The Journal of Organic Chemistry
Page 10 of 16
Hz, 1H), 7.39 (t, J = 8.0 Hz, 2H), 7.29 (d, J = 6.4 Hz, 1H), 7.17 (t, J = 7.6 Hz, 1H), 6.75-6.72 (m, 2H), 5.52 (br, 2H). 13C{ H} NMR (600
1
+
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
MHz, CDCl
3
) δ 167.2, 149.4, 134.8, 133.1, 129.1, 127.7, 127.2, 124.6, 123.3, 121.7, 117.7, 116.9, 115.6. HRMS (ESI) m/z [M+H] calcd
for C13
H
13
N
2
O 213.1028, found 213.1020. The characterization data is consistant with reported literature.24
-Amino-N-(2-chlorophenyl)benzamide (5b). Yellow solid (150 mg, 61%). Flash chromatography eluting with hexanes/ethyl acetate (20:1
10:1), R = 0.2 (hexanes/EtOAc = 10/1). Mp 95-97 °C. H NMR (400 MHz, CDCl ) δ 8.45 (d, J = 8.0 Hz, 1H), 8.35 (br, 1H), 7.54 (d, J
f 3
2
→
1
=
7.6 Hz, 1H), 7.40 (d, J = 7.6 Hz, 1H), 7.29 (dd, J = 8.0, 15.6 Hz, 2H), 7.07 (t, J = 7.2 Hz, 1H), 6.74 (t, J = 7.2 Hz, 2H), 5.60 (br, 2H).
13
1
C{ H} NMR (150 MHz, CDCl
3
) δ 167.5, 148.9, 137.8, 132.7, 129.0, 127.1, 124.5, 120.5, 117.5, 116.8, 116.2. HRMS (ESI) m/z
+
25
[
M+H] calcd for C13
H
12ClN
2
O 247.0638, found 247.0631. The characterization data is consistant with reported literature.
2-Amino-N-(2,3-dimethylphenyl)benzamide (5c). White solid (154 mg, 64%). Flash chromatography eluting with hexanes/ethyl acetate
3
) δ 7.63 (br, 1H), 7.53 (d, J = 8.0 Hz, 1H),
.47 (d, J = 7.6 Hz, 1H), 7.28 (d, J = 9.6 Hz, 1H), 7.16 (t, J = 7.6 Hz, 1H), 7.08 (d, J = 7.6 Hz, 1H), 6.73 (t, J = 7.2 Hz, 2H), 5.56 (br, 2H),
) δ 167.8, 149.2, 137.6, 135.3, 132.7, 130.3, 127.7, 127.2, 125.9, 122.6, 117.5,
16.7, 115.9, 20.59, 14.0. HRMS (ESI) m/z [M+H] calcd for C15 O 241.1341, found 241.1339. The characterization data is
consistant with reported literature.
-Amino-N-(3-bromophenyl)benzamide (5d). Yellow solid (174 mg, 60%). Flash chromatography eluting with hexanes/ethyl acetate (20:1
= 0.2 (hexanes/EtOAc = 10/1). Mp 155-157 °C. H NMR (400 MHz, CDCl ) δ 7.86 (s, 1H), 7.79 (br, 1H), 7.45 (t, J = 6.4 Hz,
f 3
) δ 167.6, 149.3,
2
39.4, 133.2, 130.4, 127.5, 127.2, 123.5, 122.8, 119.0, 117.8, 117.1, 115.8. HRMS (ESI) m/z [M+H] calcd for C13H12BrN O 291.0133,
1
(20:1 → 10:1), R
f
= 0.3 (hexanes/EtOAc = 10/1). Mp 115-116 °C. H NMR (400 MHz, CDCl
7
2
1
1
3
1
.34 (s, 3H), 2.22 (s, 3H). C{ H} NMR (150 MHz, CDCl
3
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
+
17 2
H N
26
2
1
→ 10:1), R
1
3
1
2H), 7.27 (d, J = 8.0 Hz, 2H), 7.24-7.20 (m, 1H), 6.71 (t, J = 7.6 Hz, 2H), 5.50 (br, 2H). C{ H} NMR (150 MHz, CDCl
1
found 291.0128. The characterization data is consistant with reported literature.
2
3
+
2
7
-Amino-N-(3,5-dimethylphenyl)benzamide (5e). White solid (187 mg, 78%). Flash chromatography eluting with hexanes/ethyl acetate
3
) δ 7.70 (br, 1H), 7.47 (d, J = 8.0 Hz, 1H),
.29 (d, J = 5.2 Hz, 1H), 7.23 (s, 2H), 6.83 (s, 1H), 6.73 (t, J = 8.0 Hz, 2H), 5.52 (br, 2H), 2.36 (s, 6H). C{ H} NMR (150 MHz, CDCl )
δ 167.5, 148.9, 138.7, 137.6, 132.6, 127.1, 126.2, 118.3, 117.5, 116.8, 116.4, 21.4. HRMS (ESI) m/z [M+H] calcd for C15H N O
17 2
241.1341, found 241.1339. The characterization data is consistant with reported literature.
