4-Amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide → 4-(2-Allyloxybenzamido)-1-methyl-3-n-propyl-pyrazole-5-carboxamide

Participants

Reaction Steps

A solution of 2-allyloxybenzoyl chloride (3.93 g, 0.02 mol) in dichloromethane (20 ml) was added dropwise to a stirred, partial solution of 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide (3.64 g, 0.02 mol) in pyridine (50 ml), and the resulting mixture stirred at room temperature overnight in a dry atmosphere. The solvent was evaporated under vacuum and the residue partitioned between dichloromethane (50 ml) and saturated aqueous sodium carbonate solution (50 ml). The organic layer was separated and the aqueous layer exhaustively extracted with further dichloromethane. The combined organic solutions were washed with 2M HCl (3×30 ml), then brine (1×30 ml), and dried (Na2SO4). After filtration and evaporation under vacuum of the filtrate, the crude product was crystallised from ethyl acetate to give the title compound (4.525 g, 66%), m.p. 132°-134° C. Found: C,63.49; H, 6.42; N, 16.33. C18H22N4O3 requires C,63.14; H, 6.48; N, 16.36%.

Provenance & Evidence