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Y. Zhang et al.
Paper
Synthesis
N-(Benzamidomethyl)-4-chlorobenzamide (3ac)
HRMS (ESI): m/z [M + H]+ calcd for C16H16ClN2O2: 303.0895; found:
303.0885.
White solid; yield: 234.1 mg (81%); mp 193–194 °C.
1H NMR (400 MHz, CDCl3): = 7.90 (t, J = 6.0 Hz, 1 H), 7.82–7.72 (m, 5
H), 7.52 (t, J = 6.0 Hz, 1 H), 7.44–7.33 (m, 4 H), 5.03 (t, J = 6.4 Hz, 2 H).
13C NMR (101 MHz, CDCl3): = 168.60, 167.51, 133.29, 132.13,
131.79, 128.86, 128.73, 128.65, 128.62, 127.23, 45.68.
HRMS (ESI): m/z [M + H]+ calcd for C15H14ClN2O2: 289.0738; found:
2-Chloro-N-[(4-methylbenzamido)methyl]benzamide (3bg)
White solid; yield: 215.1 mg (71%); mp 201–202 °C.
1H NMR (400 MHz, CDCl3): = 7.73 (d, J = 8.0 Hz, 2 H), 7.70–7.60 (m, 3
H), 7.45–7.32 (m, 3 H), 7.25 (d, J = 8.0 Hz, 2 H), 5.07 (t, J = 6.3 Hz, 2 H),
2.42 (s, 3 H).
13C NMR (101 MHz, CDCl3): = 168.50, 167.80, 142.43, 134.40,
131.46, 130.97, 130.59, 130.28, 129.73, 129.22, 127.26, 126.93, 45.50,
21.50.
289.0745.
N-(Benzamidomethyl)-3-methylbenzamide (3ad)
White solid; yield: 228.7 mg (85%); mp 176–177 °C.
HRMS (ESI): m/z [M + H]+ calcd for C16H16ClN2O2: 303.0895; found:
303.0881.
1H NMR (400 MHz, CDCl3): = 7.87 (d, J = 7.2 Hz, 2 H), 7.72 (br s, 2 H),
7.67 (s, 1 H), 7.64 (d, J = 7.2 Hz, 1 H), 7.56 (t, J = 7.2 Hz, 1 H), 7.47 (t, J =
7.2 Hz, 2 H), 7.36–7.34 (m, 2 H), 5.14–5.08 (m, 2 H), 2.41 (s, 3 H).
13C NMR (101 MHz, CDCl3): = 168.77, 168.59, 138.41, 133.47,
133.44, 132.70, 131.95, 128.56, 128.45, 127.95, 127.32, 124.34, 45.66,
21.30.
N-(Benzamidomethyl)pyridine-4-carboxamide (3ag)
White solid; yield: 215.0 mg (84%); mp 209–210 °C.
1H NMR (400 MHz, CDCl3): = 8.74 (d, J = 5.6 Hz, 1 H), 8.3 (br s, 1 H),
7.92–7.83 (m, 3 H), 7.80 (br s, 1 H), 7.72 (d, J = 5.6 Hz, 1 H), 7.60–7.42
(m, 4 H), 5.11 (t, J = 6.0 Hz, 2 H).
HRMS (ESI): m/z [M + H]+ calcd for C16H17N2O2: 269.1285; found:
269.1290.
13C NMR (101 MHz, DMSO-d6): = 166.91, 165.43, 150.68, 141.36,
134.27, 131.86, 128.74, 127.88, 121.85, 45.63.
HRMS (ESI): m/z [M + H]+ calcd for C14H14N3O2: 256.1081; found:
256.1046.
N-(Benzamidomethyl)-3-chlorobenzamide (3ae)
White solid; yield: 231.2 mg (80%); mp 203–204 °C.
1H NMR (400 MHz, CDCl3): = 7.97 (t, J = 5.6 Hz, 1 H), 7.86–7.79 (m, 4
H), 7.69 (dt, J = 8.4, 1.6 Hz, 1 H), 7.52 (tt, J = 7.2, 1.6 Hz, 1 H), 7.48–7.45
(m, 1 H), 7.42 (t, J = 8.0 Hz, 2 H), 7.34 (t, J = 8.0 Hz, 1 H), 5.05 (t, J = 6.3
Hz, 2 H).
N-(Benzamidomethyl)pyridine-2-carboxamide (3ah)
White solid; yield: 209.9 mg (82%); mp 159–160 °C.
1H NMR (400 MHz, DMSO-d6): = 9.26 (t, J = 5.5 Hz, 1 H), 9.11 (t, J =
5.6 Hz, 1 H), 8.65 (d, J = 4.4 Hz, 1 H), 8.09 (d, J = 7.6 Hz, 1 H), 8.00 (t, J =
7.6 Hz, 1 H), 7.94–7.90 (m, 2 H), 7.61 (m, 1 H), 7.56–7.43 (m, 3 H),
4.95–4.88 (m, 2 H).
