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L. J. Gooßen et al.
PRACTICAL SYNTHETIC PROCEDURES
13C NMR (151 MHz, CDCl3): d = 163.7, 133.8, 131.9, 128.7, 126.7,
121.5, 118.7, 32.6, 30.9.
MS (EI, 70 eV): m/z (%) = 203 (5, [M]+), 188 (49), 146 (7), 105
(100), 77 (40), 51 (11).
1H NMR (600 MHz, CDCl3): d = 8.24 (d, J = 10.0 Hz, 1 H), 7.72–
7.75 (m, 2 H), 7.51–7.55 (m, 1 H), 7.45 (t, J = 7.7 Hz, 2 H), 7.29–
7.33 (m, 2 H), 7.17 (dd, J = 11.0, 9.7 Hz, 1 H), 7.09–7.13 (m, 2 H),
5.84 (d, J = 9.5 Hz, 1 H).
13C NMR (151 MHz, CDCl3): d = 163.3 (d, J = 301 Hz, C-F),
160.7, 133.2, 132.2, 131.7 (d, J = 2.8 Hz), 129.5 (d, J = 8.4 Hz),
128.8, 127.0, 122.4, 116.2 (d, J = 22.2 Hz), 109.9.
Anal. Calcd for C13H17NO: C, 76.81; H, 8.43; N, 6.89. Found: C,
76.49; H, 8.46; N, 6.72.
N-[(Z)-4-Phenylbut-1-en-1-yl]benzamide (3c)
MS (EI, 70 eV): m/z (%) = 241 (56, [M]+), 135 (3), 109 (6), 105
Synthesized following Method A from benzamide (121.1 mg, 1.00
mmol) and 4-phenylbut-1-yne (281 mL, 2.00 mmol) and purified by
column chromatography (EtOAc–hexane, 1:9), yielding the product
as a white solid (231.2 mg, 92%).
(100), 77 (37), 51 (12).
Anal. Calcd for C15H12FNO: C, 74.68; H, 5.01; N, 5.81. Found: C,
74.42; H, 4.98; N, 5.68.
1H NMR (600 MHz, CDCl3): d = 7.61 (d, J = 7.2 Hz, 2 H), 7.51 (t,
J = 7.4 Hz, 1 H), 7.41 (t, J = 7.8 Hz, 2 H), 7.26–7.30 (m, 3 H), 7.22–
7.25 (m, 2 H), 7.16 (t, J = 7.3 Hz, 1 H), 6.89 (dd, J = 10.6, 9.1 Hz,
1 H), 4.94 (q, J = 7.9 Hz, 1 H), 2.76 (t, J = 7.3 Hz, 2 H), 2.39–2.44
(m, 2 H).
2-Methyl-N-[(Z)-2-phenylvinyl]acrylamide (3g)
Synthesized following Method A from 2-methylacrylamide (85.1
mg, 1.00 mmol) and phenylacetylene (220 mL, 2.00 mmol) and pu-
rified by column chromatography (EtOAc–hexane, 1:9), yielding
the product as a yellowish oil (168.5 mg, 90%).
13C NMR (151 MHz, CDCl3): d = 164.3, 141.5, 133.7, 131.8,
128.53, 128.50, 128.4, 127.0, 126.2, 122.1, 110.9, 35.4, 28.3.
MS (EI, 70 eV): m/z (%) = 251 (4, [M]+), 160 (47), 105 (100), 91
(27), 77 (37), 51 (11).
1H NMR (600 MHz, CDCl3): d = 8.06 (d, J = 7.4 Hz, 1 H), 7.39 (t,
J = 7.8 Hz, 2 H), 7.28 (d, J = 7.2 Hz, 2 H), 7.24 (t, J = 7.4 Hz, 1 H),
7.03 (dd, J = 11.1, 9.6 Hz, 1 H), 5.80 (d, J = 9.7 Hz, 1 H), 5.72 (s, 1
H), 5.43 (d, J = 1.0 Hz, 1 H), 1.97 (s, 3 H).
13C NMR (151 MHz, CDCl3): d = 165.1, 139.2, 135.7, 129.1, 127.7,
126.9, 122.1, 121.0, 110.5, 18.4.
Anal. Calcd for C17H17NO: C, 81.24; H, 6.82; N, 5.57. Found: C,
81.37; H, 6.78; N, 5.69.
MS (EI, 70 eV): m/z (%) = 187 (100, [M]+), 159 (85), 144 (25), 117
N-[(Z)-5-Chloropent-1-en-1-yl]benzamide (3d)
(24), 69 (77), 41 (58).
Synthesized following Method A from benzamide (121.1 mg, 1.00
mmol) and 5-chloropent-1-yne (210 mL, 2.00 mmol) and purified by
column chromatography (EtOAc–hexane, 1:9), yielding the product
as a white solid (203.6 mg, 91%).
1H NMR (600 MHz, CDCl3): d = 7.95 (d, J = 9.0 Hz, 1 H), 7.80–
7.84 (m, 2 H), 7.51 (t, J = 7.4 Hz, 1 H), 7.44 (t, J = 7.6 Hz, 2 H),
7.01 (dd, J = 10.6, 9.2 Hz, 1 H), 4.78 (q, J = 8.3 Hz, 1 H), 3.61–3.64
(m, 2 H), 2.29–2.34 (m, 2 H), 1.91 (dq, J = 6.5, 6.3 Hz, 2 H).
