J
Synthesis
T. Liu et al.
Paper
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C15H17NO S Na: 378.0440;
1
H NMR (400 MHz, CDCl ): δ = 2.43 (s, 3 H, ArCH ), 3.93 (s, 3 H,
5
2
3
3
found: 378.0441.
ArOCH ), 7.28–7.32 (m, 3 H, ArH), 7.49 (t, J = 8.0 Hz, 2 H, ArH), 7.59–
3
7
7
.62 (m, 1 H, ArH), 7.67 (m, 1 H, ArH), 7.70–7.72 (m, 3 H, ArH), 7.84–
.86 (m, 2 H, ArH).
N-(4-Methoxy-3-(phenylsulfonyl)phenyl)butane-1-sulfonamide
3bn)
13
(
C NMR (100 MHz, CDCl ): δ = 21.7, 62.6, 119.6, 121.2, 127.4, 128.2,
3
Yellow-white solid; yield: 34.5 mg (90%); mp 107–109 °C.
129.0, 130.0, 131.6, 133.8, 135.4, 136.9, 140.4, 144.7, 152.2.
1
+
H NMR (400 MHz, CDCl ): δ = 0.92 (t, J = 8.0 Hz, 3 H, CH CH ), 1.40–
HRMS (ESI-TOF): m/z [M + Na] calcd for C20
H18BrNO
5
S
2
Na: 517.9702;
3
2
3
1
3
7
.48 (m, 2 H, CH ), 1.78–1.86 (m, 2 H, CH ), 3.06–3.12 (m, 2 H, CH ),
found: 517.9705.
2
2
2
.75 (s, 3 H, ArOCH ), 6.90 (d, J = 8.0 Hz, 1 H, ArH), 7.15 (br, 1 H, NH),
3
.48–7.53 (m, 2 H, ArH), 7.58–7.61 (m, 2 H, ArH), 7.95–7.99 (m, 3 H,
N-(3-Iodo-4-methoxy-5-(phenylsulfonyl)phenyl)-4-methylben-
ArH).
zenesulfonamide (3bs)
13
C NMR (100 MHz, CDCl ): δ = 13.6, 21.5, 25.4, 51.6, 56.3, 113.8,
Yellow-white solid; yield: 48.2 mg (89%); mp 181–183 °C.
3
1
23.6, 128.5, 128.7, 129.4, 129.8, 130.0, 133.4, 140.7, 154.8.
1
H NMR (400 MHz, CDCl ): δ = 2.42 (s, 3 H, ArCH ), 3.94 (s, 3 H,
3
3
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C17H21NO S Na: 406.0753;
ArOCH ), 7.27–7.29 (m, 2 H, ArH), 7.47–7.50 (m, 3 H, ArH), 7.59 (t, J =
5
2
3
found: 406.0750.
8.0 Hz, 1 H, ArH), 7.71 (d, J = 8.0 Hz, 2 H, ArH), 7.75 (d, J = 4.0 Hz, 1 H,
ArH), 7.83–7.85 (m, 2 H, ArH), 7.89 (d, J = 4.0 Hz, 1 H, ArH).
13
N-(4-Methoxy-3-(phenylsulfonyl)phenyl)-1-phenylmethanesul-
C NMR (100 MHz, CDCl ): δ = 21.7, 63.2, 93.8, 122.3, 127.4, 128.2,
3
fonamide (3bo)
129.0, 130.0, 133.7, 134.3, 135.4, 136.0, 140.4, 144.6, 154.8.
Yellow-white solid; yield: 37.1 mg (89%); mp 128–130 °C.
+
HRMS (ESI-TOF): m/z [M + Na] calcd for C20H18INO S Na: 565.9563;
found: 565.9565.
5
2
1
H NMR (400 MHz, CDCl ): δ = 3.75 (s, 3 H, ArOCH ), 4.34 (s, 2 H, CH ),
3
3
2
6.79 (br, 1 H, NH), 6.85 (d, J = 8.0 Hz, 1 H, ArH), 7.33–7.38 (m, 5 H,
ArH), 7.44–7.47 (m, 1 H, ArH), 7.51 (t, J = 8.0 Hz, 2 H, ArH), 7.60 (t, J =
N-(4-Methoxy-3-(phenylsulfonyl)naphthalen-1-yl)-4-methylben-
8.0 Hz, 1 H, ArH), 7.84 (m, 1 H, ArH), 7.96–7.97 (m, 2 H, ArH).
zenesulfonamide (3bt)
13
C NMR (100 MHz, CDCl ): δ = 56.3, 58.2, 113.7, 123.3, 128.3, 128.5,
Yellow-white solid; yield: 28.0 mg (60%); mp 185–187 °C.
3
1
28.7, 129.0, 129.1, 129.4, 129.5, 129.7, 130.9, 133.4, 140.7, 154.6.
1
H NMR (400 MHz, CDCl ): δ = 2.46 (s, 3 H, ArCH ), 4.12 (s, 3 H,
3
3
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C20H19NO S Na: 440.0597;
ArOCH ), 6.62 (br, 1 H, NH), 7.31 (d, J = 8.0 Hz, 2 H, ArH), 7.48 (t, J = 8.0
5
2
3
found: 440.0594.
Hz, 2 H, ArH), 7.56–7.61 (m, 3 H, ArH), 7.66–7.68 (m, 3 H, ArH), 7.88
(d, J = 8.0 Hz, 2 H, ArH), 8.07 (d, J = 12.0 Hz, 1 H, ArH), 8.24 (d, J = 8.0
Hz, 1 H, ArH).
