4-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline synthesis
- Product Name:4-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline
- CAS Number:54494-12-1
- Molecular formula:C14H11N3O
- Molecular Weight:237.26
28825-12-9
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54494-12-1
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Yield:54494-12-1 83%
Reaction Conditions:
with sodium sulphide nonahydrate in 1,4-dioxane;lithium hydroxide monohydrate at 80; for 0.75 h;Inert atmosphere;
Steps:
5 5-(4′-Aminophenyl)-3-phenyl-1,2,4-oxadiazole (5)
3.1.5
5-(4'-Aminophenyl)-3-phenyl-1,2,4-oxadiazole (5)
A similar procedure
23
to that previously described for the preparation of 1 was followed using 3-phenyl-5-(4'-nitrophenyl)-1,2,4-oxadiazole (47) (0.35 g, 1.32 mmol) in 1,4-dioxane (3 mL) and sodium sulfide nonahydrate (0.76 g, 3.17 mmol) in water (3 mL).
Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 5 as a pale brown solid (0.26 g, 1.10 mmol, 83%). Rf = 0.40 (hexane/ethyl acetate, 1:1); mp 165-170 °C; 1H NMR (400 MHz; CDCl3) δH 4.15 (2H, s, NH2), 6.76 (2H, d, J = 8.8 Hz, H-3', H-5'), 7.49-7.51 (3H, m, ArH), 8.02 (2H, d, J = 8.8 Hz, H-2', H-6') and 8.15 (2H, m, ArH); 13C NMR (100 MHz, CDCl3): δC = 114.0 (C), 114.5 (CH), 127.3 (C), 127.5 (CH), 128.8 (CH), 130.0 (CH), 130.9 (CH), 150.6 (C), 168.6 (C) and 176.0 (C); IR (νmax/cm-1) 689, 748, 1217 (C-N), 1366, 1500, 1604 (N-H), 1739, 2970, 3221, 3324 (N-H) and 3392; MS (ESI, 70 eV) m/z 238 (M+, 100%).
Found (M+, 238.0970), C14H12N3O requires 238.0975.
References:
Conole, Daniel;Beck, Thorsten M.;Jay-Smith, Morgan;Tingle, Malcolm D.;Eason, Charles T.;Brimble, Margaret A.;Rennison, David [Bioorganic and medicinal chemistry]
100-47-0
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613-92-3
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$5.00/250mg
54494-12-1
9 suppliers
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