Anal. Calcd for C12H13NO: C, 76.98; H, 7.00; N, 7.48. Found: C,
76.81; H, 7.02; N, 7.15.
2-Acetamido-N-[(Z)-2-phenylvinyl]acetamide (3h)
Synthesized following Method A from 2-acetamido-acetamide
(116.1 mg, 1.00 mmol) and phenylacetylene (220 mL, 2.00 mmol)
and purified by column chromatography (EtOAc–hexane, 1:9),
yielding the product as a white solid (209.5 mg, 96%).
13C NMR (151 MHz, CDCl3): d = 164.5, 133.6, 131.9, 128.7, 127.1,
123.3, 109.4, 44.5, 31.3, 22.3.
MS (EI, 70 eV): m/z (%) = 223 (18, [M]+), 188 (7), 160 (7), 105
(100), 77 (29), 51 (10).
1H NMR (400 MHz, CDCl3): d = 8.49 (d, J = 10.6 Hz, 1 H), 7.36 (t,
J = 7.5 Hz, 2 H), 7.21–7.28 (m, 3 H), 6.83 (dd, J = 11.1, 9.7 Hz, 1
H), 6.62 (s, 1 H), 5.76 (d, J = 9.9 Hz, 1 H), 3.96 (s, 2 H), 1.96 (s, 3
H).
13C NMR (101 MHz, CDCl3): d = 170.9, 166.9, 135.1, 128.9, 128.0,
127.1, 121.0, 111.4, 43.6, 22.7.
Anal. Calcd for C12H14ClNO: C, 64.43; H, 6.31; N, 6.26. Found: C,
64.10; H, 6.21; N, 5.98.
MS (EI, 70 eV): m/z (%) = 218 (9, [M]+), 119 (100), 104 (4), 91
N-[(Z)-2-(4-Methoxyphenyl)vinyl]benzamide (3e)
(10), 65 (4), 43 (11).
Synthesized following Method A from benzamide (121.1 mg, 1.00
mmol) and 4-methoxyphenylacetylene (259 mL, 2.00 mmol) and
purified by column chromatography (EtOAc–hexane, 1:8), yielding
the product as a white solid (210.3 mg, 83%).
1H NMR (600 MHz, CDCl3): d = 8.30 (d, J = 10.2 Hz, 1 H), 7.75 (d,
J = 7.4 Hz, 2 H), 7.52 (t, J = 7.3 Hz, 1 H), 7.44 (t, J = 7.7 Hz, 2 H),
7.27 (d, J = 8.4 Hz, 2 H), 7.12 (t, J = 10.2 Hz, 1 H), 6.95 (d, J = 8.4
Hz, 2 H), 5.83 (d, J = 9.2 Hz, 1 H), 3.82 (s, 3 H).
Anal. Calcd for C12H14N2O2: C, 66.04; H, 6.47; N, 12.84. Found: C,
66.32; H, 6.57; N, 12.61.
3-Nitro-N-[(Z)-2-phenylvinyl]benzamide (3i)
Synthesized following Method A from 3-nitrobenzamide (168.2
mg, 1.00 mmol) and phenylacetylene (220 mL, 2.00 mmol) and pu-
rified by column chromatography (EtOAc–hexane, 1:9), yielding
the product as a white solid (214.6 mg, 80%).
13C NMR (151 MHz, CDCl3): d = 164.2, 158.5, 133.4, 132.0, 129.0,
128.8, 128.0, 127.0, 121.3, 114.6, 110.7, 55.3.
MS (EI, 70 eV): m/z (%) = 253 (64, [M]+), 150 (12), 133 (8), 105
(100), 77 (45), 51 (15).
1H NMR (600 MHz, CDCl3): d = 8.58 (d, J = 10.8 Hz, 1 H), 8.54 (s,
1 H), 8.30 (d, J = 8.2 Hz, 1 H), 8.04 (d, J = 7.9 Hz, 1 H), 7.62 (t,
J = 7.9 Hz, 1 H), 7.37 (t, J = 7.9 Hz, 2 H), 7.32 (d, J = 7.2 Hz, 2 H),
7.22 (t, J = 7.4 Hz, 1 H), 7.08 (t, J = 10.5 Hz, 1 H), 5.92 (d, J = 9.5
Hz, 1 H).
13C NMR (151 MHz, CDCl3): d = 162.1, 148.0, 135.1, 134.8, 132.7,
129.8, 129.1, 127.8, 127.2, 126.3, 122.2, 121.7, 112.5.
Anal. Calcd for C16H15NO2: C, 75.87; H, 5.97; N, 5.53. Found: C,
75.59; H, 5.82; N, 5.31.
N-[(Z)-2-(4-Fluorophenyl)vinyl]benzamide (3f)
MS (EI, 70 eV): m/z (%) = 268 (64, [M]+), 150 (100), 120 (20), 104
Synthesized following Method A from benzamide (121.1 mg, 1.00
mmol) and 1-ethynyl-4-fluorobenzene (229 mL, 2.00 mmol) and pu-
rified by column chromatography (EtOAc–hexane, 1:9), yielding
the product as a white solid (238.9 mg, 99%).
(36), 76 (25), 50 (13).
Anal. Calcd for C15H12N2O3: C, 67.16; H, 4.51; N, 10.44. Found: C,
67.15; H, 4.68; N, 10.52.
Synthesis 2009, No. 13, 2283–2288 © Thieme Stuttgart · New York