Page 7 of 10
Journal Name
RSC Advances
DOI: 10.1039/C4RA12944J
110.6, 55.8, 55.6. ESI-HRMS (m/z)
C19H17NO2S (M + Na): 346.0878, found (M + Na): 346.0876.
:
Calculated for 2H), 7.94 (s, 1H), 7.469 (d,
J
= 1.8 Hz, 1H), 7.33 (dd, J1 = 8.3
Hz, J2 = 1.9 Hz , 1H), 6.81 (d,
MHz, DMSOꢀ d6): δ (ppm) 198.1, 149.6, 144.7, 142.0, 133.1,
130.2 (q, = 32.9 Hz), 124.3, 123.17 (q, = 271 Hz), 119.6,
118.7, 116.2, 114.6; ESI-HRMS (m/z) Calculated for
C14H12BrNOS (M + Na): 343.9721, found (M + Na): 343.9721.
J
= 8.3 Hz, 1H); 13C NMR (100
J
J
3,4-Dimethoxy-N-(4-methoxyphenyl)benzothioamide
(3eb).28 Yellow solid; Yield ꢀ 93% (282 mg); mp: 164ꢀ165 ºC
(lit.29 154ꢀ155 oC); Rf (30% EtOAc/hexane) 0.25; IR (KBr, cmꢀ
1): 3163, 1514, 1270, 1146. 1H NMR (400 MHz, DMSOꢀ d6): δ
:
(ppm), 11.40 (brs, 1H), 7.64 (d,
J = 8.6 Hz, 2H), 7.54 (s, 2H),
N
-Cyclohexyl-3,4-dimethoxybenzothioamide
(3jb).
7.03 (d, = 9.0 Hz, 1H), 7.99 (d,
J
J = 8.7 Hz, 2H), 3.83 (s, 6H), Yellow solid; Yield ꢀ 96% (268 mg); mp: 162ꢀ164 ºC; Rf (20%
3.78 (s, 3H); 13C NMR (100 MHz, DMSOꢀ d6): δ (ppm) 195.8, EtOAc/hexane) 0.25; IR (KBr, cmꢀ1): 3228, 3193, 2936, 2854,
157.2, 151.3, 147.7, 134.3, 133.2, 126.2, 120.8, 113.5,111.3, 1541, 1510, 1268, 1242, 1144, 1021. 1H NMR (400 MHz,
110.5, 55.7, 55.5, 55.3. ESI-HRMS (m/z): Calculated for DMSOꢀ d6): δ (ppm), 9.78 ꢀ 9.77 (m, NH, 1H), 7.38ꢀ7.35 (m,
C16H17NO3S (M + Na): 326.0827, found (M + Na): 326.0823.
2H), 6.97 (d, J = 8.8 Hz, 1H), 4.44ꢀ4.37 (m, CHNH, 1H), 3.80
(s, 6H), 1.98ꢀ1.96 (m, 2H); 1.78ꢀ1.75 (m, 2H), 1.65ꢀ1.62 (m,
1H), 1.45ꢀ1.27 (m, 4H), 1.19ꢀ1.11 (m, 1H); 13C NMR (100
MHz, DMSOꢀ d6): δ (ppm) 194.7, 151.0, 147.6, 133.8, 120.3,
111.6, 110.4, 55.7, 55.5, 55.0, 30.7, 25.1, 24.8; ESI-HRMS
(m/z): Calculated for C15H21NO2S (M + Na): 302.1191, found
(M + Na): 302.1194.
N
-(3,5-bis(Trifluoromethyl)phenyl)-3,4-
dimethoxybenzothioamide (3fb). Yellow solid; Yield ꢀ 98%
(400 mg); mp: 159ꢀ161 ºC. Rf (20% EtOAc/hexane) 0.3; IR
(KBr, cmꢀ1) 3289, 1512, 1377, 1279, 1263, 1164, 1130. 1H
NMR (400 MHz, DMSOꢀ d6): δ (ppm), 11.89 (brs, 1H), 8.63
(s, 2H), 7.99 (s, 1H), 7.61ꢀ7.58 (m, 2H), 7.08 (d,
1H), 3.853 (s, 3H) 3.847 (s, 3H); 13C NMR (100 MHz, DMSOꢀ
d6): δ (ppm) 197.9, 152.0, 147.8, 141.9, 134.1, 130.3 (q,
32.8 Hz), 124.5, 123.6 (q,
J = 8.4 Hz,
N
-Cyclohexyl-4-hydroxy-3,5-dimethylbenzothioamide
J
=
(3jd).22b Yellow solid; Yield ꢀ 80% (210 mg); mp: 212ꢀ214 ºC
o
J
= 278.9 Hz), 121.3, 119.0, 111.4, (lit.22b 222ꢀ224 C); Rf (20% EtOAc/hexane) 0.25; IR (KBr,
110.7, 55.8, 55.6; ESI-HRMS (m/z): Calculated for C17H13 cmꢀ1): 3249, 3054, 2933, 1547, 1393, 1324, 1209, 1178. 1H
F6NO2S (M + H): 410.0649, found (M + H): 410.0659.
