1142
Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides
J. Braz. Chem. Soc.
N-(4-Methoxyphenyl)acetamide (3h)
(Lit.27 159-160 °C); IR (KBr) n / cm-1 3429, 1654, 1546,
1504, 1427, 1342, 1280, 1018, 960, 775, 721, 605; 1H NMR
(500 MHz, CDCl3) d 2.24 (s, 3H, CH3), 7.39-7.48 (m, 3H,
CH), 7.67 (dl, 1H, J 8.0 Hz, CH), 7.77-7.8 (m, 4H, CH);
13C NMR (125 MHz, CDCl3) d 24.1, 121.0, 121.6, 125.6,
125.9, 126.0, 128.6, 134.1, 169.2.
Gray solid, 61.6 mg, 76% yield; m.p. 126.2-127.3 °C
(Lit.27 126-128 °C); IR (KBr) n / cm-1 3444, 1651, 1604,
1562, 1512, 1465, 1411, 1369, 1319; 1H NMR (500 MHz,
CDCl3) d 2.1 (s, 3H, CH3), 3.80 (s, 3H, OCH3), 6.86 (d,
2H, J 8.5 Hz, CH), 7.40 (d, 2H, J 8.5 Hz, CH), 7.49 (brs,
1H, NH); 13C NMR (125 MHz, CDCl3) d 24.3, 55.5, 114.1,
122.0, 131.0, 156.4, 168.4.
N,N’-(1,2-Phenylene)diacetamide (3n)
Brown solid, 75.2 mg, 80% yield; m.p. 188.3-189.1 °C
(Lit.27 188.2-188.7 °C); IR (KBr) n / cm-1 3232, 3024, 1666,
1610, 1535, 1462, 1367, 1313, 1111, 1035, 972, 765, 713,
680, 605; 1H NMR (500 MHz, CDCl3) d 2.08 (s, 6H, CH3),
7.14-7.17 (m, 2H, CH), 7.27-7.29 (m, 2H, CH ), 8.44 (brs,
2H, NH); 13C NMR (125 MHz, CDCl3) d 23.7, 125.5,
126.1, 130.6, 169.9.
N-(4-Methoxy-2-nitrophenyl)acetamide (3i)
Yellow solid, 80.4 mg, 78% yield; m.p. 117.8-118.9 °C
(Lit.27 118 °C); IR (KBr) n / cm-1 3475, 1705, 1627, 1581,
1512, 1458, 1365, 1319, 1288, 1249, 1149, 1072, 1033,
921, 871, 844, 790, 759, 632; 1H NMR (500 MHz, CDCl3)
d 2.26 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 7.64 (s, 1H, CH),
7.22 (d, 1H, J 8.5 Hz, CH), 8.62 (d, 1H, J 8.5 Hz, CH),
10.02 (brs, 1H, NH); 13C NMR (125 MHz, CDCl3) d 25.4,
55.9, 108.5, 123.4, 123.9, 128.5, 154.9, 168.8.
N,N’-([1,1’-Biphenyl]-4,4’-diyl)diacetamide (3o)
Gray solid, 131.1 mg, 98% yield; m.p. 326.2-326.7 °C
(Lit.27 325 °C); IR (KBr) n / cm-1 3290, 1658, 1597, 1577,
1519, 1396, 1365, 1319, 1284, 1176, 1111, 1006, 817, 752,
663; 1H NMR (500 MHz, CDCl3) d 2.30 (s, 6H, CH3), 7.42
(d, 4H, J 8.5 Hz, CH), 7.50 (d, 4H, J 8.5 Hz, CH), 9.28
(brs, 1H, NH); 13C NMR (125 MHz, CDCl3) d 29.7, 115.4,
115.5, 120.2, 126.8, 127.3, 127.7.
N-(2,4-Dichlorophenyl)acetamide (3j)
Gray solid, 40.1 mg, 40% yield; m.p. 143.6-144.7 °C
(Lit.27 144-145 °C); IR (KBr) n / cm-1 3456, 1666, 1585,
1523, 1473, 1384, 1300, 1253, 1145, 1099, 1056, 1010,
1
964, 945, 860, 817, 767, 690, 663; H NMR (500 MHz,
CDCl3) d 2.2 (s, 3H, CH3 ), 7.22 (dd, 1H, J 8.5, 2.0 Hz,
CH), 7.36 (d, 1H, J 2.0 Hz, CH), 7.56 (brs, 1H, NH), 8.31
(d, 1H, J 7.5 Hz, CH); 13C NMR (125 MHz, CDCl3) d 24.8,
122.4, 127.9, 128.7, 133.4, 168.2.
