TABLE 2. 1H NMR Spectra of Products Synthesized
Com-
pound
Chemical shifts, δ, ppm (SSCC, J, Hz)
1а
1.38 (3Н, t, J = 7.0, CH2CH3); 3.11 (3H, s, N–CH3); 3.82 (3H, s, OCH3);
3.98 (2H, q, J = 7.0, OCH2CH3); 4.02 (2H, s, CH2); 4.18 (2H, s, SCH2);
6.76 (1H, d, J = 8.4, C6H3); 6.78 (2H, d, J = 8.6, C6H4); 7.04 (2H, d, J = 8.6, C6H4);
7.08 (1H, dd, J = 8.4, J = 2.2, C6H3); 7.44 (1H, d, J = 2.2, C6H3)
1c
0.99 (3H, t, J = 7.4, OCH2CH2CH2CH3); 1.49 (2H, qt, J = 7.4, J = 7.1, OCH2CH2CH2CH3);
1.73 (2H, tt, J = 7.1, J = 6.3, OCH2CH2CH2CH3); 3.11 (3H, s, N–CH3);
3.82 (3H, s, OCH3); 3.91 (2H, t, J = 6.3, OCH2CH2CH2CH3); 4.02 (2H, s, CH2);
4.18 (2H, s, SCH2); 6.75 (1H, d, J = 8.4, C6H3); 6.78 (2H, d, J = 8.6, C6H4);
7.04 (2H, d, J = 8.6, C6H4); 7.07 (1H, dd, J = 8.4, J = 2.2, C6H3);
7.45 (1H, d, J = 2.2, C6H3)
1d
1e
1.02 (6H, d, J = 6.6, OCH2CH(CH3)2); 2.04 (1H, n, J = 6.6, ОCH2CH(CH3)2);
3.11 (3H, s, N–CH3); 3.68 (2H, d, J = 6.6, OCH2CH(CH3)2); 3.82 (3H, s, OCH3);
4.03 (2H, s, CH2); 4.18 (2H, s, SCH2); 6.77 (1H, d, J = 8.4, C6H3);
6.79 (2H, d, J = 8.7, C6H4); 7.04 (2H, d, J = 8.7, C6H4);
7.08 (1H, dd, J = 8.4, J = 2.2, C6H3); 7.44 (1H, d, J = 2.2, C6H3)
3.16 (3H, s, N–CH3); 3.82 (3H, s, OCH3); 3.86 (3H, s, OCH3); 4.04 (2H, s, CH2);
4.19 (2H, s, SCH2); 6.78 (1H, d, J = 8.4, C6H3); 6.93 (1H, d, J = 8.4, C6H3);
7.08 (2H, dd, J = 8.4, C6H3); 7.42 (1H, d, J = 2.2, C6H3); 7.45 (1H, d, J = 2.2, C6H3)
1g
2
1.35 (3H, t, J = 7.0, OCH2CH3); 3.82 (3H, s, OCH3); 3.90 (2H, q, J = 7.0, OCH2CH3);
3.95 (2H, s, CH2); 4.25 (2H, s, SCH2); 6.70–7.55 (12H, m, Ar, Ph)
1.39 (3H, t, J = 7.0, OCH2CH3); 3.86 (3H, s, OCH3); 3.99 (2H, q, J = 7.0, ОCH2CH3);
4.26 (2H, s, CH2); 4.43 (2H, s, SCH2); 6.79 (2H, d, J = 8.7, C6H4);
6.91 (1H, d, J = 8.4, C6H3); 7.16 (2H, d, J = 8.7, C6H4);
7.34 (1H, dd, J = 8.4, J = 2.3, C6H3); 7.56 (1H, d, J = 2.3, C6H3)
IR spectra, νmax, cm-1: 1b) 1507 (C=N), 1c) 1573 (C=N), 1h) 1627 (C=N).
5-(3-Bromo-4-methoxybenzyl)mercapto-2-(4-ethoxybenzyl)-1,3,4-thiadiazole (2) was obtained
analogously to the above procedure from 2-(4-ethoxy-5-mercaptobenzyl)-1,3,4-thiadiazole (2.21 g, 10 mmol)
and 3-bromo-4-methoxybenzyl chloride (2.35 g, 10 mmol). IR spectrum, νmax, cm-1: 1500 (C=N).
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