NMR (400 MHz, DMSOꢀ d6): δ (ppm), 9.63ꢀ9.62 (m, NH, 1H),
8.75 (brs, OH, 1H), 7.39 (s, 2H), 4.38 (brs, CHNH, 1H), 2.19
(s, 6H), 1.95ꢀ1.93 (m, 2H); 1.77ꢀ1.74 (m, 2H), 1.65ꢀ1.62 (m,
1H), 1.40ꢀ1.27 (m, 4H), 1.15ꢀ1.12 (m, 1H); 13C NMR (100
MHz, DMSOꢀ d6): δ (ppm) 195.1, 155.8, 132.2, 127.9, 123.1,
54.8, 30.7, 25.2, 24.8, 16.6;. ESI-HRMS (m/z): Calculated for
C15H21 NOS (M + Na): 286.1242, found (M + H): 286.1245.
N
-(4-Chlorophenyl)-4-methoxybenzothioamide
(3ga).
Yellow solid; Yield ꢀ 79% (220 mg); mp: 186ꢀ187 ºC; Rf (20%
EtOAc/hexane) 0.4; IR (KBr, cmꢀ1): 3149, 2973, 1601, 1504,
1488, 1305, 1246, 1175, 837. 1H NMR (400 MHz, DMSOꢀ d6):
δ (ppm), 11.47 (brs, 1H), 7.90 (d,
J
= 8.3 Hz, 2H), 7.65 (d,
J =
7.7 Hz, 2H), 7.22 (d, = 7.5 Hz, 2H), 7.00 (d,
J
J
= 8.2 Hz, 2H),
3.83 (s, 3H), 2.32 (s, 3H); 13C NMR (100 MHz, DMSOꢀ d6): δ
N
-Phenylthiophene-2-carbothioamide (5aa).22a Yellow
(ppm) 196.76, 161.79, 139.12, 134.43, 129.84, 129.57, 128.39, solid; Yield ꢀ 89% (195 mg); mp: 94ꢀ97 ºC (lit.22a 94ꢀ95 C); Rf
o
126.12, 113.23, 55.52; ESI-HRMS (m/z): Calculated for (10% EtOAc/hexane) 0.2; IR (KBr, cmꢀ1): 3294, 1544, 1375,
C14H12ClNOS (M + H): 278.0406, found (M + Na): 278.0404.
1350, 1172. 1H NMR (400 MHz, DMSOꢀ d6): δ (ppm), 11.54
(brs, 1H), 7.88 (brs, 1H), 7.85 (d,
J = 5.0 Hz, 1H), 7.67 (d, J =
7.8 Hz, 2H), 7.44 (t,
J = 7.7 Hz, 2H), 7.28 (t, J = 7.3 Hz, 1H),
4-Methoxy-N-(3-nitrophenyl)benzothioamide
(3ha).
7.23ꢀ7.21 (m, 1H); 13C NMR (100 MHz, DMSOꢀ d6): δ (ppm)
Yellow solid; Yield ꢀ 83% (119 mg); mp: 152ꢀ154 ºC; Rf (20%
EtOAc/hexane) 0.3; IR (KBr, cmꢀ1): 3345, 1602, 1521, 1345,
1259. 1H NMR (400 MHz, DMSOꢀ d6): δ (ppm), 11.60 (brs,
186.7, 148.2, 139.4, 134.8, 128.5, 128.2, 126.4, 125.1, 125.0.
ESI-HRMS (m/z)
: Calculated for C11H9NS2 (M + H):
220.0255, found (M + Na): 220.025.
