MUSTAFAEV et al.
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washed with water, dried, and subjected to vacuum
distillation.
MRD 68.63, calcd. 67.90. H NMR spectrum, δ, ppm:
1.05 t (3H, CH3, J = 9 Hz), 3.10 d (2H, 5-CH2, J =
6 Hz), 3.90 q (2H, OCH2, J = 9 Hz), 4.00 t (1H, 5-H,
J = 9 Hz), 4.70 d (2H, NCH2, J = 9.5 Hz), 5.20 d (2H,
CH2=, J = 10.5 Hz), 5.62 m (1H, CH=). Found, %:
C 46.54; H 5.09; N 5.44; S 24.57. C10H13NO3S2. Cal-
culated, %: C 46.31; H 5.05; N 5.40; S 24.73.
Methyl (3-ethyl-2-sulfanylidene-4-oxo-1,3-thia-
zolidin-5-yl)acetate (5a). Yield 73.6 g (82%), mp 40–
42°C. 1H NMR spectrum, δ, ppm: 1.00 t (3H, CH3, J =
9 Hz), 3.10 d (2H, 5-CH2, J = 6 Hz), 3.74 q (3H,
CH3O), 4.00 t (1H, 5-H, J = 9 Hz), 4.50 q (2H, CH2N).
Found, %: C 41.28; H 4.60; N 6.04; S 27.34.
C8H11NO3S2. Calculated, %: C 41.18; H 4.75; N 6.00;
S 27.49.
Butyl [4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-
1,3-thiazolidin-5-yl]acetate (7d). Yield 86.2 g (75%),
bp 180–181°C (0.3 mm), d240 = 1.1916, nD20 = 1.5579;
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MRD 77.73, calcd. 77.15. H NMR spectrum, δ, ppm:
Methyl [4-oxo-3-(propan-2-yl)-2-sulfanylidene-
0.90 t (3H, CH3, J = 9 Hz), 1.20 m (4H, CH2), 3.00 d
(2H, 5-CH2, J = 6 Hz), 3.90 t (2H, OCH2, J = 9 Hz ),
4.20 t (1H, 5-H, J = 9 Hz), 4.65 d (2H, NCH2, J =
9 Hz), 5.30 d (2H, CH2=, J = 10 Hz), 5.65 m (1H,
CH=). Found, %: C 50.32; H 6.07; N 4.94; S 22.12.
C12H17NO3S2. Calculated, %: C 50.15; H 6.03; N 4.87;
S 22.12.
1,3-thiazolidin-5-yl]acetate (5b). Yield 79.1 g (80%),
1
mp 72.5–73.5°C. H NMR spectrum, δ, ppm: 1.40 d
[6H, (CH3)2CH, J = 9.5 Hz], 3.10 d (2H, 5-CH2, J =
6 Hz), 3.73 s (3H, OCH3), 4.00 t (1H, 5-H, J = 9 Hz),
4.60 m (1H, NCH). Found, %: C 43.84; H 5.35;
N 5.70; S 25.70. C9H13NO3S2. Calculated, %: C 43.70;
H 5.30; N 5.66; S 25.93.
Hexyl [4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-
1,3-thiazolidin-5-yl]acetate (8d). Yield 82.0 g (65%),
bp 196–197°C (0.3 mm), d420 = 1.1467, nD20 = 1.5455;
Methyl (4-oxo-3-propyl-2-sulfanylidene-1,3-
thiazolidin-5-yl)acetate (5c). Yield 84.0 g (85%),
bp 167–168°C (0.5 mm), d240 = 1.2640, nD20 = 1.5675;
MRD = 63.96, calcd. 63.74. 1H NMR spectrum, δ, ppm:
0.97 t (3H, CH3, J = 9 Hz), 1.70 q (2H, CH3CH2),
3.10 d (2H, 5-CH2, J = 6 Hz), 3.75 s (3H, CH3O),
4.00 t (1H, 5-H, J = 9 Hz), 4.50 t (2H, NCH2, J =
9.5 Hz). Found, %: C 43.90; H 5.70; N 5.80; S 25.76.
C9H13NO3S2. Calculated, %: C 43.70; H 5.30; N 5.66;
S 25.93.
