Pathogens 2021, 10, 464
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2-Benzylbenzo[d]isothiazol-3(2H)-one (5f): Yield 77% mp 87–89 C; 1H NMR (600 MHz,
CDCl3) : 8.05 (d, J = 7.8 Hz, 1 H), 7.56 (t, J = 7.8 Hz, 1 H), 7.38 (t, J = 7.2 Hz, 1 H), 7.46
(d, J = 7.8 Hz, 1 H), 5.04 (s, 2 H), 7.34–7.29 (m, 5 H); 13C NMR (150 MHz, CDCl3)
: 165.35
δ
δ
(C=O), 140.42 (C), 136.19 (C), 131.87 (CH), 128.86 (CH), 128.46 (CH), 128.31 (CH), 126.84
(CH), 125.53 (CH), 124.50 (C), 120.42 (CH), 47.59 (CH2); EI–MS m/z: 241 [100, (M+)], 136
(79), 91 (88).
2-(4-Butylphenyl)benzo[d]isothiazol-3(2H)-one (5g): Yield 92%, mp 168–172 ◦C; 1H
NMR (600MHz, CDCl3)
7.45 (d, J = 7.2 Hz, 1 H), 7.40 (d, J = 7.2 Hz, 2 H), 7.13 (d, J = 8.4 Hz, 2 H), 2.57 (t, J = 7.8 Hz
2 H), 1.57 (m, 2 H), 1.33 (m, 2 H), 0.91 (t, J = 7.2 Hz, 3 H); 13C NMR (150 MHz, CDCl3)
: 163.23 (C=O), 141.28 (C), 133.53 (C), 131.22 (C), 128.29 (CH), 127.86 (CH), 126.12 (CH),
δ: 7.76 (d, J = 8.4 Hz, 1 H), 7.31 (t, J = 7.2 Hz, 1 H), 7.55 (m, 1 H),
,
δ
124.75 (CH), 123.76 (CH), 119.26 (C), 119.03 (CH), 32.46 (CH2), 28.68 (CH2), 21.29 (CH2),
12.92 (CH3); EI–MS (EI) m/z: 283 [44, (M+)], 282 (77), 240 (100).
2-(2-Nitrophenyl)benzo[d]isothiazol-3(2H)-one (5h): Yield 78%, mp 199–200 ◦C; 1H
NMR (600 MHz, CDCl3)
δ
: 8.07 (d, J = 4.8 Hz, 2 H), 7.71 (m, 2 H), 7.63 (m, 1 H), 7.55 (m, 1 H),
: 164.65 (C=O), 146.84
7.53 (m, 1 H), 7.44 (t, J = 7.2, 1 H); 13C NMR (150 MHz, CDCl3)
δ
(C), 141.02 (C), 133.86 (CH), 132.91 (CH), 130.03 (CH), 129.71 (C), 129.33 (CH), 127.61 (CH),
126.13 (CH), 125.84 (CH), 122.97 (C), 120.35 (CH); EI–MS m/z: 272 [35, (M+)], 152 (100).
2-(4-Nitrophenyl)benzo[d]isothiazol-3(2H)-one (5i): Yield 82%, mp 126–129 ◦C; 1H
NMR (600 MHz, CDCl3)
(
δ
: 8.09 (d, J = 7.8 Hz, 1 H), 7.70 (m, 1 H), 7.46 (m, 1 H), 7.59
: 164.32
d, J = 7.8 Hz, 1 H), 8.02 (m, 2 H), 8.31 (m, 2 H); 13C NMR (150 MHz, CDCl3)
δ
(C=O), 133.36 (CH), 127.58 (CH), 126.41 (CH), 124.97 (CH), 124.51 (C), 122.90 (CH), 120.19
(CH); EI–MS m/z: 272 [100, (M+)], 271 (36), 242 (31).
2-(2-Methyl-4-nitrophenyl)benzo[d]isothiazol-3(2H)-one (5j): Yield 81%, mp 135–138 ◦C
;
1H NMR (600 MHz, CDCl3)
H), 7.48 (t, J = 7.2, 1 H), 7.46 (d, J = 8.4, 1 H), 8.10 (d, J = 8.4, 1 H), 8.23 (s, 1 H), 2.35 (s, 3 H);
13C NMR (150 MHz, CDCl3)
: 164.56 (C=O), 146.71 (C), 145.99 (C), 141.12 (C), 135.80 (C),
δ: 7.05 (d, J = 7.8 Hz, 1 H), 7.70 (t, J = 7.2, 1 H), 7.56 (d, J = 7.8, 1
δ
132.81 (CH), 132.08 (CH), 127.44 (CH), 126.20 (CH), 124.72 (CH), 124.17 (CH), 123.15 (CH),
120.46 (C), 18.62 (CH3); EI–MS m/z: 286 [78, (M+)], 270 (29), 269 (100).
