4
.2.7. N-(1-Тosylbut-1-yl)urea (4g).
Sulfone 4g (10.026 g, 96%) as a white powder was prepared from butanal (2.797 g, 38.78 mmol),
sulfinic acid 3 (6.068 g, 38.84 mmol) and urea (11.657 g, 194.08 mmol) in H O (30 mL) (rt, 2 h) as
2
–1
described for 4a in Method A. Mp 116−117 °C (decomp.); IR (Nujol) ν, cm : 3474 (s), 3364 (s), 3304
(br s), 3204 (m), 3173 (w) (NH), 1665 (vs) (amide-I), 1599 (w) (CCarom), 1587 (s), 1537 (vs) (amide-
1
II), 1497 (w) (CCarom), 1281 (vs), 1144 (vs) (SO ), 820 (s) (CH ); H NMR (300.13 MHz, DMSO-
2
arom
3
d ) δ: 7.66–7.71 (2H, m, ArH), 7.38–7.43 (2H, m, ArH), 6.83 (1H, br d, J = 10.2 Hz, NH), 5.62 (2H,
6
3
3
3
br s, NH ), 4.89 (1H, ddd, J = 11.1, J = 10.2, J = 3.2 Hz, CH-N), 2.39 (3H, s, CH in Ts), 1.87–1.98
2
3
3
(
1H, m, H in CH H ), 1.48–1.61 (1H, m, H in CH H ), 1.19–1.48 (2H, m, CH ), 0.86 (3H, t, J =
A A B B A B 2
13
7
.3 Hz, CH in Pr); C NMR (75.48 MHz, DMSO-d ) δ: 156.73 (C=O), 144.11 (C), 134.34 (C),
3 6
1
29.49 (2CH), 128.84 (2CH), 69.67 (CH-N), 28.55 (CH ), 21.08 (CH in Ts), 18.07 (CH ), 13.22 (CH
3
2
3
2
in Pr). Anal. Calcd for C H N O S: C, 53.31; H, 6.71; N, 10.36. Found: C, 53.28; H, 6.64; N, 10.21.
1
2
18
2
3
4
.2.8. N-(2-Methyl-1-tosylprop-1-yl)urea (4h).
Sulfone 4h (5.952 g, 90%) as a white powder was prepared from 2-methylpropanal (1.777 g, 24.60
mmol), sulfinic acid 3 (3.849 g, 24.64 mmol) and urea (7.392 g, 123.07 mmol) in H O (32 mL) (rt, 2
2
–
1
h) as described for 4a in Method A. Mp 120.5−122 °C (decomp.); IR (Nujol) ν, cm : 3468 (s), 3372
(s), 3263 (br s), 3196 (s) (NH), 1693 (m), 1657 (vs) (amide-I), 1612 (m) (CCarom), 1589 (s), 1539 (s)
1
(
amide-II), 1497 (w) (CCarom), 1325 (s), 1144 (s) (SO ), 822 (s) (CH ); H NMR (300.13 MHz,
2
arom
3
DMSO-d ) δ: 7.66–7.71 (2H, m, ArH), 7.36–7.42 (2H, m, ArH), 6.86 (1H, d, J = 10.8 Hz, NH), 5.71
6
3
3
3
3
(
2H, br s, NH ), 4.84 (1H, dd, J = 10.8, J = 3.4 Hz, CH-N), 2.53 (1H, doublet of septets, J = 6.8, J
2
=
3.4 Hz, CH in i-Pr, signals partly overlap with signals of the residual proton in solvent), 2.39 (3H, s,
3
3
13
CH in Ts), 1.02 (3H, d, J = 6.8 Hz, CH in i-Pr), 0.91 (3H, d, J = 6.8 Hz, CH in i-Pr); C NMR
3
3
3
(
75.48 MHz, DMSO-d ) δ: 156.89 (C=O), 143.99 (C), 135.54 (C), 129.47 (2CH), 128.49 (2CH), 73.43
6
(
CH-N), 26.67 (CH in i-Pr), 21.07 (CH in Ts), 20.42 (CH in i-Pr), 16.82 (CH in i-Pr); Anal. Calcd
3
3
3
for C H N O S: C, 53.31; H, 6.71; N, 10.36. Found: C, 53.05; H, 6.58; N, 10.50; HRMS (ESI-TOF)
1
2
18
2
3
+
m/z calcd for C H N NaO S [M+Na] 293.0936, found 293.0930. Anal. Calcd for C H N O S: C,
1
2
18
2
3
12 18
2
3
5
3.31; H, 6.71; N, 10.36. Found: C, 53.05; H, 6.58; N, 10.50.
4
.2.9. N-(1-Tosylpent-1-yl)urea (4i).
Sulfone 4i (5.058 g, 91%) as a white powder was prepared from pentanal (1.687 g, 19.58 mmol),
sulfinic acid 3 (3.065 g, 19.62 mmol) and urea (5.884 g, 97.96 mmol) in H O (38 mL) (rt, 2 h) as
2
–1
described for 4a in Method A. Mp 121.5−123 °C (decomp.); IR (KBr) ν, cm : 3435 (s), 3389 (s),
334 (s), 3284 (s), 3212 (s) (NH), 3067 (w), 3052 (w), 3032 (w) (CHarom), 1691 (s), 1649 (vs) (amide-
I), 1597 (s) (CCarom), 1521 (s) (amide-II), 1491 (w) (CCarom), 1285 (s), 1138 (s) (SO ), 827 (s)
3
2
2
7