-Amino-N-(p-tolyl)benzamide (5f). White solid (165 mg, 73%). Flash chromatography eluting with hexanes/ethyl acetate (20:1 → 10:1),
1
(20:1 → 10:1), R
f
= 0.3 (hexanes/EtOAc = 10/1). Mp 160-162 °C. H NMR (400 MHz, CDCl
13
1
7
3
+
2
6
2
1
R
=
f 3
= 0.3 (hexanes/EtOAc = 10/1). Mp 148-150 °C. H NMR (165mg, 400 MHz, CDCl ) δ 7.78 (br, 1H), 7.48 (t, J = 7.2 Hz, 3H), 7.29 (d, J
6.0 Hz, 1H), 7.20 (d, J = 8.0 Hz, 2H), 6.74 (t, J = 7.6 Hz, 2H), 5.52 (br, 2H), 2.37 (s, 3H). 13C{ H} NMR (150 MHz, CDCl
1
) δ 167.5,
O 227.1184, found
3
+
1
2
2
48.9, 135.2, 134.2, 132.6, 129.5, 127.1, 120.7, 117.5, 116.8, 116.4, 20.9. HRMS (ESI) m/z [M+H] calcd for C14
H
15
N
2
26
27.1180. The characterization data is consistant with reported literature.
-Amino-N-(4-methoxyphenyl)benzamide (5g). White solid (164 mg, 68%). Flash chromatography eluting with hexanes/ethyl acetate
3
) δ 7.74 (br, 1H), 7.49 (d, J = 8.4 Hz, 3H),
.29 (d, J = 6.8 Hz, 1H), 6.94 (d, J = 8.8 Hz, 2H), 6.73 (t, J = 7.6 Hz, 2H), 5.51 (br, 2H), 3.84 (s, 3H). C{ H} NMR (150 MHz, CDCl
1
(20:1 → 10:1), R
f
= 0.3 (hexanes/EtOAc = 10/1). Mp 114-116 °C. H NMR (400 MHz, CDCl
1
3
1
7
1
2
2
3
) δ
+
67.5, 156.6, 148.9, 132.6, 130.8, 127.1, 122.6, 117.5, 116.8, 116.4, 114.8, 114.2, 55.5. HRMS (ESI) m/z [M+H] calcd for C14
H
15
N
2
O
2
2
8
43.1134, found 243.1131. The characterization data is consistant with reported literature.
-Amino-N-(4-chlorophenyl)benzamide (5h). Gray solid (157 mg, 64%). Flash chromatography eluting with hexanes/ethyl acetate (20:1
= 0.2 (hexanes/EtOAc = 10/1). Mp 142-144 °C. H NMR (400 MHz, CDCl ) δ 7.72 (br, 1H), 7.50 (d, J = 8.4 Hz, 2H), 7.43 (d,
f 3
) δ 167.4,
2
149.0, 136.4, 132.9, 129.4, 129.0, 127.1, 121.7, 117.6, 116.9, 115.8. HRMS (ESI) m/z [M+H] calcd for C13H12ClN O 247.0638, found
247.0630. The characterization data is consistant with the reported literature.
-Amino-4-chloro-N-phenylbenzamide (5i). White solid (184 mg, 75%). Flash chromatography eluting with hexanes/ ethyl acetate (20:1
f 3
= 0.2 (hexanes/EtOAc = 10/1). Mp 138-140 °C. H NMR (400 MHz, CDCl ) δ 7.69 (br, 1H), 7.54 (d, J = 7.6 Hz, 2H), 7.37 (t,
) δ 167.0,
50.2, 138.7, 137.7, 129.2, 128.6, 124.9, 120.8, 117.0, 116.9, 114.6. HRMS (ESI) m/z [M+H] calcd for C13H12ClN O 247.0638, found
2
1
→
10:1), R
13
1
J = 7.6 Hz, 1H), 7.30 (d, J = 8.4 Hz, 2H), 7.23 (s, 2H), 6.69 (t, J = 7.2 Hz, 2H), 5.47 (br, 2H). C{ H} NMR (150 MHz, CDCl
3
+
2
8
2
1
→
10:1), R
1
3
1
J = 8.0 Hz, 3H), 7.16 (t, J = 6.8 Hz, 1H), 6.71 (s, 1H), 6.67 (d, J = 8.4 Hz, 1H), 5.62 (br, 2H). C{ H} NMR (150 MHz, CDCl
3
+
1
2
27
47.0631. The characterization data is consistant with reported literature.
2-Amino-4-methoxy-N-phenylbenzamide (5j). White solid (198 mg, 82%). Flash chromatography eluting with hexanes/ ethyl acetate
(20:1 → 10:1), R = 0.3 (hexanes/EtOAc = 10/1). Mp 152-154 °C. H NMR (400 MHz, CDCl ) δ 7.63 (br, 1H), 7.54 (d, J = 8.0 Hz, 2H),
f 3
.41 (d, J = 8.8 Hz, 1H), 7.36 (t, J = 7.6 Hz, 2H), 7.13 (t, J = 7.2 Hz, 1H), 6.28 (d, J = 8.8 Hz, 1H), 6.18 (s, 1H), 5.71 (br, 2H), 3.80 (s, 3H).