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2-(4-Bromophenyl)benzo[d]isothiazol-3(2H) (5k): Yield 84%, mp 138–140 C; 1H NMR
(600 MHz, CDCl3) δ: 8.07 (d, J = 7.8 Hz, 1 H), 7.65 (t, J = 7.8, 1 H), 7.43 (t, J = 7.8, 1 H), 7.58
(m, 5 H); 13C NMR (150 MHz, CDCl3)
δ: 163.07 (C=O), 138.58 (C), 135.37 (C), 131.59 (CH),
131.42 (CH), 126.26 (CH), 124.98 (CH), 124.82 (CH), 123.61 (C), 119.31 (C), 119.11 (CH);
EI–MS m/z (%): 305 [62, (M+)], 307 (100), 306 (46), 304 (72), 226 (82).
2-(2-Hydroxyphenyl)benzo[d]isothiazol-3(2H)-one (5l): Yield 77%, mp 198–200 ◦C;
1H NMR (600 MHz, CDCl3)
δ: 8.11 (d, J = 7.8 Hz, 1 H), 7.48 (m, 1 H), 7.69 (m, 1 H), 7.61
(
d, J = 7.2, 1 H), 7.36 (dd, J = 7.9, 1 H), 7.24 (m, 1 H), 6.95 (m, 1 H), 7.01 (dd, J = 8.2, 1 H);
13C NMR (150 MHz, CDCl3)
δ
: 165.03 (C=O), 151.69 (C), 141.77 (C), 132.70 (CH), 129.56
(CH), 127.20 (CH), 126.23 (CH), 125.37 (CH), 123.89 (CH), 121.39 (C), 121.33 (CH), 120.09
(CH); EI–MS m/z: 243 [95, (M+)], 136 (100).
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2-(2-Chlorophenyl)benzo[d]isothiazol-3(2H)-one (5m): Yield 68%, mp 117–119 C;
1H NMR (600 MHz, CDCl3)
(
δ
: 8.10 (d, J = 7.8 Hz, 1 H), 7.66 (m, 1 H), 7.38 (m, 1 H), 7.57
d, J = 7.8 Hz, 1 H), 7.53 (dd, J = 5.4Hz, 1 H), 7.39 (m, 2 H), 7.42 (dd, J = 6.0Hz, 1 H); 13
C
NMR (150 MHz, CDCl3) δ: 163.80 (C=O), 140.36 (C), 133.08 (C), 132.66 (C), 131.45 (CH),
130.07 (CH), 129.72 (CH), 129.68 (CH), 126.80 (CH), 126.38 (CH), 124.73 (CH), 122.32 (C),
119.27 (CH); EI–MS m/z: 261 [69, (M+)], 226 (100).
2-(2,6-Dichlorophenyl)benzo[d]isothiazol-3(2H)-one (5n): Yield 92%, mp 188–190 ◦C;
1H NMR (600 MHz, CDCl3)
δ
: 8.12 (d, J = 7.8 Hz, 1 H), 7.68 (m, 1-H), 7.35 (t, J = 7.8 Hz, 1H),
7.59 (d, J = 7.8 Hz, 1 H), 7.45 (m, 3 H); 13C NMR (150 MHz, CDCl3)
δ
: 163.53 (C=O), 140.87
(C), 135.75 (CH), 131.65 (CH), 130.55 (C), 130.21 (CH), 127.92 (CH), 126.58 (CH), 124.67
(CH), 122.0 (C), 119.53 (CH); EI–MS m/z: 295 [53, (M+)], 260 (100).
2-(4-Methoxyphenyl)benzo[d]isothiazol-3(2H)-one (5o): Yield 89%, mp 146–148 ◦C;
1H NMR (600 MHz, CDCl3)
(
δ
: 8.07 (d, J = 7.8 Hz, 1 H), 7.63 (m, 1 H), 7.53 (m, 3 H), 7.41
t, J = 7.2 Hz, 1 H), 6.96 (d, J = 9.0 Hz, 2 H), 3.82 (s, 3 H); 13C NMR (150 MHz, CDCl3)
δ: