The Journal of Organic Chemistry
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yield). Mp: 198−200 °C. Rf (6:4 hexane/ethyl acetate) = 0.5. IR
(ATR): 3373, 3203, 16942, 1652, 1384, 1370,1290, 1243, 1198, 1039,
979, 872 cm−1. 1H NMR (400 MHz, DMSO): δ 8.11 (d, J = 1.7 Hz,
1H), 8.02 (s, 1H), 7.88 (d, J = 16.0 Hz, 1H), 7.66 (dd, J = 8.3, 1.8 Hz,
2H), 7.42 (d, J = 8.2 Hz, 1H), 6.70 (d, J = 16.0 Hz, 1H), 4.19 (q, J =
7.1 Hz, 2H), 1.25 (t, J = 7.1 Hz, 3H). 13C{1H} NMR (100 MHz,
DMSO): δ 169.2, 165.9, 140.4, 136.9, 133.9, 132.4, 129.6, 129.4,
123.2, 120.9, 60.2, 14.2. HRMS (ESI-TOF): m/z calcd for
C12H12BrNNaO3 [M + Na]+, 319.9893; found, 319.9889.
6.04 (s, 1H), 5.87 (s, 1H), 4.24 (q, J = 7.1 Hz, 2H), 3.85 (s, 3H), 1.31
(t, J = 7.1 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3): δ 166.8,
160.7, 141.2, 137.5, 128.8, 125.1, 118.9, 116.7, 112.8, 60.5, 55.6, 14.3.
HRMS (ESI-TOF): m/z calcd for C13H16NO4 [M + H]+, 250.1074;
found, 250.1082.
(E)-Methyl 3-(2-Carbamoyl-4-methylphenyl)acrylate (4m). Fol-
lowing GP-A, the title compound was isolated as a white solid (30 mg,
55% yield). Mp: 195−197 °C. Rf (6:4 hexane/ethyl acetate) = 0.5. IR
(ATR): 3399, 3192, 1702, 1643, 1393, 1273, 1242, 11175, 1018, 832
1
cm−1. H NMR (400 MHz, DMSO): δ 7.94 (d, J = 16.1 Hz, 2H),
(E)-Ethyl 3-(2-Carbamoyl-5-(trifluoromethyl)phenyl)acrylate
(4g). Following GP-A, the title compound was isolated as a white
solid (31 mg, 43% yield). Mp: 188−190 °C. Rf (6:4 hexane/ethyl
acetate) = 0.5. IR (ATR): 3374, 3203, 1694, 1657, 1321, 1276, 1177,
7.78 (d, J = 8.4 Hz, 1H), 7.56 (s, 1H), 7.29 (d, J = 7.5 Hz, 2H), 6.54
(d, J = 16.0 Hz, 1H), 3.71 (s, 3H), 2.35 (s, 3H). 13C{1H} NMR (100
MHz, DMSO): δ 170.2, 166.7, 143.0, 142.2, 139.9, 138.1, 130.4,
128.7, 128.1, 126.7, 117.9, 51.5, 20.8. HRMS (ESI-TOF): m/z calcd
for C12H14NO4 [M + H]+, 220.0968; found, 220.0960.
1
1133, 1040 cm−1. H NMR (400 MHz, DMSO): δ 8.19−8.17 (m,
2H), 7.85−7.81 (m, 3H), 7.67 (d, J = 8.0 Hz, 1H), 6.84 (d, J = 16.0
Hz, 1H), 4.20 (q, J = 7.1 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H). 13C{1H}
NMR (100 MHz, DMSO): δ 169.1, 165.0, 141.6, 140.1, 139.6, 131.0
(E)-4-Methoxy-2-(2-(phenylsulfonyl)vinyl)benzamide (4n). Fol-
lowing GP-A, the title compound was isolated as a white solid (48
mg, 63% yield). Mp: 175−177 °C. Rf (5:5 hexane/ethyl acetate) =
0.3. IR (ATR): 3450, 3159, 1668, 1597, 1392, 1296, 1246, 1139,
(q, 1JC−F = 271 Hz), 130.2 (q, 2JC−F = 32 Hz), 128.5, 126.3 (q, 3JC−F
3.8 Hz), 125.0, 124.8, 123.8 (q, JC−F = 3.8 Hz), 121.6, 60.3, 14.1.
HRMS (ESI-TOF): m/z calcd for C13H13F3NO3 [M + H]+,
288.0848; found, 288.0851.
