6140
A. Shaabani et al. / Tetrahedron Letters 48 (2007) 6137–6141
3
3JHH = 7.2 Hz, H-Ar), 7.60 (2H, d, JHH = 7.2 Hz,
H-Ar). 13C NMR (75 MHz, D2O): dC (ppm) 20.38
(CH3), 23.68, 24.16, 30.21 (5CH2 of cyclohexyl), 50.22
(CH–N of cyclohexyl), 128.76, 128.90, 133.03, 142.04
(C-Ar), 175.53 (C@O). Anal. Calcd for C14H19NO: C,
77.38; H, 8.81; N, 6.45. Found: C, 77.20; H, 8.75; N,
6.50.
H-Ar), 8.39 (1H, s, H-Ar). 13C NMR (75 MHz, D2O):
dC (ppm) 35.57 (N–CH2–CH2–NH), 52.36 (CH2–N–
CH2), 54.11 (N–CH2–CH2–NH), 66.05 (CH2–O–CH2),
123.45, 125.49, 129.38, 135.01, 137.86, 147.54 (C-Ar),
172.62 (C@O). Anal. Calcd for C13H17N3O4: C,
55.91; H, 6.14; N, 15.05. Found: C, 55.79; H, 6.27; N,
14.93.
2.4. N-tert-Butyl-3-nitrobenzamide (3f)
2.8. N-(2,4,4-Trimethylpentan-2-yl)-3-nitrobenzamide (3j)
White powder (0.19 g, yield 86%); mp 228–230 °C. IR
(KBr) (mmax/cmꢀ1): 3340, 2917, 2820, 1639, 1527, 1346.
MS (EI, 70 eV) m/z (%): 167 (MH2þꢀC4H9, 35), 150
White powder (0.26 g, yield 92%); mp 205–207 °C. IR
(KBr) (mmax/cmꢀ1): 3435, 2914, 1643, 1543, 1377. MS
(EI, 70 eV) m/z (%): 167 (MH2þꢀC8H17, 20), 150 (2),
1
1
(10), 121 (25), 74 (15), 65 (65), 58 (100), 43 (20). H
121 (20), 100 (100), 65 (55), 56 (40), 42 (25). H NMR
NMR (300 MHz, D2O, NH exchanged): dH (ppm)
1.21 (9H, s, C(CH3)3), 7.49–8.44 (4H, m, H-Ar). 13C
NMR (75 MHz, D2O): dC (ppm) 27.39 (C(CH3)3),
53.85 (C(CH3)3), 125.11, 128.23, 129.92, 131.06,
135.84, 148.26 (C-Ar), 169.16 (C@O). Anal. Calcd for
C11H14N2O3: C, 59.45; H, 6.35; N, 12.60. Found: C,
59.20; H, 6.41; N, 12.67.
(300 MHz, DMSO-d6): dH (ppm) 0.94 (9H, s,
C(CH3)3), 1.73 (6H, s, C(CH3)2), 1.64 (2H, s, CH2),
3
7.61 (1H, t, JHH = 7.5 Hz, H-Ar), 8.20 (1H, d,
3
3JHH = 7.7 Hz, H-Ar), 8.29 (1H, d, JHH = 7.1 Hz, H-
Ar), 8.47 (1H, br s, NH), 8.64 (1H, s, H-Ar). 13C
NMR (75 MHz, DMSO-d6): dC (ppm) 27.22
(C(CH3)2), 31.29 (CH2), 31.51 (C(CH3)3), 52.57
(C(CH3)3), 54.94 (C(CH3)2), 123.72, 124.31, 129.51,
135.68, 141.96, 147.88 (C-Ar), 167.58 (C@O). Anal.
Calcd for C15H22N2O3: C, 64.73; H, 7.97; N, 10.06.
Found: C, 64.65; H, 7.82; N, 9.98.
2.5. N-tert-Butyl-3-chlorobenzamide (3g)
White powder (0.19 g, yield 90%); mp 223–225 °C. IR
(KBr) (mmax/cmꢀ1): 3445, 2924, 1644, 1546, 1367. MS
(EI, 70 eV) m/z (%): 156 (MH2þꢀC4H9, 55), 139 (65),
111 (30), 75 (25), 58 (100), 41 (20). 1H NMR
(300 MHz, D2O, NH exchanged): dH (ppm) 1.19 (9H,
2.9. (E)-(Cyclohexylimino)methyl 3-nitrobenzoate 4
White powder (0.26 g, yield 95%); mp 70–72 °C. IR
(KBr) (mmax/cmꢀ1): 3341, 2941, 2859, 1687, 1598, 1535.
