The Journal of Organic Chemistry
Article
ppm; anal. calcd for C16H19NO2S: C 66.41, H 6.62, N 4.84, S 11.08.
Found: C 66.34, H 6.68, N 4.92, S 10.89.
N-(4-Bromophenyl)-N-methylbenzenesulfonamide (3f). It was
N-Methyl-N-phenylnaphthalene-2-sulfonamide (3n). It was
obtained in 85% yield (252.7 mg); white solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
obtained in 93% yield (303.4 mg); light yellow liquid; TLC
(petroleum ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz,
8.07 (d, 1H, J = 1.5 Hz), 7.75−7.81 (m, 3H), 7.48−7.57 (m, 2H),
7.38 (dd, 1H, J = 8.6, 2.0 Hz), 7.16−7.20 (m, 3H), 6.99−7.04 (m,
2H), 3.12 (s, 3H) ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 137.4,
133.2, 132.5, 131.3, 130.9, 130.6, 129.4, 128.8, 127.9, 127.0, 125.7,
124.2, 113.1, 113.1, 39.9 ppm; anal. calcd for C17H15NO2S: C 68.66,
H 5.08, N 4.71, S 10.78. Found: C 68.71, H 5.12, N 4.67, S 10.74.
N-Methyl-N-(p-tolyl)naphthalene-2-sulfonamide (3o). It was
obtained in 88% yield (274.0 mg); white solid; TLC (petroleum
1
CDCl3): δ 7.51−7.55 (m, 3H), 7.40 (d, 2H, J = 7.2 Hz), 7.34 (d, 2H,
J = 8.7 Hz), 6.89 (d, 2H, J = 8.7 Hz), 3.07 (s, 3H) ppm; 13C{1H}
NMR (100 MHz, CDCl3): δ 140.5, 136.0, 133.0, 132.0, 128.9, 128.8,
128.1, 127.8, 38.0 ppm; anal. calcd for C13H12BrNO2S: C 47.87, H
3.71, N 4.29, S 9.83. Found: C 47.91, H 3.69, N 4.33, S 12.25.
4-Chloro-N-methyl-N-phenylbenzenesulfonamide (3g). It was
obtained in 90% yield (253.5 mg); white solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
8.14 (s, 1H), 7.81−7.86 (m, 3H), 7.50−7.62 (m, 2H), 7.44 (dt, 1H, J
= 8.7, 2.0 Hz), 7.03 (d, 2H, J = 8.2 Hz), 6.92 (dd, 2H, J = 8.5, 2.0
Hz), 3.15 (s, 3H), 2.28 (s, 3H) ppm; 13C{1H} NMR (100 MHz,
CDCl3): δ 138.9, 137.4, 134.8, 133.8, 132.0, 129.6, 129.2, 129.1,
128.8, 128.8, 127.9, 127.4, 126.7, 123.3, 38.4, 21.1 ppm; anal. calcd
for C18H17NO2S: C 69.43, H 5.50, N 4.50, S 10.30. Found: C 69.52,
H 5.57, N 4.44, S 10.23.
7.31−7.41 (m, 4H), 7.20−7.24 (m, 3H), 6.99−7.03 (m, 2H), 3.10 (s,
3H) ppm; 13C{1H} NMR (100 MHz, CDCl3): δ 140.2, 138.4, 134.0,
128.3, 128.1, 128.1, 126.6, 125.6, 37.2 ppm; anal. calcd for
C13H12ClNO2S: C 55.42, H 4.29, N 4.97, S 11.38. Found: C 55.46,
H 4.31, N 5.02, S 11.31.
4-Chloro-N-methyl-N-(p-tolyl)benzenesulfonamide (3h). It was
obtained in 92% yield (272.1 mg); white solid; TLC (petroleum
1-((4-Nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroquinoline (3p). It
was obtained in 81% yield (221.4 mg); light yellow solid; TLC
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
1
7.32−7.43 (m, 4H), 7.02 (dd, 2H, J = 8.2, 0.5 Hz), 6.88 (dd, 2H, J =
8.2, 2.0 Hz), 3.07 (s, 3H), 2.26 (s, 3H) ppm; 13C{1H} NMR (100
MHz, CDCl3): δ 139.2, 138.5, 137.6, 135.1, 129.6, 129.3, 21.0, 129.0,
126.5, 38.3 ppm; anal. calcd for C14H14ClNO2S: C 56.85, H 4.77, N
4.74, S 10.84. Found: C 56.93, H 4.73, N 4.79, S 10.76.