=
3
1
1083, 1027, 833 cm−1. H NMR (400 MHz, DMSO): δ 8.12 (d, J =
15.4 Hz, 1H), 7.93 (d, J = 7.5 Hz, 3H), 7.78−7.59 (m, 5H), 7.55−
7.51 (m, 1H), 7.36 (d, J = 2.2 Hz, 1H), 7.07−7.03 (m, 1H), 3.82 (s,
3H). 13C{1H} NMR (100 MHz, DMSO): δ 169.4, 160.3, 140.6,
140.3, 133.7, 132.3, 130.2, 129.8, 129.6, 129.0, 127.7, 127.2, 116.6,
111.9, 55.7. HRMS (ESI-TOF): m/z calcd for C16H16NO4S [M +
H]+, 318.0795; found, 318.0793.
(E)-Ethyl 3-(2-Carbamoyl-5-nitrophenyl)acrylate (4h). Following
GP-A, the title compound was isolated as a white solid (20 mg, 30%
yield). Mp: 189−191 °C. Rf (6:4 hexane/ethyl acetate) = 0.5. IR
(ATR): 3351, 3210, 1679, 1518, 1353, 1285, 1212, 1178, 1040 cm−1.
1H NMR (400 MHz, DMSO): δ 8.64 (d, J = 2.0 Hz, 1H), 8.30−8.20
(m, 2H), 7.93−7.84 (m, 2H), 7.72 (d, J = 8.4 Hz, 1H), 6.85 (d, J =
16.0 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 1.26 (t, J = 7.1 Hz, 3H). 13C
NMR (100 MHz, DMSO): δ 168.6, 166.2, 165.7, 149.1, 148.2, 143.3,
140.0, 139.63, 133.1, 129.1, 128.9, 124.2, 123.5, 122.4, 121.8, 60.4,
14.2. HRMS (ESI-TOF): m/z calcd for C12H13N2O5 [M + H]+,
265.0819; found, 265.0827.
2-(2-(Phenylsulfonyl)vinyl)-4-(trifluoromethyl)benzamide (E/Z =
7:1) (4o). Following GP-A, the title compound was isolated as a white
solid (69 mg, 75% yield). Mp: 215−217 °C. Rf (5:5 hexane/ethyl
acetate) = 0.4. IR (ATR): 3367, 3168, 1661, 1609, 1330, 1308, 1280,
1
1124, 1080, 850 cm-1. E isomer- H NMR (400 MHz, DMSO): δ
8.25 (d, J = 18.1 Hz, 2H), 7.97−7.84 (m, 7H), 7.73 (m, 6H). Z
isomer- 1H NMR (400 MHz, DMSO) 8.15 (d, J = 14.5 Hz, 0.27 H),
7.63−7.52 (m, 0.48). 13C{1H} NMR (100 MHz, DMSO): δ 168.7,
141.8, 140.1, 137.6, 132.5 (q, 1J C−F = 271 Hz), 130.8, 130.3 (q, 2JC−F
= 32 Hz), 129.6 (q, 2JC−F = 26 Hz), 128.9, 127.7, 127.1 (q, 3JC−F = 2.8
Hz), 124.9, 124.4 (q, 3JC−F = 3.4 Hz). HRMS (ESI-TOF): m/z calcd
for C16H12F3NNaO3S [M + Na]+, 378.0382; found, 378.0391.
