10.1002/ejoc.201801393
European Journal of Organic Chemistry
FULL PAPER
Spectral Data:
5-(trifluoromethyl)benzo[d]thiazol-2(3H)-one 2f
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
374mg, 85% yield. Mp: 222-223 °C; 1H NMR (500 MHz, DMSO-
d6, 25°C): δ (ppm) = 12.23 (brs, 1H, NH), 7.85 (d, 1H, J =8.5 Hz,
CHarom), 7.48 (d, 1H, J=8.0 Hz, CHarom), 7.33 (s, 1H,
CHarom); 13C NMR (125 MHz, DMSO-d6, 25°C): δ (ppm) =
169.75, 136.75, 128.42 (d, 1C, J =1.25 Hz), 126.94 (q, 1C, J
=32.5 Hz), 124.04 (q, 1C, J =270.0 Hz), 123.78, 119.00 (q, 1C, J
=3.8 Hz), 107.60 (q, 1C, J =3.8 Hz) ; 19F NMR (500 MHz,
DMSO-d6, 25°C): δ (ppm) = -60.77 (brs, 3F). IR (ATR): ṽ= 3676,
2991, 1689, 1640, 1333, 1164, 1148, 1115, 1154, 887, 771 cm-1.
HRMS (ESI): calcd for C8H5ONF3S [M + H]+: 220.00385; found:
220.00325.
Benzothiazolone 2a
This is a known compound. 2,2′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
285 mg, 94% yield. Mp: 138-140 °C; MS (EI): m/z 151.0
[C7H5NOS], calcd [M] 151.0. 1H NMR (500 MHz, CDCl3, 25℃): δ
(ppm) = 9.85 (brs, 1 H, NH), 7.41 (d, 1H, J =7 Hz, CHarom),
7.30-7.26 (m, 1 H, CHarom), 7.17-7.14 (m, 2 H, CHarom).; 13C
NMR (125 MHz, CDCl3, 25°C): δ (ppm) = 172.81, 135.26,
126.51, 123.92, 123.27, 122.56, 111.67. IR (ATR): ṽ= 3310,
3155, 3105, 2884, 1659, 1465, 1218, 1123, 736, 701 cm-1. The
NMR spectra are in agreement with previously reported data[18a]
.
6-chlorobenzo[d]thiazol-2(3H)-one 2b
This is a known compound. 2,2′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
297 mg, 80% yield. Mp: 213-215 °C; MS (EI): m/z 185.0
[C7H4ClNOS], calcd [M] 185.1. 1H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) = 12.02 (brs, 1H, NH), 7.75 (s, 1H, CHarom),
7.32 (d, 1H, J =8.5, CHarom), 7.10 (d, 1H, J =8.5 Hz, CHarom);
13C NMR, (125 MHz, DMSO-d6, 25°C): δ (ppm) = 169.73, 135.24,
126.43, 125.15, 122.36, 122.70. IR (ATR): ṽ= 3676, 2989, 2902,
1671, 1597, 1466, 1210, 1054, 812, 800, 716, 651, 566 cm-1.
The NMR spectra are in agreement with previously reported
6-(methylsulfonyl)benzo[d]thiazol-2(3H)-one 2g
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1),, yield:
299mg, 65% yield. Mp: 242-243 °C; 1H NMR (500 MHz, DMSO-
d6, 25°C): δ (ppm) = 11.73 (brs, 1H,NH), 7.36 (s, 1H, CHarom),
7.08 (d, 1H, J = 8.5 Hz, CHarom), 7.00 (d, 1H, J = 8.0 Hz,
CHarom), 2.30 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6,
25°C): δ (ppm) = 170.26, 140.44, 134.74, 125.71, 124.30,
122.25, 111.59, 43.95. IR (ATR): ṽ= 3667, 2989, 2902, 1693,
1405, 1291, 1261, 1143, 1131, 1098, 1077, 1061, 784 cm-1.
HRMS (ESI): calcd for C8H8O3NS2 [M + H]+: 229.99401; found:
229.99358.
.
6-bromobenzo[d]thiazol-2(3H)-one 2c
This is a known compound. 2,2′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
413mg, 90% yield. Mp: 230-232 °C; MS (EI): m/z 228.9
[C7H4BrNOS], calcd [M] 228.9. 1H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) = 12.03 (brs, 1H,NH), 7.86 (d, 1H, J = 2.0 Hz,
CHarom), 7.44 (dd, 1H, J1 =8.5, J2 =2.0 Hz, CHarom), 7.06 (d,
1H, J = 8.5 Hz, CHarom); 13C NMR (125 MHz, DMSO-d6, 25°C):
δ (ppm) = 169.66, 135.60, 129.18, 125.56, 125.02, 113.96,
113.13. IR (ATR): ṽ= 3134, 3009, 1668, 1597, 1460, 1209, 809,
713, 647, 540 cm-1. The NMR spectra are in agreement with
5-benzoylbenzo[d]thiazol-2(3H)-one 2h
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
432mg, 85% yield. Mp: 192-194 °C; MS (EI): m/z 255.95
[C14H9NO2S], calcd [M] 255.3. 1H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) 12.09 (brs, 1 H, NH), 7.78-7.75 (m, 3 H,
CHarom), 7.70-7.67 (m, 1 H, CHarom), 7.57 (t, 2 H, J =2.5 Hz,
CHarom) , 7.51-7.49 (m, 1 H, CHarom), 7.44 (d, J = 1.5 Hz, 1 H,
CHarom); 13C NMR (125 MHz, DMSO-d6, 25°C): δ (ppm) =
194.92, 169.67, 137.08, 136.43, 134.96, 132.60, 129.51, 128.97,
128.55, 124.09, 122.80, 112.19. IR (ATR): ṽ= 3673, 2973, 2902,
1718, 1649, 1604, 1285, 1069, 701 cm-1. The NMR spectra are
previously reported data[29]
.