N,N’-(3,3’-Dimethyl-[1,1’-biphenyl]-4,4’-diyl)diacetamide
(3p)
Gray solid, 143.6 mg, 97% yield; m.p. 313.1-314.3 °C
(Lit.27 312 °C); IR (KBr) n / cm-1 3278, 1654, 1649,
1583, 1516, 1490, 1431, 1365, 1317, 1284, 1128, 1039,
1018, 950, 867, 819, 709, 659, 613; 1H NMR (500 MHz,
DMSO-d6) d 2.06 (s, 3H, CH3), 2.24 (s, 3H, CH3), 7.40 (dl,
1H, J 8.0 Hz, CH), 7.47 (m, 2H, CH), 9.29 (s, 1H, NH);
13C NMR (125 MHz, DMSO-d6) d 18.5, 23.8, 124.3, 125.6,
128.7, 132.1, 136.2, 136.7, 168.7.
N-(3,4-Dichlorophenyl)acetamide (3k)
Brown solid, 98.4 mg, 98% yield; m.p. 122.4-123.4 °C
(Lit.27 121.9-123.3 °C); IR (KBr) n / cm-1 3417, 1666, 1589,
1531, 1473, 1388, 1365, 1307, 1257, 1126, 1014, 871, 813,
721, 678, 609; 1H NMR (500 MHz, CDCl3) d 2.17 (s, 3H,
CH3 ), 7.29-7.35 (m, 2H, CH), 7.66 (brs, 1H, CH), 7.72
(brs, 1H, NH); 13C NMR (125 MHz, CDCl3) d 24.5, 119.1,
121.6, 127.5, 130.5, 132.8, 137.4, 168.7.
N-(Thiazol-2-yl)acetamide (5a)
Yellow solid, 61.0 mg, 43% yield; m.p. 201.7-202.1 °C
(Lit.28 202-203 °C), IR (KBr) n / cm-1 3448, 1689,1566,
1427, 1369, 1296, 1230, 1168, 1068, 1041, 995, 972, 875,
821, 779, 709, 659, 628; 1H NMR (500 MHz, CDCl3) d 2.34
(s, 3H, CH3), 6.99 (d, 1H, J 3.5 Hz, CH), 7.44 (d, 1H,
J 3.5 Hz, CH), 12.58 (brs, 1H, NH); 13C NMR (125 MHz,
CDCl3) d 23.1, 135.0, 136.1, 160.3, 168.1.
N-(2-Hydroxy-5-nitrophenyl)acetamide (3l)
Brown solid, 54.9 mg, 56% yield; m.p. 270.2-271.3 °C
(Lit.27 271-272 °C); IR (KBr) n / cm-1 3417, 1658, 1589,
1539, 1500, 1423, 1334, 1292, 1080, 1026, 945, 894, 821,
748, 682, 640; 1H NMR (500 MHz, DMSO-d6) d 2.12 (s,
3H, CH3), 6.99 (d, 1H, J 9.0 Hz, CH), 7.86 (dd, 1H, J 9.0,
2.5 Hz, CH), 8.90 (d, 1H, J 2.5 Hz, CH), 9.41 (brs, 1H,
NH), 11.50 (brs, 1H, OH); 13C NMR (125 MHz, DMSO-d6)
d 24.3, 108.7, 113.5, 113.6, 115.1, 116.9, 120.9, 127.3,
139.6, 134.2, 169.8.
N-(Benzothiazol-2-yl)acetamide (5b)
White solid, 90.2 mg, 94% yield; m.p. 182.3-183.2 °C
(Lit.28 182-183 °C), IR (KBr) n / cm-1 3448, 1693, 1604,
1546, 1446, 1369, 1269, 1076, 1049, 999, 860, 759, 725,
675, 628; 1H NMR (500 MHz, CDCl3) d 2.28 (s, 3H, CH3),
7.33 (t, 1H, J 7.5 Hz, CH), 7.46 (t, 1H, J 7.5 Hz, CH), 7.77
N-(Naphthalen-1-yl)acetamide (3m)
Purple solid, 80.1 mg, 87% yield; m.p. 158.8-159.5 °C