(E)-4-(2-(Phenylsulfonyl)vinyl)benzo[d][1,3]dioxole-5-carboxa-
mide (4p). Following GP-A, the title compound was isolated as a
white solid (55 mg, 67% yield). Mp: 201−203 °C. Rf (5:5 hexane/
ethyl acetate) = 0.4. IR (ATR): 3401, 3204, 2887, 1656, 1454, 1445,
1296, 1254, 1142, 1067, 923, 830 cm−1. 1H NMR (400 MHz,
DMSO): δ 8.01 (d, J = 15.6 Hz, 1H), 7.97−7.88 (m, 2H), 7.73 (d, J =
7.3 Hz, 1H), 7.66 (t, J = 7.5 Hz, 2H), 7.52 (s, 2H), 7.25 (d, J = 15.6
Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 7.03 (d, J = 8.0 Hz, 1H), 6.17 (s,
2H). 13C{1H} NMR (101 MHz, DMSO): δ 169.1, 148.7, 147.2,
140.4, 135.3, 133.8, 130.9, 130.7, 129.8, 127.2, 122.3, 112.8, 109.4,
102.5. HRMS (ESI-TOF): m/z calcd for C16H13NNaO5S [M + Na]+,
354.0407; found, 354.0411.
(E)-Methyl 3-(2-Carbamoyl-5-methylphenyl)acrylate (4i). Fol-
lowing GP-A, the title compound was isolated as a white solid (33
mg, 60% yield). Mp: 206−208 °C. Rf (6:4 hexane/ethyl acetate) =
0.5. IR (ATR): 3373, 3194, 1695, 1655, 1389, 1301, 1226, 1034, 871
1
cm−1. H NMR (400 MHz, CDCl3): δ 8.13 (d, J = 16.0 Hz, 1H),
7.51−7.43 (m, 2H), 7.23 (d, J = 7.8 Hz, 1H), 6.39 (d, J = 16.0 Hz,
1H), 5.82 (s, 2H), 3.80 (s, 3H), 2.40 (s, 3H). 13C{1H} NMR (100
MHz, DMSO): δ 170.0, 166.6, 142.5, 139.5, 135.0, 131.7, 130.4,
127.7, 127.2, 118.6, 51.5, 20.7. HRMS (ESI-TOF): m/z calcd for
C12H14NO3 [M + H]+, 220.0968; found, 220.0976.
(E)-Methyl 3-(2-Carbamoyl-5-fluorophenyl)acrylate (4j). Follow-
ing GP-A, the title compound was isolated as a white solid (31 mg,
57% yield). Mp: 189−191 °C. Rf (6:4 hexane/ethyl acetate) = 0.5. IR
(ATR): 3389, 3204, 1697, 1652, 1392, 1304, 1217, 1034, 976 cm−1
.
1H NMR (400 MHz, DMSO): δ 8.03−7.90 (m, 2H), 7.79 (dd, J =
10.4, 2.5 Hz, 1H), 7.65−7.50 (m, 2H), 7.31 (td, J = 8.5, 2.5 Hz, 1H),
6.70 (d, J = 16.0 Hz, 1H), 3.73 (s, 3H). 13C{1H} NMR (100 MHz,
DMSO): δ 169.2, 166.4, 162.5(d, 1JC−F = 245.0 Hz), 141.0(d, 4JC−F
=
2.0 Hz), 134.43, 130.2(d, 3JC−F = 9 Hz), 120.5, 116.7(d, 2JC−F = 21.7
Hz), 113.4(d, 2JC−F = 22.7 Hz), 51.65. HRMS (ESI-TOF): m/z calcd
for C11H11FNO3 [M + H]+, 224.0717; found, 224.0712.
