4-(5-ethyl-1,3,4-oxadiazol-2-yl)aniline synthesis
- Product Name:4-(5-ethyl-1,3,4-oxadiazol-2-yl)aniline
- CAS Number:99055-83-1
- Molecular formula:C10H11N3O
- Molecular Weight:189.21
46713-46-6
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99055-83-1
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Yield:99055-83-1 70%
Reaction Conditions:
with sodium sulphide nonahydrate in 1,4-dioxane;lithium hydroxide monohydrate at 80; for 0.75 h;Inert atmosphere;
Steps:
9 2-(4′-Aminophenyl)-5-ethyl-1,3,4-oxadiazole (9)
3.1.9
2-(4'-Aminophenyl)-5-ethyl-1,3,4-oxadiazole (9)
A similar procedure
23
to that previously described for the preparation of 1 was followed using 3-ethyl-5-(4'-nitrophenyl)-1,3,4-oxadiazole (65) (50 mg, 0.23 mmol) in 1,4-dioxane (1 mL) and sodium sulfide nonahydrate (0.13 g, 0.55 mmol) in water (1 mL).
Purification by flash chromatography (hexane/ethyl acetate 1:1) afforded 9 as a pale brown solid (30 mg, 0.16 mmol, 70%). Rf = 0.15 (hexane/ethyl acetate, 2:1); mp 138-142 °C; 1H NMR (400 MHz; CDCl3) δH 1.41 (3H, t, J = 7.6 Hz, CH2CH3), 2.91 (2H, q, J = 7.6 Hz, CH2CH3), 4.05 (2H, s, NH2), 6.72 (2H, d, J = 8.8 Hz, H-3', H-5') and 7.82 (2H, d, J = 8.8 Hz, H-2', H-6'); 13C NMR (100 MHz, CDCl3) δC 10.9 (CH3), 19.1 (CH2), 113.8 (C), 114.6 (CH), 128.8 (CH), 149.5 (C), 165.0 (C) and 166.8 (C); IR (νmax/cm-1) 834, 1175 (C-O), 1366 (C-N), 1497, 1574 (N-H), 1608, 1738, 2924, 3216, 3332 (N-H) and 3446; MS (ESI, 70 eV) m/z 190 (M+, 100%); Found (M+, 190.0975), C10H12N3O requires 190.0975.
References:
Conole, Daniel;Beck, Thorsten M.;Jay-Smith, Morgan;Tingle, Malcolm D.;Eason, Charles T.;Brimble, Margaret A.;Rennison, David [Bioorganic and medicinal chemistry]
122-04-3
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