THIOCYANATION OF N-ARYL, N-ACETYL
641
9.80 s (1Н, ОН); Z-isomer (11%): 1.97 s (3Н, 2-Mе),
1.99 s (3Н, 5-Mе), 2.05 s (3Н, Mе), 2.35 s (3Н, 4-
MеС6Н4), 6.66 s (1Н, Н6), 6.85 s (1Н, Н3), 7.37 d (2Н,
4-MеС6Н4, Н2,6, J 8.1 Hz), 7.74 d (2Н, 4-MеС6Н4,
Н3,5, J 8.1 Hz), 9.47 s (1Н, NH), 9.95 s (1Н, ОН).
Found, %: N 8.16, 8.44; S 9.53, 9.76. C17H20N2O3S.
Calculated, %: N 8.43; S 9.65.
N-(4-Hydroxy-2-isopropyl-5-methylphenyl)-N′-
tosylacetamidine (IIIg). Yield 42%, mp 186–188°С.
1Н NMR spectrum (DMSO-d6), δ, ppm, Е-isomer
(88%): 1.03 d [6Н, СН(СН3)2, J 6.6 Hz], 2.04 s (3Н,
5-Mе), 2.34 s (3Н, 4-MеС6Н4), 2.36 s (3Н, Mе), 2.76–
2.85 m [1Н, СН(СН3)2], 6.68 s (1Н, Н3), 6.75 s (1Н,
Н6), 7.28 d (2Н, 4-MеС6Н4, Н2,6, J 8.4 Hz), 7.54 d
(2Н, 4-MеС6Н4, Н3,5, J 8.4 Hz), 9.30 s (1Н, NH), 9.83
s (1Н, ОН); Z-isomer (12%): 1.05 d [6Н, СН(СН3)2, J
6.6 Hz], 1.96 s (3Н, Mе), 2.05 s (3Н, 5-Mе), 2.38 s
(3Н, 4-MеС6Н4), 2.72–2.81 m [1Н, СН(СН3)2], 6.73 s
(1Н, Н3), 6.83 s (1Н, Н6), 7.36 d (2Н, 4-MеС6Н4, Н2,6,
J 7.8 Hz), 7.74 d (2Н, 4-MеС6Н4, Н3,5, J 7.8 Hz), 9.48
s (1Н, NH), 9.99 s (1Н, ОН). Found, %: N 7.51, 7.89;
S 8.91, 9.26. C19H24N2O3S. Calculated, %: N 7.77; S 8.90.
N-(4-Hydroxy-2,5-dimethylphenyl)-N′-(4-chloro-
phenylsulfonyl)acetamidine (IIId). Yield 64%, mp
1
180–182°С. Н NMR spectrum (DMSO-d6), δ, ppm,
Е-isomer (88%): 1.98 s (3Н, 2-Mе), 2.03 s (3Н, 5-Mе),
2.39 s (3Н, Mе), 6.60 s (1Н, Н6), 6.81 s (1Н, Н3), 7.57
d (2Н, 4-СlС6Н4, Н2,6, J 9.0 Hz), 7.69 d (2Н,
4-СlС6Н4, Н3,5, J 9.0 Hz), 9.32 s (1Н, NH), 9.95 s (1Н,
ОН); Z-isomer (12%): 1.93 s (3Н, 2-Mе, 2.00 s (3Н,
5-Mе), 2.05 s (3Н, Mе), 6.67 s (1Н, Н6), 6.86 s (1Н,
Н3), 7.64 d (2Н, 4-СlС6Н4, Н2,6, J 9.0 Hz), 7.86 d (2Н,
4-СlС6Н4, Н3,5, J 9.0 Hz), 9.49 s (1Н, NH), 10.08 s
(1Н, ОН). Found, %: N 7.53, 7.80; S 8.84, 9.09.
C16H17ClN2O3S. Calculated, %: N 7.94; S 9.09.
N-(4-Hydroxy-2-isopropyl-5-methylphenyl)-N′-
(4-chlorophenylsulfonyl)acetamidine (IIIh). Yield
1
49%, mp 170–172°С. Н NMR spectrum (DMSO-d6),
δ, ppm, Е-isomer (86%): 1.01 d [6Н, СН(СН3)2, J 6.6 Hz],
2.04 s (3Н, 5-Mе), 2.73–2.82 m [1Н, СН(СН3)2], 2.39
s (3Н, Mе), 6.67 s (1Н, Н3), 6.75 s (1Н, Н6), 7.57 d
(2Н, 4-СlС6Н4, Н2,6, J 8.1 Hz), 7.67 d (2Н, 4-СlС6Н4,
Н3,5, J 8.1 Hz), 9.33 s (1Н, NH), 9.96 s (1Н, ОН); Z-
isomer (14%): 1.05 d [6Н, СН(СН3)2, J 6.6 Hz], 2.00 s
(3Н, Mе), 2.05 s (3Н, 5-Mе), 2.70–2.80 m [1Н,
СН(СН3)2], 6.73 s (1Н, Н3), 6.85 s (1Н, Н6), 7.64 d
(2Н, 4-СlС6Н4, Н2,6, J 8.1 Hz), 7.87 d (2Н, 4-СlС6Н4,
Н3,5, J 8.1 Hz), 10.14 s (1Н, ОН), 9.50 s (1Н, NH).
Found, %: N 6.92, 7.35; S 8.30, 8.59. C18H21ClN2O3S.
Calculated, %: N 7.35; S 8.42.
