BABAEVA et al.
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5-Benzylidene-2-imino-1,3-thiazolidin-4-one (I).
4-chloroaniline was heated for 1 h at 120–130°C (oil
bath). The mixture solidified and was treated with 18%
hydrochloric acid on heating for 1 h under reflux. After
cooling, the precipitate was filtered off and recrystal-
lized from methanol. Yield 62%, mp 265°C, Rf 0.42.
Found, %: C 47.38; H 3.37; N 12.12; S 14.35.
C9H7ClN2O2S. Calculated, %: C 47.69; H 3.11;
N 12.36; S 14.14.
A mixture of 32 g (0.4 mol) of thiourea, 9.5 g (0.1 mol)
of chloroacetic acid, 10.6 g (0.1 mol) of benzaldehyde,
and 30 ml of glacial acetic acid was heated for 4 h
under reflux. The mixture was cooled and made
alkaline by adding a solution of sodium carbonate, and
the precipitate was filtered off, washed with water, and
dried. Yield 80%, mp 248°C, Rf 0.39. Found, %:
C 58.93; H 3.81; N 13.65; S 15.82. C10H8N2S. Calcu-
lated, %: C 58.80; H 3.95; N 13.72; S 15.70.
2-(4-Bromophenylimino)-1,3-thiazolidin-4-one
(VIII) was synthesized in a similar way from 4-bromo-
aniline. Yield 18.6 g (73%), mp 279°C, Rf 0.54.
Found, %: C 39.62; H 2.87; Br 29.28; N 10.17.
C9H7BrN2OS. Calculated, %: C 39.87; H 2.60;
Br 29.47; N 10.33.
5-(2-Hydroxybenzylidene)-2-imino-1,3-thiazoli-
din-4-one (II) was synthesized in a similar way from
salicylaldehyde. Yield 15.2 g (69%), mp 276°C,
Rf 0.63. Found, %: C 54.71; H 3.72; N 12.61; S 14.33.
C10H8N2O2S. Calculated, %: C 54.63; H 3.66; N 13.72;
S 14.56.
1-(4-Chlorophenyl)-5-(oxiran-2-ylmethyl)imid-
azolidine-3,5-dione (IX). Metallic sodium, 4.6 g
(0.2 mol), was added in small portions under stirring to
5 ml of isopropyl alcohol. The mixture was cooled,
42 g (0.2 mol) of compound V was added, the mixture
was vigorously stirred at 70–75°C, and 18.7 g
(0.2 mol) of 2-chloromethyloxirane was added drop-
wise over a period of 20 min. The mixture was heated
for 3 h on a water bath, cooled, and filtered, and the
solvent was distilled off under reduced pressure. Yield
70%, mp 172°C, Rf 0.54. Found, %: C 54.26; H 4.06;
Cl 13.48; N 10.37. C12H11ClN2O3S. Calculated, %:
C 54.05; H 4.16; Cl 13.29; N 10.50.
5-Benzylidene-1,3-thiazolidine-2,4-dione (III).
A mixture of 9.1 g (0.1 mol) of chloroacetic acid,
10.6 g of benzaldehyde, 32 g (0.4 mol) of thiourea, and
250 ml of 33% hydrochloric acid was heated under re-
flux. After cooling, the mixture was diluted with water,
and the precipitate was filtered off, washed with water,
and dried. Yield 13.5 g (60%), mp 233°C, Rf 0.57.
Found, %: C 58.34; H 3.59; N 6.93; S 15.46.
C10H7NO2S. Calculated, %: C 58.52; H 3.44; N 6.82;
S 15.62.
5-(2-Hydroxybenzylidene)-1,3-thiazolidine-2,4-
dione (IV). Yield 16.1 g (73%), mp 285°C, Rf 0.45.
Found, %: C 54.42; H 4.47; N 6.19; S 14.28.
C10H7N2O3S. Calculated, %: C 54.29; H 3.19; N 6.33;
S 14.49.
1-(4-Bromophenyl)-5-(oxyran-2-ylmethyl)imid-
azolidine-2,4-dione (X) was synthesized in a similar
way from compound VI. Yield 65%, mp 181°C,
Rf 0,62. Found, %: C 46.17; H 3.72; Br 25.41; N 9.13.
C12H11BrN2O3. Calculated, %: C 46.32; H 3.56;
Br 25.68; N 9.00.
1-(4-Chlorophenyl)imidazolidine-2,4-dione (V).
A mixture of 5.6 g (0.1 mol) of urea, 9.5 g (0.1 mol) of
chloroacetic acid, and 12.8 g (0.1 mol) of p-chloro-
aniline was heated at 120–130°C on an oil bath. After
1 h, exothermic reaction was over, and the mixture
solidified. It was treated first with boiling water and
then with boiling methanol and filtered. A colorless
solid separated from the methanol filtrate on cooling.
Yield 62%, mp 231°C, Rf 0.36. Found, %: C 51.49;
H 3.17; Cl 16.74; N 13.52. C9H7ClN2O2. Calculated,
%: C 51.32; H 3.35; Cl 16.83; N 13.30.
1-(4-Chlorophenyl)-5-(thiiran-2-ylmethyl)imid-
azolidine-2,4-dione (XI). Thiourea, 7.6 g (0.1 mol),
was added to a solution of 25 g (0.1 mol) of compound
IX in 30 ml of ethanol, and the mixture was stirred at
60–70°C. When the initial oxirane derivative disap-
peared, the mixture was cooled, washed with water,
dried over anhydrous magnesium sulfate, and evapo-
rated under reduced pressure. Yield 72%, mp 199°C,
Rf 0.34. Found, %: C 51.12; H 3.85; N 9.82; S 11.45.
C12H11ClN2O2S. Calculated, %: C 50.98; H 3.92;
N 9.91; S 11.34.
1-(4-Bromophenyl)imidazolindine-2,4-dione (VI)
was synthesized in a similar way. Yield 16.62 g (65%),
mp 235°C, Rf 0.58. Found, %: C 42.52; H 2.44;
Br 31.12; N 10.63. C9H7BrN2O2. Calculated, %:
C 42.38; H 2.77; Br 31.33; N 10.98 .
1-(4-Bromophenyl)-5-(thiiran-2-ylmethyl)imid-
azolidine-2,4-dione (XII) was synthesized in a similar
way from compound X. Yield 22.5 g (75 %),
mp 224°C, Rf 0.47. Found, %: C 44.17; H 3.18;
N 8.36; S 9.67. C12H11N2O2S. Calculated, %: C 44.05;
H 3.39; N 8.56; S 9.80.
2-(4-Chlorophenylimino)-1,3-thiazolidin-4-one
(VII). A mixture of 7.6 g (0.1 mol) of thiourea, 9.5 g
(0.1 mol) of chloroacetic acid, and 12.8 g (0.1 mol) of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 6 2011