Molecules 2018, 23, 3152
13 of 19
◦
1
N,N-Diphenyl-4-acetylamino benzenesulfonyl amide (Ii), Yield 91.6%, white powder, m.p. 233 C. H NMR
(300 MHz, acetone-d6): δ = 2.05–2.14 (m, 3H, Me), 2.90 (s, 1H, CH), 5.70 (br. s, 1H, NH), 7.20–07.6 (m, 14H, Ar).
1
N,N-Dimethyl-4-acetylamino benzenesulfonyl amide (Ij), Yield 80%, white powder, m.p. 149 ◦C. H NMR
(300 MHz, acetone-d6): δ = 2.20 (s, 3H, Me), 2.70 (s, 6H, 2 Me), 5.40 (br. s, 1H, NH), 6.60–7.50 (m, 4H, Ar).
◦
N-Benzyl-N-methyl-4-acetylamino benzenesulfonyl amide (Ik), Yield 78%, white powder, m.p. 154 C. 1H NMR
(300 MHz, acetone-d6):
(m, 4H, Ar).
δ = 2.20 (s, 3H, Me), 2.60 (s, 3H, MeCO), 4.20 (s, 2H, CH2), 7.25–7.36 (m, 5H, Ph), 7.70–7.90
◦
(4-Benzylpiperazino)-4-acetylamino benzenesulfonyl amide (Il), Yield 69%, white powder, m.p. 108 C. 1H NMR
(300 MHz, acetone-d6): = 2.10 (s, 3H, Me), 2.40–2.55 (m, 4H, 2 CH2), 2.90–3.00 (m, 4H, 2 CH2), 3.45–3.55 (m, 2H,
CH2-Ph), 7.10–7.25 (m, 5H, Ph), 7.60–7.80 (d, J = 6.5 Hz, 4H, Ar), 9.50 (br. s, 1H, NH).
δ
◦
(4-Methylpiperazino)-4-acetylamino benzenesulfonyl amide (Im), Yield 81%, white powder, m.p. 198 C. 1H NMR
(300 MHz, acetone-d6):
δ = 2.05 (s, 3H, Me), 2.13 (s, 3H, Me), 2.33 (s, 4H, 2 CH2), 2.78 (s, 4H, 2 CH2), 7.60
(d, J = 6.5 Hz, 2H, Ar), 7.70 (d, J = 6.5 Hz, 2H, Ar), 10.5 (br. s, 1H, NH).
N-(1-Methylbenzimidazole-2-yl)-4-acetylamino benzenesulfonyl amide (In). Yield 24%, white powder, m.p.
◦
168 C. 1H NMR (300 MHz, DMSO-d6):
δ = 2.05–2.15 (m, 3H, Me), 3.20 (s, 3H, Me), 4.70 (br. s, 1H, NH), 7.10–7.80
(m, 8H, Ar), 10.70 (br. s, 1H, NH).
◦
Sulfanilic acid N-methyl amide (IIa), Yield 48%; m.p. 110 C. 1H NMR (300 MHz, acetone-d6):
δ = 1.85 (s, 3H, Me),
5.00 (br. s, 2H, NH2), 6.60 (d, J = 6.5 Hz, 2H, Ar), 7.50 (d, J = 6.5 Hz, 2H, Ar).
1
Sulfanilic acid N-(1-methylethyl) amide (IIb). Yield 68%, white powder, m.p. 116 ◦C. H NMR (300 MHz,
acetone-d6):
δ = 1.04 (s, 3H, Me), 1.06 (s, 3H, Me), 3.25–3.35 (m, 1H, CH), 6.75 (d, J = 6.5 Hz, 2H, Ar), 7.55
(d, J = 6.5 Hz, 2H, Ar).
Sulfanilic acid N-(1,1-dimethylethyl) amide (IIc). Yield 87%, white powder, m.p. 126 ◦C. 1H NMR (300 MHz,
acetone-d6):
δ = 1.20 (s, 9H, 3 Me), 5.30 (br. s, 2H, NH2), 5.90 (br. s, 1H, NH), 6.70 (d, J = 6.5 Hz, 2H, Ar), 7.70
(d, J = 6.5 Hz, 2H, Ar).
Sulfanilic acid N-phenyl amide (IId). Yield 93%, white powder, m.p. 197 ◦C. 1H NMR (300 MHz, acetone-d6):
δ = 5.40 (br. s, 2H, NH2), 6.60–6.90 (m, 4H, Ar), 7.00–7.60 (m, 5H, Ar), 8.20 (br. s, 1H, NH).
