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Helvetica Chimica Acta – Vol. 95 (2012)
125.5 (40), 113.5 (50), 111.5 (38), 77 (100). Anal. calc. for C14H11Cl2NO2 (296.15): C 56.78, H 3.74, N 4.72;
found: C 56.86, H 3.80, N 4.81.
N-(4-Bromophenyl)-N-[(4-chlorophenyl)hydroxymethyl]formamide (5e): Yield 3.337 g (98%).
White solid. M.p. 124 – 1268. IR (KBr): 3288 (OH), 3100, 2900, 1639 (C¼O), 1589, 1488 (C¼C, Ar).
1H-NMR ((D6)DMSO): 5.11 (s, CHꢀOH); 6. 58 (s, OH); 7.45 – 7.67 (m, 8 arom. H); 10.10 (s, CHO).
13C-NMR ((D6)DMSO): 73.7; 115.8; 122.2; 128.6; 128.8; 132.3; 132.8; 138.3; 140.1; 171.5. MS: 343 (4),
341 (15), 339 (10, Mþ), 200 (18), 198 (18), 143 (55), 141 (70), 171 (48), 169 (48), 113.5 (45), 111.5 (60), 77
(100). Anal. calc. for C14H11BrClNO2 (340.61): C 49.37, H 3.25, N 4.11; found: C 49.51, H 3.30, N 4.18.
N-[Hydroxy(4-nitrophenyl)methyl]-N-(4-methylphenyl)formamide (5f): Yield 2.634 g (92%). Yel-
low liquid. IR (KBr): 3340 (OH), 3090, 2910, 1649 (C¼O), 1520, 1595 (C¼C, Ar), 1350, 1530. 1H-NMR
((D6)DMSO): 2.21 (s, Me); 5.28 (s, CHꢀOH); 6.80 (s, OH); 7.07, 7.54, 7.79, 8.22 (2 AA’BB’, JAB ¼ 7.4, 2.9,
8 arom. H); 9.97 (s, CHO). 13C-NMR ((D6)DMSO): 21.0; 73.4; 120.5; 123.6; 127.9; 129.5; 134.0; 135.5;
147.4; 148.2; 170.5. MS: 287 (<2, [M þ 1]þ), 286 (11, Mþ),152 (85), 134 (55), 122 (60), 105 (76), 91 (100),
77 (95). Anal. calc. for C15H14N2O2 (286.29): C 62.93, H 4.93, N 9.78; found: C 71.20, H 5.59, N 11.06.
N-(4-Bromophenyl)-N-[hydroxy(4-methylphenyl)methyl]formamide (5g): Yield 3.074 g (96%).
Pale yellow solid. M.p. 155 – 1578. IR (KBr): 3285 (OH), 3090, 2910, 1642 (C¼O), 1490, 1580 (C¼C,
Ar), 1350, 1530. 1H-NMR ((D6)DMSO): 2.27 (s, Me); 5.01 (s, CHꢀOH); 6. 40 (s, OH); 7.13 – 7.69 (m, 8
arom. H); 10.05 (s, CHO). 13C-NMR ((D6)DMSO): 22.0; 73.0; 120.0; 127.0; 129.1; 130.0; 132.0; 133.0;
135.0; 141.0; 171.0. MS: 321 (12, Mþ (81Br)), 319 (12, Mþ (79Br)), 200 (40), 198 (40), 171 (60), 169 (60),
157 (46), 155 (46), 120 (70), 91 (100), 77 (85). Anal. calc. for C15H14BrNO2 (320.19): C 56.26, H 4.41, N
4.37; found: C 56.59, H 4.55, N 4.40.
N-[(4-Chlorophenyl)hydroxymethyl]-N-(4-methylphenyl)formamide (5h): Yield 2.675 g (96%).
White solid. M.p. 142 – 1448. IR (KBr): 3286 (OH), 3090, 2920, 1638 (C¼O), 1489, 1598 (C¼C, Ar).
1H-NMR ((D6)DMSO): 2.23 (s, Me); 5.09 (s, CHꢀOH); 6. 50 (s, OH); 7.07 – 7.56 (m, 8 arom. H); 9.86 (s,
CHO). 13C-NMR ((D6)DMSO): 20.9; 73.7; 120.2; 128.5; 128.8; 129.5; 132.7; 133.1; 136.2; 140.4; 171.0.
MS: 277 (6, Mþ (37Cl)), 275 (14, Mþ (35Cl)), 143 (25), 141 (60), 134 (60), 113.5 (20), 111.5 (55), 105 (45),
91 (96), 77 (100). Anal. calc. for C15H14ClNO2 (275.74): C 65.34, H 5.12, N 5.08; found: C 65.45, H 5.16, N
5.10.
N-(4-Bromophenyl)-N-[hydroxy(4-nitrophenyl)methyl]formamide (5i): Yield 3.160 g (90%). Yel-
low liquid. IR (KBr): 3289 (OH), 3100, 2900, 1649 (C¼O), 1589, 1488 (C¼C, Ar). 1H-NMR
((D6)DMSO): 5.10 (s, CHꢀOH); 6. 54 (s, OH); 6.95, 7.50, 7.71, 8.31 (2 AA’BB’, JAB ¼ 7.4, 2.9, 8 arom. H);
10.10 (s, CHO). 13C-NMR ((D6)DMSO): 75.9; 122.3; 128.9; 129.2; 129.7; 130.1; 132.1; 134.1; 143.6; 171.5.
MS: 341 (10, Mþ (81Br)), 339 (10, Mþ (79Br)), 200 (18), 198 (18), 143.5 (55), 141.5 (70), 171 (48), 169
(48), 113.5 (45), 111.5 (60), 77 (100); Anal. calc. for C14H11BrN2O4 (351.17): C 47.88, H 3.15, N 7.98;
found: C 48.10, H 3.20, N 8.03.
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