3,5-Dimethoxy-2-(2-(phenylsulfonyl)vinyl)benzamide (E/Z = 2:1)
(4q). Following GP-A, the title compound was isolated as a white
solid (56 mg, 74% yield). Mp: 215−217 °C. Rf (5:5 hexane/ethyl
acetate) = 0.4. IR (ATR): 3395, 3206, 1652, 1600, 1388, 1300, 1282,
1140, 1081, 973,861 cm−1. E-Isomer 1H NMR (400 MHz, DMSO): δ
8.02 (s, 1H), 7.95−7.62 (m, 13H),7.27 (d, J = 15.4 Hz, 1H), 6.70
(E)-Ethyl 3-(2-Carbamoyl-4-methylphenyl)acrylate (4k). Follow-
ing GP-A, the title compound was isolated as a white solid (32 mg,
55% yield). Mp: 177−179 °C. Rf (6:4 hexane/ethyl acetate) = 0.5. IR
(ATR): 3380, 3209, 1688, 1652, 1385, 1301, 1278, 1043, 978, 832
1
(br.s, 1H), 6.64 (br.s, 1H), 3.90 (s, 3H), 3.86 (s, 3H). Z-Isomer H
1
cm−1. H NMR (400 MHz, DMSO): δ 7.93 (d, J = 16.0 Hz, 2H),
NMR (400 MHz, DMSO): δ 7.43 (s, 0.51H), 6.55 (s, 0.65H), 6.50
(s, 0.57H), 3.75 (s, 1.91H), 3.66 (s, 1.87H). 13C{1H} NMR (100
MHz, DMSO): δ 170.4, 169., 162.1, 161.0, 158.9, 158.2, 142.9, 141.3,
138.9, 138.7, 136.0, 133.8, 133.3, 129.6, 129.4, 127.7, 127.2, 126.9,
115.0, 110.1, 105.1, 103.7, 99.3, 99.1, 56.2, 55.8, 55.8, 55.3, 54.6, 20.5.
HRMS (ESI-TOF): m/z calcd for C17H18NO5S [M + H]+, 348.0900;
found, 348.0901.
7.78 (d, J = 8.1 Hz, 1H), 7.56 (s, 1H), 7.28 (d, J = 7.6 Hz, 2H), 6.53
(d, J = 16.0 Hz, 1H), 4.18 (q, J = 7.1 Hz, 2H), 2.35 (s, 3H), 1.24 (t, J
= 7.1 Hz, 3H). 13C{1H} NMR (100 MHz, DMSO): δ 170.2, 166.3,
142.0, 139.9, 138.1, 130.4, 128.7, 128.1, 126.8, 118.3, 60.0, 20.8, 14.2.
HRMS (ESI-TOF): m/z calcd for C13H16NO3 [M + H]+, 234.1125;
found, 234.1129.
5-Methyl-2-(2-(phenylsulfonyl)vinyl)benzamide (E/Z = 8:1) (4r).
Following GP-A, the title compound was isolated as a white solid (56
mg, 74% yield). Mp: 215−217 °C. Rf (5:5 hexane/ethyl acetate) =
0.4. IR (ATR): 3395, 3206, 1652, 1600, 1388, 1300, 1282,, 1140,
1081, 973,861 cm−1. E-Isomer 1H NMR (400 MHz, DMSO): δ
8.02−7.93 (m, 2H), 7.90 (d, J = 7.4 Hz, 2H), 7.69 (m, 5H), 7.51 (d, J
(E)-Ethyl 3-(2-Carbamoyl-4-methoxyphenyl)acrylate (4l). Follow-
ing GP-A, the title compound was isolated as a white solid (26 mg,
42% yield). Mp: 178−180 °C. Rf (6:4 hexane/ethyl acetate) = 0.3. IR
(ATR): 3380, 3209, 1688, 1652, 1385, 1301, 1278, 1043, 978, 832
cm−1. 1H NMR (400 MHz, CDCl3): δ 8.01 (d, J = 15.9 Hz, 1H), 7.60
(d, J = 8.7 Hz, 1H), 7.11−6.92 (m, 2H), 6.31 (d, J = 15.9 Hz, 1H),
9751
J. Org. Chem. 2021, 86, 9744−9754