N-(4-Methoxy-2-methyl-5-(phenylsulfonyl)phenyl)-4-methylben-
zenesulfonamide (3bp)
13
C NMR (100 MHz, CDCl ): δ = 21.8, 65.1, 122.1, 123.8, 124.2, 127.8,
3
Yellow-white solid; yield: 35.3 mg (82%); mp 118–120 °C.
127.9, 128.1, 128.9, 129.2, 129.9, 130.0, 133.5, 141.8, 144.6, 155.8.
1
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C24
H NMR (400 MHz, CDCl ): δ = 2.29 (s, 3 H, ArCH ), 2.46 (s, 3 H,
H21NO S Na: 490.0753;
5 2
3
3
ArCH ), 3.74 (s, 3 H, ArOCH ), 6.28 (br, 1 H, NH), 6.70 (s, 1 H, ArH),
found: 490.0756.
3
3
7.31 (d, J = 8.0 Hz, 2 H, ArH), 7.46–7.49 (m, 2 H, ArH), 7.51 (s, 1 H,
ArH), 7.56–7.59 (m, 1 H, ArH), 7.63 (d, J = 8.0 Hz, 2 H, ArH), 7.81–7.83
N-(4-Ethoxy-3-(phenylsulfonyl)phenyl)-4-methylbenzenesulfon-
(m, 2 H, ArH).
amide (3bu)
13
C NMR (100 MHz, CDCl ): δ = 19.0, 21.7, 56.1, 114.8, 126.8, 126.9,
Yellow-white solid; yield: 40.5 mg (94%); mp 154–156 °C.
3
1
1
27.6, 128.3, 128.5, 128.6, 129.9, 133.1, 136.0, 141.2, 144.3, 144.9,
55.7.
1
H NMR (400 MHz, CDCl ): δ = 1.28 (t, J = 12.0 Hz, 3 H, CH CH ), 3.69
3
2
3
(s, 3 H, ArCH ), 3.93 (q, J = 12.0 Hz, 2 H, CH CH ), 6.80 (d, J = 12.0 Hz, 1
3
2
3
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C21H21NO S Na: 454.0753;
H, ArH), 6.90 (br, 1 H, NH), 7.24–7.27 (m, 2 H, ArH), 7.45–7.51 (m, 3 H,
5
2
found: 454.0755.
ArH), 7.57–7.63 (m, 4 H, ArH), 7.84 (d, J = 8.0 Hz, 2 H, ArH).
13
C NMR (100 MHz, CDCl ): δ = 14.3, 21.7, 65.0, 113.9, 124.7, 127.4,
3
N-(3-Fluoro-4-methoxy-5-(phenylsulfonyl)phenyl)-4-methylben-
zenesulfonamide (3bq)
128.5, 128.6, 128.8, 129.0, 129.8, 131.2, 133.2, 135.5, 140.7, 144.2,
154.5.
Yellow-white solid; yield: 38.3 mg (88%); mp 176–178 °C.
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C21H21NO S Na: 454.0753;
found: 454.0755.
5
2
1
H NMR (400 MHz, CDCl ): δ = 2.43 (s, 3 H, ArCH ), 3.94 (s, 3 H,
3
3
ArOCH ), 7.20 (br, 1 H, NH), 7.29 (d, J = 8.0 Hz, 2 H, ArH), 7.49 (t, J = 8.0
3
Hz, 2 H, ArH), 7.59–7.62 (m, 1 H, ArH), 7.66 (m, 1 H, ArH), 7.69–7.71
N-(4-Isopropoxy-3-(phenylsulfonyl)phenyl)-4-methylbenzenesul-
(m, 3 H, ArH), 7.85 (d, J = 8.0 Hz, 2 H, ArH).
fonamide (3bv)
13
C NMR (100 MHz, CDCl ): δ = 21.7, 62.6, 119.6, 121.3, 127.4, 128.2,
Yellow-white solid; yield: 39.6 mg (89%); mp 168–170 °C.
3
1
29.0, 130.1, 131.6, 133.7, 133.8, 135.4, 136.9, 140.5, 144.7, 152.2.
1
H NMR (400 MHz, CDCl ): δ = 1.12 (s, 3 H, CHCH ), 1.13 (s, 3 H,
3
3
+
HRMS (ESI-TOF): m/z [M + Na] calcd for C20H18FNO S Na: 458.0503;
CHCH ), 2.43 (s, 3 H, ArCH ), 4.47–4.53 (m, 1 H, CHCH ), 6.81 (d, J = 8.0
5
2
3
3
3
found: 458.0500.
Hz, 1 H, ArH), 7.26–7.28 (m, 3 H, ArH), 7.45–7.53 (m, 3 H, ArH), 7.56–
7.61 (m, 4 H, ArH), 7.81 (d, J = 8.0 Hz, 2 H, ArH).
13
N-(3-Bromo-4-methoxy-5-(phenylsulfonyl)phenyl)-4-methylben-
C NMR (100 MHz, CDCl ): δ = 21.3, 21.7, 71.5, 114.7, 125.0, 127.4,
3
zenesulfonamide (3br)
128.4, 128.5, 128.6, 129.4, 129.8, 131.3, 133.1, 135.6, 141.0, 144.2,
153.6.
Yellow-white solid; yield: 42.0 mg (85%); mp 160–162 °C.
©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–L