KONOVALOVA et al.
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9.99 br.s (1H, OH). Found, %: N 3.37, 3.48; S 7.50,
7.54. C24H23NO4S. Calculated, %: N 3.32; S 7.61.
5-H), 7.52 d (2H, 2″-H, 6″-H, J = 8.4 Hz), 7.86 d (2H,
3″-H, 5″-H, J = 8.4 Hz), 10.12 br.s (1H, NH).
N-[4-Hydroxy-2,6-dimethyl-3-(4-methylbenzene-
sulfonyl)phenyl]-2-phenylacetamide (XVa).
1H NMR spectrum (DMSO-d6), δ, ppm: 2.01 s (3H,
6-Me), 2.32 s (3H, 2-Me), 2.37 s (3H, 4″-CH3), 3.62 s
(2H, CH2), 6.74 s (1H, 5-H), 6.92–7.26 m (5H, Ph),
7.38 d (2H, 2″-H, 6″-H, J = 8.1 Hz), 7.74 d (2H, 3″-H,
5″-H, J = 8.1 Hz), 9.40 s (1H, NH), 10.40 s (1H, OH).
4-[2-(4-Chlorophenyl)acetylamino]-2,6-dimeth-
ylphenyl 4-methylbenzenesulfonate (XVIc). Yield
1
85%, mp 166–167°C. H NMR spectrum (DMSO-d6),
δ, ppm: 1.99 d (6H, 2-Me, 6-Me), 2.45 s (3H, 4″-CH3),
3.63 s (2H, CH2), 7.32 s (2H, 3-H, 5-H), 7.33 d (2H,
2′-H, 6′-H, J = 8.4 Hz), 7.39 d (2H, 3′-H, 5′-H, J =
8.4 Hz), 7.52 d (2H, 2″-H, 6″-H, J = 8.4 Hz), 7.84 d
(2H, 3″-H, 5″-H, J = 8.1 Hz), 10.21 br.s (1H, NH).
Found, %: N 2.54, 2.87; S 6.85, 6.93. C24H24ClNO4S.
Calculated, %: N 3.06; S 7.00.
N-[4-Hydroxy-2,6-dimethyl-3-(4-methylbenzene-
sulfonyl)phenyl]-2-(4-methylphenyl)acetamide
1
(XVb). H NMR spectrum (DMSO-d6), δ, ppm: 2.02 s
(3H, 6-Me), 2.28 s (3H, 4′-CH3), 2.32 s (3H, 2-Me),
2.37 s (3H, 4″-CH3), 3.56 s (2H, CH2), 6.74 s (1H,
5-H), 7.13 d (2H, 2′-H, 6′-H, J = 7.8 Hz), 7.23 d (2H,
3′-H, 5′-H, J = 7.5 Hz), 7.38 d (2H, 2″-H, 6″-H, J =
8.1 Hz), 7.73 d (2H, 3″-H, 5″-H, J = 8.1 Hz), 9.36 s
(1H, NH), 10.40 br.s (1H, OH).
2,6-Dimethyl-4-(2-phenoxyacetylamino)phenyl
4-methylbenzenesulfonate (XVId). Yield 100%,
1
mp 168–169°C. H NMR spectrum (DMSO-d6), δ,
ppm: 2.01 s (6H, 2-Me, 6-Me), 2.45 s (3H, 4″-CH3),
4.68 s (2H, OCH2), 6.95–7.34 m (5H, Ph), 7.39 s (2H,
3-H, 5-H), 7.53 d (2H, 2″-H, 6″-H, J = 8.1 Hz), 7.85 d
(2H, 3″-H, 5″-H, J = 8.1 Hz), 10.09 br.s (1H, NH).
Found, %: N 3.12, 3.99; S 7.10, 7.23. C24H25NO5S.
Calculated, %: N 3.19; S 7.30.
2-(4-Chlorophenyl)-N-[4-hydroxy-2,6-dimethyl-
3-(4-methylbenzenesulfonyl)phenyl]acetamide
1
(XVc). H NMR spectrum (DMSO-d6), δ, ppm: 2.05 s
(3H, 6-Me), 2.34 s (3H, 2-Me), 2.40 s (3H, 4″-CH3),
3.64 s (2H, CH2), 6.75 s (1H, 5-H), 7.23 d (2H, 2′-H,
6′-H, J = 8.4 Hz), 7.38 d (2H, 3′-H, 5′-H, J = 8.4 Hz),
7.39 d (2H, 2″-H, 6″-H, J = 8.1 Hz), 7.77 d (2H, 3″-H,
5″-H, J = 8.1 Hz), 9.42 s (1H, NH), 10.37 s (1H, OH).
N-[4-Hydroxy-2,6-dimethyl-3-(4-methylbenzene-
sulfonyl)phenyl]-3-phenylprop-2-enamide (XVe).
1H NMR spectrum (DMSO-d6), δ, ppm: 2.06 s (3H,
6-Me), 2.39 s (3H, 2-Me), 2.41 s (3H, 4″-CH3), 6.72 s
(1H, 5-H), 6.86 d (1H, CH=CH, J = 15.6 Hz), 7.39 d
(2H, 2″-H, 6″-H, J = 8.1 Hz), 7.42–7.62 m (5H, Ph),
7.77 d (2H, 3″-H, 5″-H, J = 8.1 Hz), 7.92 d (1H,
CH=CH, J = 15.9 Hz), 9.48 s (1H, NH), 10.10 s
(1H, OH).
2,6-Dimethyl-4-[(1-oxo-3-phenylprop-2-en-1-yl)-
amino]phenyl 4-methylbenzenesulfonate (XVIe).
1H NMR spectrum (DMSO-d6), δ, ppm: 2.03 s (6H,
2-Me, 6-Me), 2.46 s (3H, 4″-CH3), 6.80 d (1H,
CH=CH, J = 15.6 Hz), 7.43 s (2H, 3-H, 5-H), 7.42–
7.65 m (5H, Ph), 7.53 d (2H, 2″-H, 6″-H, J = 8.4 Hz),
7.69 d (1H, CH=CH, J = 15.6 Hz), 7.86 d (2H, 3″-H,
5″-H, J = 8.4 Hz), 10.18 br.s (1H, OH).
N-[4-Hydroxy-3,5-dimethyl-2-(4-methylbenzene-
sulfonyl)phenyl]-2-phenylacetamide (XVIIa).
1H NMR spectrum (DMSO-d6), δ, ppm: 2.19 s (3H,
5-Me), 2.30 s (3H, 3-Me), 2.36 s (3H, 4″-CH3), 3.65 s
(2H, CH2), 7.24–7.35 m (5H, Ph), 7.34 d (2H, 2″-H,
6″-H, J = 7.8 Hz), 7.46 s (1H, 6-H), 7.59 d (2H, 3″-H,
5″-H, J = 7.8 Hz), 9.80 br.s (1H, NH), 9.85 br.s
(1H, OH).
2,6-Dimethyl-4-(2-phenylacetylamino)phenyl
4-methylbenzenesulfonate (XVIa). Yield 75%,
1
mp 134–135°C. H NMR spectrum (DMSO-d6), δ,
N-[4-Hydroxy-3,5-dimethyl-2-(4-methylbenzene-
ppm: 1.99 s (6H, 2-Me, 6-Me), 2.45 s (3H, 4″-CH3),
3.61 s (2H, CH2), 7.24–7.35 m (5H, Ph), 7.33 s (2H,
3-H, 5-H), 7.51 d (2H, 2″-H, 6″-H, J = 8.4 Hz), 7.84 d
(2H, 3″-H, 5″-H, J = 8.4 Hz), 10.17 br.s (1H, NH).
Found, %: N 3.15, 3.38; S 7.65, 7.73. C24H25NO4S.
Calculated, %: N 3.31; S 7.57.
sulfonyl)phenyl]-2-(4-methylphenyl)acetamide
1
(XVIIb). H NMR spectrum (DMSO-d6), δ, ppm:
2.19 s (3H, 5-Me), 2.29 s (3H, 4′-CH3), 2.31 s (3H,
3-Me), 2.36 s (3H, 4″-CH3), 3.55 s (2H, CH2), 7.15 d
(2H, 2′-H, 6′-H, J = 7.8 Hz), 7.25 d (2H, 3′-H, 5′-H,
J = 7.8 Hz), 7.35 d (2H, 2″-H, 6″-H, J = 7.8 Hz), 7.46 s
(1H, 6-H), 7.62 d (2H, 3″-H, 5″-H, J = 7.8 Hz),
8.77 br.s (1H, NH), 9.83 br.s (1H, OH).
2,6-Dimethyl-4-[2-(4-methylphenyl)acetylamino]-
1
phenyl 4-methylbenzenesulfonate (XVIb). H NMR
spectrum (DMSO-d6), δ, ppm: 1.99 s (6H, 2-Me,
6-Me), 2.28 s (3H, 4′-CH3), 2.43 s (3H, 4″-CH3),
3.61 s (2H, CH2), 7.13 d (2H, 2′-H, 6′-H, J = 7.8 Hz),
7.23 d (2H, 3′-H, 5′-H, J = 7.5 Hz), 7.31 s (2H, 3-H,
2-(4-Chlorophenyl)-N-[4-hydroxy-3,5-dimethyl-
2-(4-methylbenzenesulfonyl)phenyl]acetamide
1
(XVIIc). H NMR spectrum (DMSO-d6), δ, ppm:
2.19 s (3H, 5-Me), 2.30 s (3H, 3-Me), 2.36 s (3H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 10 2014