Compounds 12b-h were obtained analogously (12d was crystallized from DMSO).
2-(3-Chlorobenzo[b]thien-2-ylcarbonylimino)-3-phenylthiazolidin-4-one (13a).
A
mixture of
thiourea 12a (1.9 g, 5.5 mmol), monoiodoacetic acid (1 g, 5.5 mmol), and anhydrous sodium acetate (0.9 g,
11 mmol), in glacial acetic acid (30 ml) was boiled for 4 h. The mixture was cooled, the solid separated, washed
with water, and with alcohol, and recrystallized from DMF.
Compounds 13b-d were obtained analogously.
2-(3-Chlorobenzo[b]thien-2-ylcarbonylimino)-5-(3-nitrobenzylidene)-3-phenylthiazolidin-4-one (14a).
A mixture of thiourea 12a (1.04 g, 3 mmol), monoiodoacetic acid (0.56 g, 3 mmol), 3-nitrobenzaldehyde
(0.45 g, 3 mmol), and anhydrous sodium acetate (0.5 g, 6 mmol) in glacial acetic acid (25 ml) was boiled for
3.5 h. The solid was filtered off, washed with water, and with alcohol, and recrystallized from DMF. Yield 0.6 g
(38%). Mass spectrum, m/z (I, %): 519 [M]+ (20), 386 (62), 352 (10), 236 (10), 195 (100), 167 (22), 123 (11),
77 (12).
Compounds 14b,c were obtained analogously.
Mass spectra, m/z (I, %): 14b, 508 [M]+ (8), 195 (100), 167 (30), 134 (75), 132 (22), 123 (23), 90 (15),
89 (15); 14c, 553 [M]+ (3), 195 (100), 179 (13), 167 (30), 132 (30), 123 (20), 89 (30).
The 1H NMR spectra of compounds 12-14 are given in Table 2.
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