5-chlorobenzo[d]thiazol-2(3H)-one 2d
in agreement with previously reported data[31]
.
This is a known compound[30]. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
324mg, 87% yield. Mp: 238-239 °C; MS (EI): m/z 185.0
[C7H4ClNOS], calcd [M] 184.9. 1H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) = 12.04 (brs, 1H,NH), 7.61 (dd, 1H, J1 =8.5, J2
=1.5, CHarom ), 7.19 (dd, 1H, J1 =8.5, J2 =2.5 Hz, CHarom),
7.12 (d, 1H, J =2.0 Hz, CHarom); 13C NMR (125 MHz, DMSO-d6,
25°C): δ (ppm) = 170.07, 137.45, 130.79, 124.25, 122.42,
122.19, 111.20. IR (ATR): ṽ= 3666, 2989, 2902, 1672, 1577,
1408, 1302, 1078, 843, 793, 746, 718, 648, 578 cm-1.
4-methylbenzo[d]thiazol-2(3H)-one 2i
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
281mg, 85% yield. Mp: 210-212 °C; 1H NMR (500 MHz, DMSO-
d6, 25°C): δ (ppm) = 11.73 (brs, 1H, NH), 7.37 (d, 1H, J =7.5Hz,
CHarom), 7.09 (d, 1H, J =7.5Hz, CHarom), 7.03 (t, 1H, J =7.5
Hz, CHarom), 2.32 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6,
25°C): δ (ppm) = 170.42, 135.03, 127.57, 122.84, 122.47,
121.30, 119.98, 17.44. IR (ATR): ṽ= 3679, 2988, 2902, 1665,
1408, 1381, 1074 cm-1. HRMS (ESI): calcd for C8H8ONS [M +
H]+: 166.03211; found: 166.03181.
4-fluorobenzo[d]thiazol-2(3H)-one 2e
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
294mg, 87% yield. Mp: 173-175 °C; MS (EI): m/z 169.0
[C7H4FNOS], calcd [M] 169.0. 1H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) = 12.40 (brs, 1H, NH), 7.42 (d, 1H, J =7.5 Hz,
CHarom), 7.12-7.22 (m, 2H, CHarom); 13C NMR (125 MHz,
DMSO-d6, 25°C): δ (ppm) = 169.77, 147.18 (d, 1C, J =243.8 Hz),
125.64 (d, 1C, J =3.8 Hz), 124.40 (d, 1C, J =15.0 Hz), 123.14 (d,
1C, J =6.3 Hz), 118.73 (d, 1C, J =3.8 Hz), 112.79 (d, 1C, J =16.3
Hz) ; 19F NMR (500 MHz, DMSO-d6, 25°C): δ (ppm) = -128.46
(brs, 1F). IR (ATR): ṽ= 3673, 2989, 2902, 1670, 1631, 1485,
1394, 1200, 1076, 1066, 1053, 764, 702 cm-1. The NMR spectra
6-methoxybenzo[d]thiazol-2(3H)-one 2j
This is a known compound. 6,6′-Disulfanediyldianiline reacted
with COS under the general procedure to produce a white solid.
The crude product was eluted by EA and CH2Cl2 (20:1), yield:
336mg, 93% yield. Mp: 160-161 °C; MS (EI): m/z 181.0
1
[C8H7NO2S], calcd [M] 180.9. H NMR (500 MHz, DMSO-d6,
25°C): δ (ppm) = 11.66 (brs, 1H), 7.23 (d, 1H, J =2.5 Hz,
CHarom), 7.02 (d, 1H, J =9.0 Hz, CHarom), 6.86 (dd, 1H, J1 =
8.5 Hz, J2 =2.5 Hz, CHarom), 3.73 (s, 3H, OCH3); 13C NMR (125
MHz, DMSO-d6, 25°C): δ (ppm) = 169.74, 155.22, 129.87,
124.32, 113.22, 112.10, 107.74, 55.59. IR (ATR): ṽ= 3667, 2989,
2902, 1670, 1409, 1063, 791 cm-1. The NMR spectra are in
are in agreement with previously reported data[28, 31]
.
agreement with previously reported data[28]
.
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