(petroleum ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz,
CDCl3): δ 8.26 (d, 2H, J = 9.0 Hz), 7.81 (d, 1H, J = 8.4 Hz), 7.77 (d,
2H, J = 9.0 Hz), 7.24 (d, 1H, J = 8.1 Hz), 7.15 (t, 1H, J = 7.6 Hz),
7.05 (d, 1H, J = 7.2 Hz), 3.88 (t, 2H, J = 6.0 Hz), 2.45 (t, 2H, J = 6.6
Hz), 1.63−1.71 (m, 2H) ppm; 13C{1H} NMR (100 MHz, CDCl3): δ
150.0, 145.2, 130.9, 129.4, 128.2, 126.9, 125.9, 125.0, 124.2, 46.9,
26.4, 21.8 ppm; anal. calcd for C15H14N2O4S: C 56.59, H 4.43, N
8.80, S 10.07. Found: C 56.65, H 4.48, N 8.69, S 9.98.
N-Methyl-4-nitro-N-phenylbenzenesulfonamide (3i). It was
obtained in 95% yield (277.7 mg); yellow solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
8.22 (dt, 2H, J = 9.0, 2.2 Hz), 7.65 (dt, 2H, J = 9.0, 2.2 Hz), 7.22−
7.28 (m, 3H), 6.98−7.03 (m, 2H), 3.16 (s, 3H) ppm; 13C{1H} NMR
(100 MHz, CDCl3): δ 150.1, 142.3, 140.6, 129.3, 129.0, 128.0, 126.6,
124.0, 38.4 ppm; anal. calcd for C13H12N2O4S: C 53.42, H 4.14, N
9.58, S 10.97. Found: C 53.44, H 4.13, N 9.61, S 11.03.
2-(Phenylsulfonyl)-1,2,3,4-tetrahydroisoquinoline (3q). It was
obtained in 72% yield (229.2 mg); white solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (300 MHz, CDCl3): δ
7.86 (dd, 2H, J = 3.6, 1.2 Hz), 7.56−7.60 (m, 3H), 7.14−7.18 (m,
2H), 7.05−7.10 (m, 2H), 4.29 (s, 2H), 3.38−3.41 (m, 2H), 2.95 (t,
2H, J = 4.2) ppm; 13C{1H} NMR (75 MHz, CDCl3): δ 136.4, 133.0,
132.8, 131.5, 129.1, 128.8, 127.7, 126.8, 126.4, 126.3, 47.5, 43.7, 28.8
ppm; anal. calcd for C15H15NO2S: C 65.91, H 5.53, N 5.12, S 11.73.
Found: C 65.99, H 5.57, N 5.06, S 11.62.
N-Methyl-4-nitro-N-(p-tolyl)benzenesulfonamide (3j). It was
obtained in 95% yield (291.0 mg); yellow solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
8.22 (d, 2H, J = 8.7 Hz), 7.66 (d, 2H, J = 8.7 Hz), 7.05 (d, 2H, J = 8.5
Hz), 6.87 (d, 2H, J = 8.5 Hz), 3.13 (s, 3H), 2.27 (s, 3H) ppm;
13C{1H} NMR (100 MHz, CDCl3): δ 150.1, 142.4, 138.1, 137.9,
129.9, 129.0, 126.4, 124.0, 38.5, 21.1 ppm; anal. calcd for
C14H14N2O4S: C 54.89, H 4.61, N 9.14, S 10.47. Found: C 54.92,
H 4.58, N 9.09, S 10.40.
2-((4-Nitrophenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline (3r).
It was obtained in 76% yield (241.9 mg); light yellow solid; TLC
1
(petroleum ether/ethyl acetate, 100:15 v/v); H NMR (300 MHz,
CDCl3): δ 8.37 (d, 2H, J = 7.8 Hz), 8.03 (d, 2H, J = 7.8 Hz), 8.03 (d,
2H, J = 7.8 Hz), 7.16−7.19 (m, 2H), 7.04−7.10 (m, 2H), 4.37 (s,
2H), 3.49 (t, 2H, J = 5.4 Hz), 2.94 (t, 2H, J = 5.4 Hz) ppm; 13C{1H}
NMR (75 MHz, CDCl3): δ 150.1, 143.0, 132.7, 130.9, 128.9, 128.7,
127.1, 126.6, 126.2, 124.3, 47.4, 43.7, 28.6 ppm; anal. calcd for
C15H14N2O4S: C 56.59, H 4.43, N 8.80, S 10.07. Found: C 56.73, H
4.41, N 8.78, S 9.97.
N-Methyl-2-nitro-N-phenylbenzenesulfonamide (3k). It was
obtained in 90% yield (263.1 mg); yellow solid; TLC (petroleum
1
ether/ethyl acetate, 100:15 v/v); H NMR (250 MHz, CDCl3): δ
7.13−7.18 (m, 2H), 6.95−7.01 (m, 3H), 6.61 (dd, 2H, J = 8.7, 2.2
Hz), 6.57 (dd, 2H, J = 9.0, 2.0 Hz), 2.85 (s, 3H) ppm; 13C{1H} NMR
(100 MHz, CDCl3): δ 141.5, 134.8, 132.0, 130.9, 129.2, 128.9, 128.8,
127.9, 126.7, 123.2, 38.3 ppm; anal. calcd for C13H12N2O4S: C 53.42,
H 4.14, N 9.58, S 10.97. Found: C 53.49, H 4.10, N 9.59, S 10.92.
