3-Methoxy-N-methylbenzenamine (3j)22. Oil, 1H NMR
(500 MHz, CDCl3) d 7.08 (t, J = 8.0 Hz, 1H, ArH), 6.27 (dd, J
= 8.0 Hz and 2.3 Hz, 1H, ArH), 6.23 (dd, J = 8.0 Hz and 2.1 Hz,
1H, ArH), 6.15 (t, J = 2.2 Hz, 1H, ArH), 3.71 (br s, 1H, NH),
3.77 (s, 3H, OCH3), 2.81 (s, 3H, NCH3); 13C NMR (125 MHz,
CDCl3) d 160.7, 150.7, 129.8, 105.5, 102.2, 98.2, 54.9, 30.5.
N,2-Dimethylbenzenesulfonamide (5e)28. mp 70–72 uC; 1H
NMR (500 MHz, CDCl3) 7.96 (d, J = 8.1 Hz, 1H, ArH), 7.46
(t, J = 7.3 Hz, 1H, ArH), 7.33 (t, J = 6.4 Hz, 2H, ArH), 4.47 (br
s, 1H, NH), 2.64–2.63 (m, 6H, CH3); 13C NMR (125 MHz,
CDCl3) d 137.0, 136.7, 132.7, 132.5, 129.6, 126.0, 28.9, 20.2.
N,4-Dimethylbenzenesulfonamide (5f)29. mp 75–76 uC; 1H
NMR (500 MHz, CDCl3) 7.75 (d, J = 8.2 Hz, 2H, ArH), 7.32
(d, J = 8.1 Hz, 2H, ArH), 4.46 (br s, 1H, NH), 2.64 (d, J =
5.5 Hz, 3H, CH3N), 2.43 (s, 3H, CH3); 13C NMR (125 MHz,
CDCl3) d 143.4, 135.7, 129.6, 127.2, 29.2, 21.4.
N-Methylnaphthalen-1-amine (3k)15. Oil, 1H NMR (500 MHz,
CDCl3) d 7.67–7.60 (m, 3H, ArH), 7.36 (t, J = 7.6 Hz, 1H, ArH),
7.19 (t, J = 7.3 Hz, 1H, ArH), 6.87 (dd, J = 8.5 Hz and 2.5 Hz,
1H, ArH), 6.79 (d, J = 2.5 Hz, 1H, ArH), 3.86 (br s, 1H, NH),
2.92 (s, 3H, CH3); 13C NMR (125 MHz, CDCl3) d 147.0, 135.3,
128.8, 127.6, 127.5, 126.3, 125.9, 121.9, 117.9, 103.7, 30.7
4-Methoxy-N-methylbenzenesulfonamide (5g)30. mp 94–95 uC
1
(lit.30 mp 96–98.5 uC); H NMR (500 MHz, CDCl3) d 7.80 (d, J
N-Methylpyridin-2-amine (3l)23. Oil, 1H NMR (500 MHz,
CDCl3) d 8.08 (d, J = 5.1 Hz, 1H, ArH), 7.42 (t, J = 7.9 Hz, 1H,
ArH), 6.56 (t, J = 5.9 Hz, 1H, ArH), 6.37 (d, J = 8.5 Hz, 1H,
ArH), 4.65 (br s, 1H, NH), 2.90 (s, 3H, CH3); 13C NMR
(125 MHz, CDCl3) d 159.5, 147.8, 137.3, 112.4, 106.0, 28.9.
= 8.6 Hz, 2H, ArH), 6.99 (d, J = 8.6 Hz, 2H, ArH), 4.43 (br s,
1H, NH), 3.87 (s, 3H, CH3O), 2.63 (d, J = 5.4 Hz, 3H, CH3N);
13C NMR (125 MHz, CDCl3) d 162.8, 130.2, 129.2, 114.2, 55.5,
29.1.
1
N-Methylbenzenesulfonamide (5h)31. Oil, H NMR (500 MHz,
N,5-Dimethylpyridin-2-amine (3m)24. Oil, 1H NMR (500 MHz,
CDCl3) 7.90 (s, 1H, ArH), 7.26 (d, J = 8.0 Hz, 1H, ArH), 6.32 (d,
J = 8.5 Hz, 1H, ArH), 4.46 (br s, 1H, NH), 2.88 (s, 3H, CH3N),
2.16 (s, 3H, CH3); 13C NMR (125 MHz, CDCl3) 157.7, 147.3,
138.3, 121.1, 105.7, 29.1, 17.1.
CDCl3) d 7.87 (d, J = 7.9 Hz, 2H, ArH), 7.59 (t, J = 7.4 Hz, 1H,
ArH), 7.53 (t, J = 7.6 Hz, 2H, ArH), 4.60 (br s, 1H, NH), 2.66 (d,
J = 5.1 Hz, 3H, CH3); 13C NMR (125 MHz, CDCl3) d 138.7,
132.6, 129.0, 127.1, 29.1.
N-Methylnaphthalene-2-sulfonamide (5i)32. mp 107–108 uC; 1H
NMR (500 MHz, CDCl3) d 8.44 (s, 1H, ArH), 7.97 (d, J =
8.6 Hz, 2H, ArH), 7.91 (d, J = 8.2 Hz, 1H, ArH), 7.84 (d, J = 8.6
Hz, 1H, ArH), 7.65 (t, J = 7.2 Hz, 1H, ArH), 7.61 (t, J = 7.1 Hz,
1H, ArH), 4.59 (br s, 1H, NH), 2.69 (d, J = 5.4 Hz, 3H, CH3);
13C NMR (125 MHz, CDCl3) d 135.4, 134.7, 132.0, 129.4, 129.1,
128.7, 128.6, 127.8, 127.4, 122.2, 29.2.
