Diethylamine → N,N-diethyl-4-formylbenzamide

Participants

Reaction Steps

4-Carboxybenzaldehyde (1.07 g, 7.13 mmol) was added into SOCl2 (5 ml). The mixture was refluxed for 6 hours until the solid was totally dissolved in solution. Then SOCl2 was evaporated under reduced pressure. Toluene (10 ml) was added to the residue and then removed under reduced pressure. The resulting residue was dissolved in anhydrous DCM (10 ml). Et2NH (20 mmol, 2.07 ml) was added dropwise. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the resulting residue was subjected to flash chromatography (EtOAc/Hexanes=30%˜50%) to give compound (1) (1.32 g, 6.44 mmol, yield 90%). 1H NMR (CDCl3) δ 10.06 (s, 1H), 7.95 (d, 2H), 7.55 (d, 2H), 3.58 (quart, 2H), 3.23 (quart, 2H), 1.28 (t, 3H), 1.13 (t, 3H).

Provenance & Evidence