, 1H), 9.87 (br.s, 1H); MS m/z (%) 243
(M+., 55), 245 (M+.+2, 4), 244 (M+.+1, 11), 242 (100), 91 (72), 90 (77). Anal. Calcd for
C12H9N3OS (243.28); C, 59.24; H, 3.73; N, 17.27. Found; C, 59.19; H, 3.64; N, 17.19%.
2-(2-Furoylimino)-3-phenyl-5,5-dimethyl-1,3,4-thiadiazolidine (7). 78%
yield; mp 176–177◦C ethyl alcohol; IR (KBr) ν: 3186, 2974, 1614, 1560 cm−1; 1H NMR
(CDCl3) δ 1.95 (s, 6H), 4.3 (br.s, 1H), 6.49 (dd, J = 1.8, 2.7 Hz, 1H), 7.20 (d, J = 3.6 Hz,
1H), 7.24–7.32 (m, 1H), 7.47 (t, J = 7.4, 8.3, Hz, 2H), 7.59 (s, 1H), 7.84 (d, J = 7.8 2H);
Anal. Calcd for C15H15N3O2S (301.36) C, 59.78; H, 5.02; N, 13.94. Found: C, 59.31; H,
4.83; N, 13.44; S, 10.32%.
3-(2-Furoylamido)-3H-4H-1,2,4-triazolin-5-thione (9). 89% yield; colorless
crystals; mp 298–300◦C (acetic acid); IR (KBr) ν: 3392, 3270, 3130 (NH), 1695, 1613,
1282 cm−1; 1H NMR (DMSO-d6) δ 2.9 (br. s, 1H), 6.45–6.85 (m, 1H), 7.77–7.83 (m, 1H),
8.10 (s, 1H), 9.7 (br.s, 1H); 12.7, (br.s, 1H); MS (70 eV) m/z (%): 210 (M+., 5), 182 (11),
116 (8), 95 (100); Anal. Calcd for C7H6N4O2S (210.21); C, 40.00; H, 2.88; N, 26.65.
Found: C, 39.83; H, 2.75; N, 26.59%.
2-(3-Furan-2-carbonylthioureido)benzoic acid (12). 82% yield; colorless
crystals; mp 173◦C with decomposition, (ethanol); IR (KBr) ν: 3290, br.3170–2400,
1
1690, 1650, 1150 cm−1; H NMR (DMSO-d6) δ 6.73 (s, 1H), 7.55–7.84 (m, 4H), 7.92
(d, J = 3.6 Hz, 1H), 8.09 (s, 1H), 11.99 (br.s, 1H), 12.79 (br.s, 1H), 13.52 (br.s, 1H);
MS (70 eV) m/z (%): 290 (M+., 10), 291 (, M+.+1, 2), 262 (4), 245 (6), 95 (100); Anal.
Calcd for C13H10N2O4S (290.29); C, 53.79; H, 3.47; N, 9.65. Found: C, 53.47; H, 3.25;
N, 9.51%.
N-(Benzo[d]thiazol-2-yl)furan-2-carboxamide (16a). 65% yield; colorless
crystals, mp 188–190◦C (petroleum ether bp 60–80◦C); IR (KBr) ν: 3314, 1656, 1600
cm−1; 1H NMR (CDCl3) δ: 6.63 (s, 1H), 7.37–7.56 (m, 4H), 7.68 (d, J = 8.1 Hz, 1H), 7.87
(d, J = 7.8 Hz, 1H), 11.77 (br.s, 1H); MS (70 eV) m/z (%): 244 (M+., 23), 245 (M+.+1, 6),
246 (M+.+2, 2), 216 (47), 95 (100); Anal. Calcd for C12H8N2O2S (244.27); C, 59.00; H,
3.30; N, 11.47. Found: C, 58.96; H, 3.15; N, 11.39%.
N-(Benzo[d]oxazol-2-yl)furan-2-carboxamide (16b). 62% yield; colorless
crystals, mp 135–137◦C (petroleum ether b.p 60–80◦C); IR (KBr) ν: 3350, 1677, 1620