Butylamine → 2-(4-Iodophenyl)acetamide

Participants

Reaction Steps

1-Butylamine (1.83 g) was added to a solution of 4-iodophenylacetyl chloride (2.80 g) in ether (25 ml), and the reaction mixture was stirred at ambient temperature for 5 minutes. The reaction mixture was then partitioned between water (30 ml) and ethyl acetate (50 ml). The organic layer was washed with 2M aqueous hydrochloric acid (25 ml), water (30 ml), brine (25 ml), dried (MgSO4), and evaporated to give N-1-butyl, (4-iodophenyl)acetamide, as a colourless crystalline solid, (2.9 g), mp.: 100-102° C., NMR: 0.82-0.88(3H,t), 1.18-1.43(4H,m), 3.00-3.06(2H,q), 3.35(2H,s), 7.03-7.67(4H,AB), 7.97(H,bt); m/z 318 (M+H).

Provenance & Evidence