N-(4-(N-Methyl-N-phenylsulfamoyl)phenyl)acetamide (3l). It
was obtained in 87% yield (264.8 mg); white solid; TLC (petroleum
N-Ethyl-N-phenylbenzenesulfonamide (3s). It was obtained in
87% yield (227.3 mg); white solid; TLC (petroleum ether/ethyl
acetate, 100:15 v/v); 1H NMR (250 MHz, CDCl3): δ 7.46−7.55 (m,
3H), 7.34−7.41 (m, 2H), 7.22−7.25 (m, 3H), 6.94−6.98 (m, 2H),
3.54 (q, 2H, J = 7.2 Hz), 1.00 (t, 3H, J = 7.2 Hz) ppm; 13C{1H} NMR
(100 MHz, CDCl3): δ 138.7, 132.5, 130.9, 129.0, 128.9, 128.7, 127.9,
127.6, 45.6, 14.0 ppm; anal. calcd for C14H15NO2S: C 64.34, H 5.79,
N 5.36, S 12.27. Found: C 64.41, H 5.73, N 5.28, S 12.19.
4-Tosylmorpholine (3t). It was obtained in 78% yield (188.2 mg);
1
ether/ethyl acetate, 100:50 v/v); H NMR (250 MHz, CDCl3): δ
7.53 (d, 2H, J = 8.7 Hz), 7.40 (dt, 2H, J = 8.7, 2.2 Hz), 7.18−7.23 (m,
3H), 6.99−7.03 (m, 2H), 3.10 (s, 3H), 2.14 (s, 3H), 2.11 (s, 1H)
ppm; 13C{1H} NMR (100 MHz, CDCl3/dimethyl sulfoxide
(DMSO)-d6): δ 169.4, 143.4, 141.3, 129.6, 128.6, 128.5, 127.1,
126.32, 118.6, 37.9, 24.2 ppm; anal. calcd for C15H16N2O3S: C 59.19,
H 5.30, N 9.2, S 10.53. Found: C 59.24, H 5.33, N 9.90, S 10.47.
N-(4-Methoxy-3-(N-methyl-N-phenylsulfamoyl)phenyl)-
acetamide (3m). It was obtained in 85% yield (284.2 mg); white
1
white solid; TLC (petroleum ether/ethyl acetate, 100:10 v/v); H
NMR (300 MHz, CDCl3): δ 7.64 (d, 2H, J = 4.5, Hz), 7.35 (d, 2H, J
= 4.5, Hz), 3.75 (s, 4H), 2.99 (s, 4H), 2.45 (s, 3H) ppm; 13C{1H}
NMR (75 MHz, CDCl3): δ 143.9, 132.1, 129.7, 127.9, 66.1, 46.0, 21.5
ppm; anal. calcd for C11H15NO3S: C 54.75, H 6.27, N 5.80, S 13.29.
Found: C 54.78, H 6.32, N 5.77, S 13.25.
4-((4-Nitrophenyl)sulfonyl)morpholine (3u). It was obtained in
80% yield (217.8 mg); white solid; TLC (petroleum ether/ethyl
acetate, 100:10 v/v); 1H NMR (300 MHz, CDCl3): δ 8.43 (d, 2H, J =
8.7, Hz), 7.97 (d, 2H, J = 8.7, Hz), 3.78 (t, 4H, J = 4.2, Hz), 3.07 (t,
4H, J = 4.2, Hz) ppm; 13C{1H} NMR (75 MHz, CDCl3): δ 150.3,
141.3, 129.0, 124.4, 66.0, 45.9 ppm; anal. calcd for C10H12N2O5S: C
1
solid; TLC (petroleum ether/ethyl acetate, 100:50 v/v); H NMR
(250 MHz, DMSO-d6): δ 10.01 (s, 1H), 7.87 (d, 1H, J = 2.7 Hz),
7.77 (dd, 1H, J = 8.8, 2.7 Hz), 7.23−7.30 (m, 2H), 7.11−7.18 (m,
4H), 3.73 (s, 3H), 3.26 (s, 3H), 1.96 (s, 3H) ppm; 13C{1H} NMR
(100 MHz, DMSO-d6): δ 168.4, 152.1, 141.1, 131.8, 128.8, 126.4,
125.9, 125.4, 125.3, 121.3, 113.1, 56.0, 38.5, 23.6 ppm; anal. calcd for
C16H18N2O4S: C 57.47, H 5.43, N 8.38, S 9.59. Found: C 57.49, H
5.44, N 8.37, S 9.55.
2128
J. Org. Chem. 2021, 86, 2117−2134