N-(4-Hydroxy-5-isopropyl-2-methylphenyl)-N′-
tosylacetamidine (IIIe). Yield 50%, mp 201–202°С.
1Н NMR spectrum (DMSO-d6), δ, ppm, Е-isomer
(90%): 1.05 d [6Н, СН(СН3)2, J 6.9 Hz], 2.00 s (3Н,
2-Mе), 2.34 s (3Н, 4-MеС6Н4), 2,41 s (3Н, Mе), 3.04–
3.14 m [1Н, СН(СН3)2], 6.60 s (1Н, Н3), 6.85 s (1Н,
Н6), 7.28 d (2Н, 4-MеС6Н4, Н2,6, J 7.8 Hz), 7.58 d
(2Н, 4-MеС6Н4, Н3,5, J 7.8 Hz), 9.31 s (1Н, NH), 9.81
s (1Н, ОН); Z-isomer (10%): 1.11 d [6Н, СН(СН3)2, J
6.9 Hz], 1.98 s (3Н, 2-Mе), 1.99 s (3Н, Mе), 2.38 s
(3Н, 4-MеС6Н4), 3.04–3.14 m [1Н, СН(СН3)2], 6.67 s
(1Н, Н3), 6.86 s (1Н, Н6), 7.36 d (2Н, 4-MеС6Н4, Н2,6,
J 7.8 Hz), 7.75 d (2Н, 4-MеС6Н4, Н3,5, J 7.8 Hz), 9.51
s (1Н, NH), 9.94 s (1Н, ОН). Found, %: N 7.69, 8.12;
S 8.51, 8.88. C19H24N2O3S. Calculated, %: N 7.77; S 8.90.
N-(4-Hydroxy-2,6-dimethylphenyl)-N′-tosylace-
tamidine (IIIi). Yield 64%. 1Н NMR spectrum
(DMSO-d6), δ, ppm, Е-isomer (89%): 1.98 s (6Н,
2,6-Mе), 2.34 s (3Н, 4-MеС6Н4), 2.37 s (3Н, Mе), 6.47
s (2Н, Н3,5), 7.28 d (2Н, 4-MеС6Н4, Н2,6, J 8.4 Hz),
7.54 d (2Н, 4-MеС6Н4, Н3,5, J 8.4 Hz), 9.30 s (1Н,
NH), 9.67 s (1Н, ОН); Z-isomer (11%): 1.91 s (6Н,
2,6-Mе), 1.97 s (3Н, Mе), 2.34 s (3Н, 4-MеС6Н4), 6.53
s (2Н, Н3,5), 7.38 d (2Н, 4-MеС6Н4, Н2,6, J 7.8 Hz),
7.76 d (2Н, 4-MеС6Н4, Н3,5, J 7.8 Hz), 9.48 s (1Н,
NH), 10.08 s (1Н, ОН).
N-(4-Hydroxy-5-isopropyl-2-methylphenyl)-N′-
(4-chlorophenylsulfonyl)acetamidine (IIIf). Yield
1
71%, mp 202–203°С. Н NMR spectrum (DMSO-d6),
δ, ppm, Е-isomer (90%): 1.03 d [6Н, СН(СН3)2, J 6.9 Hz],
2.00 s (3Н, 2-Mе), 2.44 s (3Н, Mе), 3.03–3.13 m [1Н,
СН(СН3)2], 6.60 s (1Н, Н3), 6.84 s (1Н, Н6), 7.56 d
(2Н, 4-СlС6Н4, Н2,6, J 8.4 Hz), 7.71 d (2Н, 4-СlС6Н4,
Н3,5, J 8.4 Hz), 9.31 s (1Н, NH), 9.92 s (1Н, ОН); Z-
isomer (10%): 1.12 d [6Н, СН(СН3)2, J 6.9 Hz], 1.99 s
(3Н, 2-Mе), 2.00 s (3Н, Mе), 3.03–3.13 m [1Н,
СН(СН3)2], 6.68 s (1Н, Н3), 6.85 s (1Н, Н6), 7.65 d
(2Н, 4-СlС6Н4, Н2,6, J 8.4 Hz), 7.87 d (2Н, 4-СlС6Н4,
Н3,5, J 8.4 Hz), 9.50 s (1Н, NH), 10.05 s (1Н, ОН).
Found, %: N 7.33, 7.64; S 8.42, 8.73. C18H21ClN2O3S.
Calculated, %: N 7.35; S 8.42.
N-(4-Hydroxy-2,6-dimethylphenyl)-N′-(4-chloro-
phenylsulfonyl)acetamidine (IIIj). Yield 51%, mp
1
176–177°С. Н NMR spectrum (DMSO-d6), δ, ppm,
Е-isomer (89%): 1.97 s (6Н, 2,6-Mе), 2.40 s (3Н, Mе),
6.47 s (2Н, Н3,5), 7.56 d (2Н, 4-СlС6Н4, Н2,6, J 8.1 Hz),
7.65 d (2Н, 4-СlС6Н4, Н3,5, J 8.1 Hz), 9.29 s (1Н, NH),
9.79 s (1Н, ОН); Z-isomer (11%): 1.87 s (3Н, Mе),
1.91 s (6Н, 2,6-Mе), 6.53 s (2Н, Н3,5), 7.65 d (2Н,
4-СlС6Н4, Н2,6, J 8.1 Hz), 7.89 d (2Н, 4-СlС6Н4, Н3,5, J
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 5 2014