1H), 7.89 (d,
= 8.3 Hz, 2H), 7.01 (d,
NMR (100 MHz, DMSOꢀ d6): δ (ppm) 197.5, 162.0, 147.5,
J
= 8.2 Hz, 2H), 7.82 (d,
J = 8.0 Hz, 2H), 7.48 (d,
J
J
= 8.4 Hz, 2H), 3.83 (s, 3H); 13C
5-Methyl-N-phenylthiophene-2-carbothioamide
(5ab).
141.2, 134.3, 130.5, 129.8, 129.7, 120.5, 118.6, 113.3, 55.6. Yellow solid; Yield ꢀ 91% (212 mg); mp: 123ꢀ125 ºC Rf (20%
ESI-HRMS (m/z): Calculated for C14H12N2O3S (M + Na): EtOAc/hexane) 0.5; IR (KBr, cmꢀ1): 1517, 1446, 1335; 1H
311.0466, found (M + Na): 311.0467.
NMR (400 MHz, DMSOꢀ d6): δ (ppm), 11.39 (brs, 1H), 7.71
(d, = 2.3 Hz, 1H), 7.66 (d, = 7.8 Hz, 2H), 7.43 (t, = 7.7
Hz, 2H), 7.27 (t, = 7.3 Hz, 1H), 6.92 (d, = 2.8 Hz, 1H), 2.46
J
J
J
J
J
4-Methoxy-N-(4-nitrophenyl)benzothioamide
(3ia).
(s, 3H); 13C NMR (100 MHz, DMSOꢀ d6): δ (ppm) 186.5,
149.2, 145.7, 139.5, 128.5, 126.9, 126.2, 125.2, 125.1, 15.4.
ESI-HRMS (m/z): Calculated for C12H11NS2 (M + Na):
256.0231, found (M + Na): 256.0238.
Yellow solid; Yield ꢀ 85% (122 mg); mp: 191ꢀ193 ºC; Rf (20%
EtOAc/hexane) 0.2; IR (KBr, cmꢀ1): 3134, 1596, 1506, 1340,
1305, 1252, 1171. 1H NMR (400 MHz, DMSOꢀ d6): δ (ppm),
11.19 (brs, 1H), 8.29 (d,
2H), 7.89 (d, = 7.6 Hz, 2H), 7.03 (d,
3H); 13C NMR (100 MHz, DMSOꢀ d6): δ (ppm) 197.9, 162.1,
J
= 8.0 Hz, 2H), 8.18 (d,
J = 7.8 Hz,
= 7.6 Hz, 2H), 3.84 (s,
J
J
4-Methyl-N-phenylthiophene-2-carbothioamide
(5ac).
146.1, 143.9, 134.7, 129.8, 124.2, 123.9, 113.3, 55.6. ESI- Yellow solid; Yield ꢀ 53% (123 mg); mp: 93ꢀ95 ºC (lit.22c 70ꢀ71
HRMS (m/z)
:
Calculated for C14H12N2O3S (M
+
Na): oC in CCl4); Rf (20% EtOAc / hexane) 0.3; IR (KBr, cmꢀ1):
311.0466, found (M + Na): 311.0464.
3189, 1506, 1206, 714, 696. 1H NMR (400 MHz, DMSOꢀ d6):
δ (ppm), 11.48 (brs, 1H), 7.79 (s, 2H), 7.63 (d,
J
= 5 Hz, 1H),
7.42 (t,
J
= 7.5 Hz, 2H), 7.26 (t,
J
= 7.2 Hz, 1H), 6.965 (d, = 4
J
N
-(3,5-bis(Trifluoromethyl)phenyl)-3,4-
Hz, 1H), 2.38 (s, 3H); 13C NMR (100 MHz, DMSOꢀ d6): δ
(ppm) 189.2, 142.4, 139.7, 135.3, 131.1, 128.9, 128.6, 126.2,
123.6, 15.4; ESI-HRMS (m/z): Calculated for C12H11NS2 (M +
Na): 256.0231, found (M + H): 256.0233.
dihydroxybenzothioamide (3fe). Yellow solid; Yieldꢀ99%
(189 mg); Rf (40% EtOAc/hexane) 0.3; IR (KBr, cmꢀ1): 3307,
1608, 1515, 1381, 1277. 1H NMR (400 MHz, DMSOꢀ d6): δ
(ppm) 11.76 (brs, 1H), 9.79 (brs, 1H), 9.37 (brs, 1H), 8.62 (s,
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