Sodium Hydroxide → N-(2-Bromobenzyl)-2,2-diethoxyacetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl diethoxyacetate (20.0 g, 114 mmol) in ethanol (50 ml) was added a solution of sodium hydroxide (4.56 g, 114 mmol) in water (25 ml), and the resulting mixture heated at reflux for 5 hours. The mixture was evaporated to dryness, and the residue dried in vacuo. The resulting solid (22.75 g, 0.13 mol) was dissolved in dry ether (88 ml) and to this mixture was added thionyl chloride (13.3 g, 0.11 mol) with stirring for 10 minutes at 10° C. The reaction mixture was heated at reflux for 30 minutes and then allowed to cool. A solution of 2-bromobenzylamine (20.73 g, 0.11 mol) in toluene (57 ml) and pyridine (34 ml) was poured into this reaction mixture with vigorous stirring. This was heated at reflux for 30 minutes and then allowed to cool. The mixture was poured into ice water and extracted with toluene (×3). The organic extracts were combined and washed firstly with 2% HCl and then water. The solvent was evaporated and the residue purified by flash chromatography on silica gel (9:1 hexane:ethyl acetate) to give the title compound (15.6 g, 44%).

Provenance & Evidence