13C NMR (101 MHz, CDCl3): = 168.60, 167.24, 135.23, 134.85,
133.29, 132.12, 132.02, 129.89, 128.65, 127.73, 127.24, 125.25, 45.72.
HRMS (ESI): m/z [M + H]+ calcd for C15H14ClN2O2: 289.0738; found:
289.0725.
13C NMR (101 MHz, DMSO-d6): = 167.39, 164.01, 149.78, 149.00,
138.38, 134.40, 134.02, 132.03, 128.79, 127.89, 122.46, 45.65.
HRMS (ESI): m/z [M + H]+ calcd for C14H14N3O2: 256.1081; found:
256.1076.
N-(Benzamidomethyl)-2-chlorobenzamide (3af)
White solid; yield: 208.1 mg (72%); mp 201–202 °C.
1H NMR (400 MHz, CDCl3): = 7.88–7.82 (m, 4 H), 7.64 (t, J = 7.2 Hz, 1
H), 7.54 (t, J = 7.2 Hz, 1 H), 7.48–7.42 (m, 3 H), 5.10 (m, 2 H).
13C NMR (101 MHz, CDCl3): = 168.53, 167.85, 134.35, 133.43,
131.96, 131.54, 130.32, 129.77, 128.59, 128.55, 127.29, 126.98, 45.56.
N-(Benzamidomethyl)thiophene-2-carboxamide (3ai)
White solid; yield: 196.5 mg (75%); mp 151–152 °C.
1H NMR (400 MHz, DMSO-d6): = 9.13 (ddt, J = 23.6, 17.3, 5.6 Hz, 2
H), 7.96–7.85 (m, 3 H), 7.78 (dt, J = 5.1, 1.5 Hz, 1 H), 7.56–7.51 (m, 1
H), 7.46 (dd, J = 8.2, 6.6 Hz, 2 H), 7.14 (dd, J = 5.0, 3.7 Hz, 1 H), 4.83 (tt,
J = 15.7, 5.7 Hz, 2 H).
13C NMR (101 MHz, DMSO-d6): = 166.92, 161.90, 139.98, 134.29,
131.87, 131.67, 129.18, 128.73, 128.45, 127.88, 44.95.
HRMS (ESI): m/z [M + H]+ calcd for C15H14N2O2: 289.0738; found:
289.0745.
N,N′-Methylenebis(4-methylbenzamide) (3bb)30,32
White solid; yield: 246.2 mg (87%); mp 224–225 °C.
1H NMR (400 MHz, CDCl3): = 7.90 (br s, 2 H), 7.76 (d, J = 8.0 Hz, 4 H),
7.23 (d, J = 8.0 Hz, 4 H), 5.08 (t, J = 6.0 Hz, 2 H), 2.42 (s, 6 H).
HRMS (ESI): m/z [M + H]+ calcd for C13H14N2O2S: 262.0770; found:
262.0758.
13C NMR (101 MHz, CDCl3): = 168.48, 142.40, 130.70, 129.21,
127.29, 45.62, 21.49.
MS (EI): m/z = 283 [M + H]+.
N-(Benzamidomethyl)naphthalene-2-carboxamide (3aj)
White solid; yield: 259.3 mg (85%); mp 175–176 °C.
1H NMR (400 MHz, DMSO-d6): = 9.25 (t, J = 5.6 Hz, 1 H), 9.15 (t, J =
5.7 Hz, 1 H), 8.60–8.53 (s, 1 H), 8.05–7.93 (m, 6 H), 7.65–7.45 (m, 5 H),
4.97 (t, J = 5.6 Hz, 2 H).
13C NMR (101 MHz, DMSO-d6): = 166.99, 134.68, 134.41, 132.56,
131.88, 131.74, 129.35, 128.73, 128.29, 128.14, 128.06, 127.91,
127.17, 124.75, 45.72.
4-Chloro-N-[(4-methylbenzamido)methyl]benzamide (3bc)
White solid; yield: 227.3 mg (75%); mp 240–241 °C.
1H NMR (400 MHz, CDCl3): = 7.92 (br s, 1 H), 7.80 (d, J = 8.0 Hz, 2 H),
7.79 (br s, 1 H), 7.74 (d, J = 8.0 Hz, 2 H), 7.42 (d, J = 7.2 Hz, 2 H), 7.26 (d,
J = 7.2 Hz, 2 H), 5.05 (t, J = 5.6 Hz, 2 H), 2.42 (s, 3 H).
13C NMR (101 MHz, CDCl3): = 168.53, 167.04, 142.69, 138.25,
131.86, 130.47, 129.31, 128.89, 128.71, 127.21, 45.65, 21.50.
HRMS (ESI): m/z [M + H]+ calcd for C19H17N2O2: 305.1285; found:
305.1276.
© 2019. Thieme. All rights reserved. Synthesis 2019, 51, A–G