2406
T. M. Klapo¨tke et al.
nitrite (14.0 g, 200 mmol) solution was added slowly while keeping the
temperature below 40◦C. Afterwards, urea (200 mg) was added and the
solvent was evaporated. The raw product was recrystallized from a hot
water/ethanol 1:1 mixture yielding colorless crystals (22.8 g, 85%). mp
154◦C (DSC, 5◦/min); IR (KBr, cm−1): ν˜ = 3219 (s), 3113 (s), 2990 (s),
2810 (m), 2180 (vs), 2113 (w), 1709 (s), 1602 (m), 1489 (s), 1423 (m),
1226 (s), 1152 (m), 1132 (m), 1083 (vs), 902 (w), 757 (m), 710 (m), 605
(m), 536 (w), 520 (w); Raman (200 mW, 25◦C, cm−1): ν˜ = 3073 (6), 2178
(57), 2114 (14), 1607 (4), 1485 (14), 1225 (17), 1151 (30), 1127 (13), 1083
(12), 979 (100) 905 (58), 714 (23), 653 (13), 614 (12), 520 (26), 489 (11),
474 (9), 431 (11), 231 (30); 1H NMR (d6-DMSO, 25◦C): δ = 6.42 (s, 4H,
NH2); 13C NMR (d6-DMSO): δ = 159.5 (C); Anal. Calcd for C2H8N10O4S
(268.21): C, 8.96; H, 3.01; N, 52.22. Found: C, 9.18; H, 3.04; N, 52.21%.
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