Journal of the Iranian Chemical Society
absolute ethanol (50 ml)) for 3 h. The reaction mixture was
then cooled, poured into cold water and neutralized with
dil HCl. The separated solid was then fltered of, dried and
recrystallized from ethanol to give 8 as pale yellow crystals.
m.p. 220–222 °C, Yield: 72%. IR (KBr, cm−1) υmax: 3286
(NH), 1689, 1651 (C=O) cm−1. 1H NMR (DMSO-d6) δ (ppm):
6.51–7.85 (m, 7H, furan-H+phenyl-H), 10.27 (s, 1H, NH).
13C NMR (DMSO-d6) δ (ppm): 112.77, 118.56, 127.00,
129.03, 129.47, 135.24, 145.09, 148.80, 151.75, 157.27,
168.47, 176.35. Anal. Calc. for C14H8N4O3 (280.24): C, 60.00;
H, 2.88; N, 19.99; Found: C, 60.11; H, 2.79; N, 19.86.
for 6 h. The reaction mixture was then cooled and poured
into cold water, and the solid obtained was fltered of, dried
and recrystallized from ethanol to give 11 as pale yellow
crystals.
m.p. 184–186 °C, Yield: 88%. IR (KBr, cm−1) υmax
:
3275, 3124 (NH), 1685, 1663 (C=O), 1269 (C=S) cm−1.
1H NMR (DMSO-d6) δ (ppm): 7.16–8.03 (m, 7H, furan-
H+Aryl-H), 11.75 (s, 1H, NH), 12.17 (s, 1H, NH), 12.97
(s, 1H, COOH). 13C NMR (DMSO-d6) δ (ppm): 113.19,
118.00, 125.12, 126.77, 127.86, 130.93, 133.78, 138.52,
145.10, 148.87, 167.58, 168.40, 179.78. Anal. Calc. for
C13H10N2O4S (290.30): C, 53.79; H, 3.47; N, 9.65; Found:
C, 53.87; H, 3.58; N, 9.55.
N‑[6‑(furan‑2‑yl)‑4‑sulfanylidene‑3,4‑di‑
hydro‑2H‑1,3,5‑oxadiazin‑2‑ylidene]urea (9)
3‑(Furan‑2‑carbonyl)‑2‑sulfanylidene‑2,3‑dihydro‑
quinazolin‑4(1H)‑one (12)
A mixture of compound 1 (0.01 mol) and biuret (0.01 mol)
in dioxane (50 ml) was heated under refux for 8 h. The reac-
tion mixture was concentrated then cooled and poured into
cold water, and the precipitate formed was fltered of, dried
and recrystallized from ethanol to give 8 as brown crystals.
A mixture of compound 11 (0.01 mol) and Ac2O (20 ml)
was heated under refux for 4 h. The reaction mixture was
then cooled, and the solid obtained was fltered of, dried
and recrystallized from ethanol to give 12 as white crystals.
m.p. 264–266 °C, Yield: 81%. IR (KBr, cm−1) υmax: 3209
(NH), 1658 (C=O), 1273 (C=S) cm−1. 1H NMR (DMSO-
d6) δ (ppm): 7.50–8.05 (m, 7H, furan-H+quinazoline-H),
11.90 (s, 1H, NH). 13C NMR (DMSO-d6) δ (ppm): 112.45,
119.82, 124.74, 127.44, 129.33, 132.24, 136.75, 145.07,
148.02, 153.35, 169.28, 171.32, 185.02. Anal. Calc. for
C13H8N2O3S (272.28): C, 57.35; H, 2.96; N, 10.29; Found:
C, 57.44; H, 2.87; N, 10.35.
m.p. 182–184 °C, Yield: 83%. IR (KBr, cm−1) υmax
:
3336, 3209 (NH, NH2), 1670 (C=O), 1265 (C=S) cm−1.
1H NMR (DMSO-d6) δ (ppm): 6.72–8.02 (m, 3H, furan-H),
9.66 (s, 2H, NH2), 11.16 (s, 1H, NH). 13C NMR (DMSO-d6)
δ (ppm): 113.07, 118.84, 145.21, 148.59, 157.65, 166.02,
170.45, 181.99. Anal. Calc. for C8H6N4O3S (238.23): C,
40.34; H, 2.54; N, 23.52; Found: C, 40.41; H, 2.44; N, 23.63.
1‑Benzoyl‑5‑[(4‑chlorophenyl)methylidene]‑3‑(fur
an‑2‑carbonyl)‑2‑sulfanylideneimidazolidin‑4‑one
(10)
N‑[(1,3‑thiazol‑2‑yl)carbamothioyl]furan‑2‑car‑
boxamide (13a) and N‑(phenylcarbamothioyl)
furan‑2‑carboxamide (13b)
A mixture of compound 1 (0.01 mol), hippuric acid
(0.01 mol) and p-chlorobenzaldehyde (0.01 mol) in dry pyri-
dine (15 ml) was heated under refux for 5 h. The reaction
mixture was then cooled, poured into cold water and neutral-
ized with dil HCl. The solid obtained was fltered of, dried
and recrystallized from ethanol to give 10 as yellow crystals.
General method
A mixture of compound 1 (0.01 mol) and 2-aminothiazole or
aniline (0.01 mol) in dry acetone (50 ml) was stirred at room
temperature for 3 h. The reaction mixture was then poured
into cold water, and the separated precipitate was fltered of,
dried and recrystallized from the proper solvent to give 13a
and 13b, respectively.
m.p. 190–192 °C, Yield: 69%. IR (KBr, cm−1) υmax
:
1
1697, 1654 (C=O), 1234 (C=S) cm−1. H NMR (DMSO-
d6) δ (ppm): 7.38–8.35 (m, 13H, furan-H+phenyl-H+Aryl-
H + exocyclic vinylic-H). 13C NMR (DMSO-d6) δ (ppm):
113.62, 115.21, 118.42, 125.36, 127.04, 128.53, 129.59,
129.81, 132.53, 133.00, 133.98, 134.24, 134.33, 136.35,
145.25, 148.46, 163.70, 165.39, 167.20, 180.83. Anal. Calc.
for C22H13ClN2O4S (436.88): C, 60.49; H, 3.00; N, 6.41;
Found: C, 60.56; H, 3.09; N, 6.35.
Compound 13a
From water as yellow crystals, m.p. 120–122 °C, Yield:
85%. IR (KBr, cm−1) υmax: 3336, 3113 (NH), 1666 (C=O),
1253 (C=S) cm−1. 1H NMR (DMSO-d6) δ (ppm): 6.73–8.11
(m, 5H, furan-H+thiazole-H), 10.94 (s, 1H, NH), 12.61 (s,
1H, NH). 13C NMR (DMSO-d6) δ (ppm): 112.73, 114.30,
118.76, 137.92, 145.29, 148.67, 169.21, 177.84, 182.07.
Anal. Calc. for C9H7N3O2S2 (253.30): C, 42.68; H, 2.79; N,
16.59; Found: C, 42.75; H, 2.68; N, 16.46.
2‑{[(Furan‑2‑carbonyl)carbamothioyl]amino}ben‑
zoic acid (11)
A mixture of compound 1 (0.01 mol) and anthranilic acid
(0.01 mol) in dry acetone (50 ml) was heated under refux
1 3