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MRD 87.04, calcd. 86.30. H NMR spectrum, δ, ppm:
0.85 t (3H, CH3, J = 9 Hz), 1.20 m [6H, (CH2)4],
3.00 d (2H, 5-CH2, J = 6 Hz), 3.90 t (2H, OCH2, J =
9 Hz), 4.20 t (1H, 5-CH, J = 9 Hz), 4.70 d (2H, NCH2,
J = 9 Hz), 5.30 d (2H, CH2=, J = 10 Hz), 5.70 m
(1H, CH=). Found, %: C 53.43; H 6.78; N 4.53;
S 20.22. C14H21NO3S2. Calculated, %: C 53.30;
H 6.71; N 4.44; S 20.33.
3-(Prop-2-en-1-yl)-2-sulfanylidene-1,3-thiazoli-
dine-4-one (12). A mixture of 49.04 (0.4 mmol) of
ethyl chloroacetate and 61.68 g (0.4 mmol) of sodium
allylcarbamodithioate in ethanol was stirred for 4 h at
60–65°C. The mixture was cooled, washed with water,
and extracted with benzene. The extract was dried over
anhydrous sodium sulfate, the solvent was distilled off,
and the residue was distilled under reduced pressure.
Yield 68.6 g (64%), bp 121°C (0.5 mm), d420 = 1.3085,
nD20 = 1.6010; MRD 47.76, calcd. 63.23. 1H NMR spec-
trum, δ, ppm: 4.05 s (2H, 5-H), 4.47 d (2H, NCH2, J =
8.5 Hz), 5.42 d (2H, CH2=, J = 10.5 Hz), 5.70 m
(1H, CH=). Found, %: C 41.78; H 4.10; N 8.14;
S 37.24. C8H11NO3S2. Calculated, %: C 41.59; H 4.07;
N 8.08; S 37.01.
Methyl [4-oxo-3-(prop-2-en-1-yl)-2-sulfanyli-
dene-1,3-thiazolidin-5-yl]acetate (5d). Yield 73.5 g
(75%), bp 161–162°C (0.5 mm), d240 = 1.2972, nD20
=
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1.5884; MRD 63.67, calcd. 63.23. H NMR spectrum,
δ, ppm: 3.20 d (2H, CH2C=O, J = 6 Hz), 3.9 t (2H,
CH2CO, J = 8.5 Hz), 4.00 t (1H, 5-H, J = 9 Hz),
4.75 m (2H, CH2N), 5.10 d (2H, CH2=, J = 11 Hz),
5.60 m (1H, CH=). Found, %: C 44.25; H 4.63;
N 5.78; S 26.00. C9H11NO3S2. Calculated, %: C 44.06;
H 4.52; N 5.71; S 26.14.
Ethyl [4-oxo-3-(propan-2-yl)-2-sulfanylidene-1,3-
thiazolidin-5-yl]acetate (6b). Yield 81.5 g (78%),
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mp 60–61°C. H NMR spectrum, δ, ppm: 1.10 t (3H,
CH3, J = 9 Hz), 1.40 d [6H, (CH3)2CH, J = 9 Hz),
3.10 d (2H, 5-CH2, J = 6 Hz), 3.90 q (2H, OCH2),
4.00 t (1H, 5-H, J = 9 Hz), 4.70 m (1H, NCH). Found,
%: C 46.18; H 5.81; N 5.31; S 24.33. C10N15NO3S2.
Calculated, %: C 45.96; H 5.78; S 24.54; N 5.36.
Ethyl 3-{[(prop-2-en-1-yl)carbamothioyl]sul-
fanyl}propionate (14) was synthesized in a similar
way. After cooling, the mixture was diluted with
100 mL of water and 80 mL of benzene. The benzene
extract was dried over anhydrous sodium sulfate and
evaporated, and the residue was distilled under reduced
pressure. Yield 88%, bp 129°C (0.5 mm), d420 = 1.1445,
Ethyl [4-oxo-3-(prop-2-en-1-yl)-2-sulfanylidene-
1,3-thiazolidin-5-yl]acetate (6d). Yield 78.8 g (76%),
bp 162–163°C (0.3 mm), d240 = 1.2440, nD20 = 1.5724;
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 12 2017