Sulfanilic acid N-(2-methoxyphenyl) amide (IIe). Yield 97.2%, white powder, m.p. 205 ◦C. 1H NMR (300 MHz,
DMSO-d6):
δ = 3.70 (s, 3H, Me), 5.40 (br. s, 2H, NH2), 6.65 (d, J = 6.5 Hz, 2H, Ar), 6.90 (d, J = 6.5 Hz, 2H, Ar),
7.05–7.15 (m, 1H, Ar), 7.46–7.50 (m, 3H, Ar), 7.64 (br. s, 1H, NH).
◦
Sulfanilic acid N-benzyl amide (IIf). Yield 99%, white powder, m.p. 120 C. 1H NMR (300 MHz, DMSO-d6):
δ = 4.60 (s, 2H, CH2), 5.40 (br. s, 2H, NH2), 6.65–6.75 (m, 7H, Ar), 6.90 (d, J = 6.5 Hz, 2H, Ar).
1
Sulfanilic acid N-(3-fluorophenyl) amide (IIg). Yield 97%,white powder, m.p. 120 ◦C. H NMR (300 MHz,
DMSO-d6):
δ = 3.91 (d, J = 1.5 Hz, 2H, CH2), 5.90 (s, 1H, Ar), 6.60 (d, J = 8.63 Hz, 1H, Ar), 7.00–7.06 (m, 2H,
Ar), 7.08 (d, J = 7.69 Hz, 1H, Ar), 7.32 (dd, J = 7.35 and 14.33 Hz, 1H, Ar), 7.43 (d, J = 8.61 Hz, 2H, Ar), 7.69 (t,
J = 2.25 Hz, 1H, NH).
1
Sulfanilic acid N-(carboxypropyl) amide (IIh). Yield 86%, white powder, m.p. 129 ◦C. H NMR (300 MHz,
DMSO-d6):
δ = 1.57 (q, J = 7.23 Hz, 2H, CH2), 2.19 (t, J = 7.36 Hz, 2H, CH2), 2.66 (q, J = 7.23 Hz, 2H, CH2), 5.88
(br. s, 2H, NH2), 6.60 (d, J = 8.63 Hz, 2H, Ar), 7.01 (t, J = 5.92 Hz, 1H, NH), 7.39 (d, J = 8.62 Hz, 2H, Ar), 11.99 (br. s,
1H, OH).
Sulfanilic acid N-(bis-phenylmethyl) amide (IIi). Yield 97%, white powder, m.p. 179 ◦C. 1H NMR (300 MHz,
DMSO-d6):
δ = 2.90 (s, 1H, CH), 5.30 (br. s, 1H, NH), 5.60 (br. s, 2H, NH2), 6.60 (d, J = 6.5 Hz, 2H, Ar), 7.15–7.30
(m, 10H, Ar), 7.60 (d, J = 6.5 Hz, 2H, Ar).
◦
Sulfanilic acid N-(1,1-dimethyl) amide (IIj). Yield 94%, white powder, m.p. 175 C. 1H NMR (300 MHz, acetone
d6): δ = 2.50 (s, 6H, 2 Me), 5.40 (br. s, 2H, NH2), 6.60–7.50 (m, 4H, Ar).
◦
1
Sulfanilic acid N-methyl-N-benzyl amide (IIk). Yield 98%, white powder, m.p. 137 C. H NMR (300 MHz,
acetone-d6):
δ = 2.50 (s, 3H, Me), 4.20 (s, 2H, CH2), 5.50 (br. s, 2H, NH2), 6.70 (d, J = 6.5 Hz, 2H, Ar), 7.25–7.35
(m, 5H, Ph), 7.60 (d, J = 6.5 Hz, 2H, Ar).
Sulfanilic acid N-(4-benzylpiperazino) amide (IIl). Yield 89%, white powder, m.p. 244 ◦C. 1H NMR (300 MHz,
acetone-d66 + DMSO-d6 (1:1 v/v)):
δ = 2.35–2.45 (m, 4H, (CH2)2N), 2.40–2.50 (m, 4H, (CH2)2N-SO2), 3.30 (br. s, 2H,
NH2), 3.40 (s, 2H, CH2-Ph), 6.60–7.40 (m, 4H, Ar), 7.30–7.40 (m, 5H, Ph).
◦
Sulfanilic acid N-(4-methylpiperazino) amide (IIm). Yield 92%, white powder, m.p. 212 C. 1H NMR (300 MHz,
DMSO d6): = 2.13 (s, 3H, Me), 2.33 (s, 4H, (CH2)2N), 2.78 (s, 4H, (CH2)2N-SO2), 6.10 (br. s, 2H, NH2), 6.65 (d,
J = 8.45 Hz, 2H, Ar), 7.34 (d, J = 8.36 Hz, 2H, Ar).
δ