ELOKHINA et al.
228
brought to boiling, it was stirred for 2.5 h, methanol was
partly evaporated, the solution was cooled to 0°C, the
precipitated crystals were filtered off, washed on the filter
with cold methanol, and dried in a vacuum. Yield 1.74 g
(91%), colorless crystals, mp 162–164°C. IR spectrum,
ν, cm–1: 585 (CS), 1430 (CH2, bend.), 1590, 1630 (C=N,
C=C), 2930 (CH2), 3440 (NH, HN+). 1H NMR spectrum,
δ, ppm: 4.38 s (2H, CH2), 6.53 s (1H, =CHBr), 7.29–
8.04 m (3H, C4H3S), 8.86 s (1H, CH=N), 10.00 br.s (1H,
NH), 10.80 br.s (1H, NH in the ring). 13C NMR spectrum,
δ, ppm: 34.62 (CH2), 87.68 (=CHBr), 128.58, 134.37,
135.25, 136.72 (Carom), 136.46 (C=CHBr), 162.04
(CH=N), 169.11 (N=CS). 15N NMR spectrum, δ, ppm:
–82.8 (CH=N), –204.0 (NH). Found, %: C 28.54; H 2.12;
Br 42.05; N 10.71; S 16.54. C9H9Br2N3S2. Calculated,
%: C 28.20; H 2.35; Br 41.78; N 10.97; S 16.71.
The reaction carried out in dioxane at microwave
activation in 4 min gave the product in 48% yield.
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2-Benzylideneazino-4-bromomethylidene-4,5-
dihydrothiazol-3-ium bromide (VIII) was obtained
similarly to compound VII from 3 g (5 mmol) of benz-
aldehyde thiosemicarbazone (II) and 0.99 g (5 mmol) of
1,3-dibromopropyne in anhydrous methanol at heating.
Yield 1.45 g (77%), colorless crystals, mp 189–190°C.
IR spectrum, ν, cm–1: 580 (CS), 1435 (CH2, bend.), 1585,
1
1640 (C=N, C=C), 2935 (CH2), 3150 (NH). H NMR
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spectrum, δ, ppm: 4.02 s (2H, CH2), 6.69 s (1H, =CHBr),
7.52–8.03 m (5H, C6H5), 8.53 s (1H, CH=N), 10.20 br.s
(1H, HN), 11.00 br.s (1H, NH in the ring). 13C NMR
spectrum, δ, ppm: 35.20 (CH2), 90.06 (=CHBr), 129.09,
129.38, 131.69, 132.82 (Carom), 135.94 (C=CHBr), 164.39
(CH=N), 169.99 (N=CS). 15N NMR spectrum, δ, ppm:
–78.3 (CH=N), –204.6 (NH). Found, %: C 35.40; H 2.98;
Br 42.34; N 10.98; S 8.30. C11H11Br2N3S. Calculated,
%: C 35.01; H 2.92; Br 42.44; N 11.14; S 8.49.
15. Kauss, V.Ya., Liepin’sh, E.E., Kalvin’sh, I.Ya., and Luke-
vits, E., Khim. Geterotsikl. Soedin., 1990, p. 120.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 2 2009