4-Hydroxybenzylamine → 3-(3,5-Dichloro-4-(4-methoxybenzyloxy)phenyl)-N-(4-hydroxybenzyl)-1,2,4-oxadiazole-5-carboxamide

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Reaction Steps

Ethyl 3-(3,5-dichloro-4-(4-methoxybenzyloxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (4 g, 9.46 mmol) and 4-hydroxybenzylamine (2.33 g, 18.91 mmol) were heated in EtOH (150 mL) at 80° C. forming a yellow solution. After 1 h a colourless precipitate formed and the mixture was cooled to room temperature. The solid was filtered off, washed with EtOH and dried in a vacuum oven giving the title compound (4.16 g, 8.32 mmol, 88%) as a colourless solid. 1H NMR δ (ppm) (DMSO-d6): 3.81 (2 H, s), 4.41 (2 H, d, J=6.08 Hz), 5.12 (2 H, s), 6.76 (2 H, d, J=8.08 Hz), 7.00 (2 H, d, J=8.20 Hz), 7.20 (2 H, d, J=8.06 Hz), 7.49 (2 H, d, J=8.18 Hz), 8.13 (2 H, s), 9.38 (1 H, s), 9.95 (1 H, t, J=6.15 Hz). LCMS (10 cm_esci_AmmBicarb_MeCN) tR 4.18 min; m/z 498 [M]−.

Provenance & Evidence