1
7
1
3
1
C{ H} NMR (150 MHz, CDCl
3
) δ 167.5, 163.4, 151.5, 138.2, 129.2, 129.0, 124.4, 120.7, 109.3, 104.5, 100.9, 55.4. HRMS (ESI) m/z
+
243.1134, found 243.1133. The characterization data is consistant with reported literature.29
[
M+H] calcd for C14
H
15
N
2
O
2
2
R
-Amino-N-benzylbenzamide (5k). White solid (180 mg, 80%). Flash chromatography eluting with hexanes/ ethyl acetate (20:1 → 10:1),
= 0.3 (hexanes/EtOAc = 10/1). Mp 123-125 °C. H NMR (400 MHz, CDCl ) δ 7.35-7.31 (m, 6H), 7.21 (t, J = 7.6 Hz, 1H), 6.69 (d, J =
f 3
1
13
1
8
.0 Hz, 1H), 6.63 (t, J = 7.6 Hz, 1H), 6.35 (br, 1H), 5.56 (br, 2H), 4.60 (d, J = 5.6 Hz, 2H). C{ H} NMR (150 MHz, CDCl
3
) δ 169.1,
+
148.8, 132.4, 128.7, 127.8, 127.5, 127.0, 117.3, 116.6, 115.8, 43.7. HRMS (ESI) m/z [M+H] calcd for C14H N O 227.1184, found
15 2
2
9
2
2
1
6
27.1177. The characterization data is consistant with reported literature.
-Amino-N-cyclohexylbenzamide (5l). White solid (113 mg, 52%). Flash chromatography eluting with hexanes/ ethyl acetate (20:1 →
= 0.2 (hexanes/EtOAc = 10/1). Mp 153-155 °C. H NMR (400 MHz, CDCl ) δ 7.28 (d, J = 8.0 Hz, 1H), 7.19 (t, J = 7.6 Hz, 1H),
f 3
.65 (dd, J = 7.6, 14.8 Hz, 2H), 5.89 (br, 1H), 5.47 (br, 2H), 3.92 (td, J = 7.2, 14.4 Hz, 1H), 2.01 (d, J = 9.6 Hz, 2H), 1.75 (dd, J = 3.6, 10.0
Hz, 2H), 1.65 (d, J = 12.8 Hz, 1H), 1.42 (dd, J = 12.4, 24.8 Hz, 2H), 1.23 (dt, J = 8.8, 18.0 Hz, 3H). C{ H} NMR (150 MHz, CDCl
68.4, 148.5, 132.0, 127.0, 117.2, 116.7, 116.5, 48.3, 33.2, 25.6, 24.9. HRMS (ESI) m/z [M+H] calcd for C13H N O 219.1497, found
1
0:1), R
13
1
3
) δ
+
1
19 2
2
7
219.1494. The characterization data is consistant with reported literature.
2-(Benzo[d]thiazol-2-yl)aniline (5m). Yellow solid (169 mg, 75%). Flash chromatography eluting with hexanes/ ethyl acetate (50:1 →
= 0.4 (hexanes/EtOAc = 10/1). Mp 120-122 °C. H NMR (400 MHz, CDCl ) δ 7.99 (d, J = 8.0 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H),
f 3
.73 (d, J = 8.0 Hz, 1H), 7.47 (t, J = 7.6 Hz, 1H), 7.37 (t, J = 7.6 Hz, 1H), 7.24 (t, J = 8.0 Hz, 1H), 6.78 (dd, J = 8.0, 18.4 Hz, 2H), 6.42 (br,
1
2
7
2
0:1), R
1
3
1
3
H). C{ H} NMR (150 MHz, CDCl ) δ 169.2, 153.7, 146.7, 133.3, 131.6, 130.3, 126.0, 124.8, 122.4, 121.2, 116.9, 116.8, 115.3. HRMS
+
30
(ESI) m/z [M+H] calcd for C13
11 2
H N S 227.0643, found 227.0636. The characterization data is consistant with reported literature.
N,N'-(1,2-Phenylene)bis(2-aminobenzamide) (5n). White solid (297 mg, 86%). Flash chromatography eluting with hexanes/ ethyl acetate
(20:1 → 10:1), R = 0.3 (hexanes/EtOAc = 5/1).Mp 217-218 °C. H NMR (400 MHz, DMSO-d ) δ 7.84 (d, J = 7.6 Hz, 2H), 7.58 (br, 4H),
f 6
7.20 (dd, J = 2.8, 5.6 Hz, 4H), 7.14 (d, J = 7.6 Hz, 2H), 6.84 (d, J = 8.0 Hz, 2H), 6.65 (t, J = 7.6 Hz, 2H). C{ H} NMR (150 MHz,
1
1
3
1
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10