MS (EI, 70 eV) m/z (%): 276 (M+, 20), 167 (35), 150
3
s, C(CH3)3), 7.27 (1H, t, JHH = 7.7 Hz, H-Ar), 7.37
(1H, d, 3JHH = 7.7 Hz, H-Ar), 7.60 (1H, d,
3JHH = 7.5 Hz, H-Ar), 7.67 (1H, s, H-Ar). 13C NMR
(75 MHz, D2O): dC (ppm) 26.48 (C(CH3)3), 51.78
(C(CH3)3), 126.95, 128.58, 129.66, 130.84, 133.45,
138.10 (C-Ar), 174.10 (C@O). Anal. Calcd for
C11H14ClNO: C, 62.41; H, 6.67; N, 6.62. Found: C,
62.30; H, 6.72; N, 6.53.
1
(13), 121 (15), 74 (25), 65 (60), 58 (100), 43 (25). H
NMR (300 MHz, DMSO-d6): dH (ppm) 1.12–1.72
(10H, m, 5CH2 of cyclohexyl), 3.58 (1H, m, CH–N of
3
cyclohexyl), 7.80 (1H, t, JHH = 7.8 Hz, H-Ar), 7.91
3
(1H, s, CH=N), 8.33 (1H, d, JHH = 7.4 Hz, H-Ar),
3
8.45 (1H, d, JHH = 7.9 Hz, H-Ar), 8.60 (1H, s, H-Ar).
13C NMR (75 MHz, DMSO-d6): dC (ppm) 24.79,
25.58, 32.75 (5CH2 of cyclohexyl), 46.48 (CH–N of
cyclohexyl), 124.26, 127.72, 130.95, 133.02, 135.82,
148.30 (C-Ar), 160.38 (CH@N), 166.00 (C@O). Anal.
Calcd for C14H16N2O4: C, 60.86; H, 5.84; N, 10.14.
Found: C, 60.76; H, 5.73; N, 10.23.
2.6. N-tert-Butylbenzamide (3h)
White powder (0.15 g, yield 85%); mp 223–224 °C. IR
(KBr) (mmax/cmꢀ1): 3445, 2924, 1638, 1521, 1384. MS
(EI, 70 eV) m/z (%): 122 (MH2þꢀC4H9, 50), 105 (65),
77 (60), 58 (100), 43 (20). 1H NMR (300 MHz,
DMSO-d6): dH (ppm) 1.26 (9H, s, C(CH3)3), 7.30–7.88
(5H, m, H-Ar), 8.50 (1H, br s, NH). 13C NMR
(75 MHz, DMSO-d6): dC (ppm) 26.45 (C(CH3)3), 53.26
(C(CH3)3), 128.52, 129.18, 130.21, 133.89 (C-Ar),
171.68 (C@O). Anal. Calcd for C11H15NO: C, 74.54;
H, 8.53; N, 7.90. Found: C, 74.49; H, 8.61; N, 7.82.
Acknowledgements
We gratefully acknowledge financial support from the
Research Council of Shahid Beheshti University.
2.7. N-(2-Morpholinoethyl)-3-nitrobenzamide (3i)
References and notes
White powder (0.25 g, yield 91%); mp 203–205 °C. IR
(KBr) (mmax/cmꢀ1): 3430, 2939, 2864, 1642, 1526, 1347.
MS (EI, 70 eV) m/z (%): 167 (MH2þꢀC6H12NO, 25),
1. North, M. Contemp. Org. Synth. 1994, 1, 475–494.
2. (a) Beckwith, A. L. J. In The Chemistry of Amides:
Synthesis of Amides; Zabicky, J., Ed.; Interscience: New
York, 1970; (b) Hudson, D. J. Org. Chem. 1988, 53, 617–
624.
3. Mrozik, H.; Jones, H.; Friedman, J.; Schwartzkopf, G.;
Schardt, R. A.; Patchett, A. A.; Holff, D. R.; Yakstis, J. J.;
Riek, R. F.; Ostlind, D. A.; Plischker, G. A.; Butler, R.
W.; Cuckler, A. C.; Campbell, W. C. Experientia 1996,
883.
1
150 (5), 121 (15), 65 (40), 58 (100), 41 (10). H NMR
(300 MHz, D2O, NH exchanged): dH (ppm) 2.39 (4H,
3
3
t, JHH = 4.1 Hz, CH2–N–CH2), 2.52 (2H, t, JHH
=
3
6.9 Hz, N–CH2–CH2–NH), 2.98 (2H, t, JHH = 6.9 Hz,
N–CH2–CH2–NH), 3.56 (4H, t, JHH = 4.1 Hz, CH2–
3
3
O–CH2), 7.45 (1H, t, JHH = 7.9 Hz, H-Ar), 8.00 (1H,
3
3
d, JHH = 7.6 Hz, H-Ar), 8.11 (1H, d, JHH = 7.8 Hz,