N-Methylpyrazin-2-amine (3n)25. Oil, 1H NMR (500 MHz,
CDCl3) d 7.99 (s, 1H, ArH), 7.89 (s, 1H, ArH), 7.79 (s, 1H,
ArH), 4.82 (br s, 1H, NH), 2.97 (d, J = 5.2 Hz, 3H, CH3); 13C
NMR (125 MHz, CDCl3) d 155.2, 141.7, 132.0, 131.7, 28.0.
3-Chloro-N-methylbenzenesulfonamide (5a)26. mp 44–45 uC;
1H NMR (500 MHz, CDCl3) d 7.86 (s, 1H, ArH), 7.75 (d, J =
7.5 Hz, 1H, ArH), 7.56 (d, J = 7.5 Hz, 1H, ArH), 7.48 (t, J =
7.7 Hz, 1H, ArH), 4.53 (br s, 1H, NH), 2.69 (s, 3H, CH3); 13C
NMR (125 MHz, CDCl3) d 140.5, 135.2, 132.8, 130.4, 127.2,
125.2, 29.2.
N-Methylbenzo[d]thiazol-2-amine (7a)33. mp 155–156 uC (lit.33
mp 141–142 uC); 1H NMR (500 MHz, CDCl3) d 7.59 (d, J = 7.6
Hz, 1H, ArH), 7.53 (d, J = 8.0 Hz, 1H, ArH), 7.29 (t, J = 7.5 Hz,
1H, ArH), 7.08 (t, J = 7.5 Hz, 1H, ArH), 5.86 (br s, 1H, NH),
3.10 (s, 3H, CH3N); 13C NMR (125MHz, CDCl3) d 168.9, 152.4,
130.2, 125.9, 121.2, 120.8, 118.5, 31.6.
4-Bromo-N-methylbenzenesulfonamide (5b)27. mp 74–75 uC
1
(lit.27 mp 76–77 uC); H NMR (500 MHz, CDCl3) 7.73 (d, J =
8.3 Hz, 2H, ArH), 7.67 (d, J = 8.4 Hz, 2H, ArH), 4.47 (br s, 1H,
NH), 2.67 (d, J = 4.3 Hz, 3H, CH3); 13C NMR (125 MHz,
CDCl3) 137.8, 132.3, 128.7, 127.6, 29.2.
N,6-Dimethylbenzo[d]thiazol-2-amine (7b)34. mp 155–156 uC
1
(lit.34 mp 153 uC); H NMR (500 MHz, CDCl3) d 7.43–7.40 (m,
2H, ArH), 7.09 (d, J = 7.8 Hz, 1H, ArH), 5.85 (br s, 1H, NH),
3.08 (s, 3H, CH3N), 2.38 (s, 3H, CH3); 13C NMR (125MHz,
CDCl3) d 168.1, 150.3, 131.0, 130.4, 127.0, 120.8, 118.2, 31.6,
21.1.
N-Methyl-4-(trifluoromethyl)benzenesulfonamide (5c). mp 76–
1
78 uC; H NMR (500 MHz, CDCl3) 8.00 (d, J = 8.2 Hz, 2H,
ArH), 7.80 (d, J = 8.3 Hz, 2H, ArH), 4.57 (br s, 1H, NH), 2.71 (s,
3H, CH3); 13C NMR (125 MHz, CDCl3) d 142.5, 134.5 (q, JC-F
32.9 Hz), 127.7, 126.3 (q, JC-F = 3.6 Hz), 123.2 (q, JC-F
=
=
N-Methyl-6-phenoxybenzo[d]thiazol-2-amine (7c). mp 158–
159 uC; 1H NMR (500 MHz, CDCl3) d 7.49 (d, J = 8.6 Hz,
1H, ArH), 7.31 (t, J = 7.9 Hz, 2H, ArH), 7.26 (s, 1H, ArH), 7.06
(t, J = 7.3 Hz, 1H, ArH), 7.01 (dd, J = 8.6 Hz and 2.2 Hz, 1H,
ArH), 6.98 (d, J = 7.9 Hz, 2H, ArH), 5.49 (br s, 1H, NH), 3.10 (s,
3H, CH3N); 13C NMR (125MHz, CDCl3) d 168.1, 158.2, 151.4,
148.8, 131.2, 129.6, 122.6, 119.1, 118.3, 117.9, 111.9, 31.6;
HRMS-EI (70 eV) m/z calcd for C14H13N2OS [M+H]+ 257.0749,
found 257.0747.
271.5 Hz), 29.2; HRMS-EI (70 eV) m/z calcd for C8H8NO2F3NaS
[M+Na]+ 262.0126, found 262.0131.
N-Methyl-4-(trifluoromethoxy)benzenesulfonamide (5d). Oil,
1H NMR (500 MHz, CDCl3) d 7.93 (dt, J = 9.2 Hz and
2.4 Hz, 2H, ArH), 7.36 (d, J = 8.2 Hz, 2H, ArH), 4.57 (q, J = 5.0
Hz, 1H, NH), 2.69 (d, J = 5.4 Hz, 3H, CH3); 13C NMR (125
MHz, CDCl3) d 152.1 (d, JC-F = 1.8 Hz), 137.2, 129.3, 120.2 (q,
JC-F = 257.7 Hz), 29.2; HRMS-EI (70 eV) m/z calcd for
C8H8NO3F3NaS [M+Na]+ 278.0075, found 278.0077.
N-Methyl-6-(methylthio)benzo[d]thiazol-2-amine (7d). mp 155–
156 uC; 1H NMR (500 MHz, CDCl3) 7.56 (s, 1H, ArH),7.45 (d, J
8650 | RSC Adv., 2012, 2, 8645–8652
This journal is ß The Royal Society of Chemistry 2012