´
Z. BRZOZOWSKI AND J. SŁAWINSKI
1644
stirring for 26 or 18 h, respectively. After cooling to room temperature, the reaction
mixture was left to stand for 48 h. The precipitate was collected by filtration, washed
with ethanol (2 ꢂ 2 mL), and recrystallized from ethanol.
4-Dimethylamino-1Hþ-pyridinium-3-(N-formyl)sulfonamidate (5a)
Starting from DMF, the title compound 5 was obtained: 5.5 g, 60%; mp
272–273 ꢀC; IR (KBr) 2760, 2655, 2630, 1990, 1920, 1630, 1335, 1150, 1130 cmꢁ1
;
1H NMR (DMSO-d6) d 2.85 (s, 3H, N-CH3), 3.13 (s, 3H, N-CH3), 6.20 (d,
=
J ¼ 7.4 Hz, 1H, H-5), 7.24 (d, J ¼ 7.4 Hz, H-6), 8.22 (s, 1H, H-C O), 8.26 (s, 1H,
H-2), 11.82 (br.s, 1H, NHþ) ppm; 13C NMR (DMSO-d6) d 35.04, 41.22, 120.17,
128.22, 138.86, 139.57, 162.83, 173.13 ppm. Anal. calcd. for C8H11N3O3S: C,
41.91; H, 4.83; N, 18.32. Found: C, 41.98; H, 4.80; N, 18.40.
4-Diethylamino-1Hþ-pyridinium-3-(N-formyl)sulfonamidate (5b)
Starting from N,N-diethyformamide, the title compound 6 was obtained: 5.4 g,
52%; mp 241–243 ꢀC; IR (KBr) 2965, 2930, 2850, 2810, 2770, 2470, 2370, 2115, 1640,
1355, 1345, 1145, 1130 cmꢁ1
;
1H NMR (DMSO-d6) d 1.04 (t, J ¼ 7.0 Hz, 3H,
CH2CH3), 2.17 (t, J ¼ 7.0 Hz, 3H, CH2CH3), 3.34 (q, J ¼ 7.0 Hz, 2H, CH2CH3),
3.48 (q, J ¼ 7.0 Hz, 2H, CH2CH3), 6.26 (d, J ¼ 7.3 Hz, 1H, H-5), 7.76 (d, J ¼þ7.3 Hz,
=
1H, H-6), 8.26 (s, 1H, H-C O), 8.31 (s, 1H, H-2), 11.84 (s, 1H, NH ) ppm;
13C NMR (DMSO-d6) d 12.12, 14.55, 46.63, 120.14, 128.16, 138.88, 139.46, 162.13,
173.09 ppm. Anal. calcd. for C10H15N3O3S: C, 66.67; H, 5.87; N, 16.33. Found: C,
66.60; H, 5.97; N, 16.30.
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