Dipropylamine → N-[4-(N,N-Dipropylaminosulfonyl)phenyl]-3,3,3-trifluro-2-hydroxy-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3,3,3-trifluoro-N-[4-(fluorosulfonyl)phenyl]-2-hydroxy-2-methylpropanamide (0.2 g), di-n-propylamine (0.25 g), and 4-dimethylaminopyridine (13.0 mg) in dry acetonitrile (3 ml) was heated at reflux for 4 days. The reaction mixture was cooled to 22° C., diluted with water (30 ml) and extracted with ethyl acetate (2×15 ml). The combined ethyl acetate extracts were washed with 1N HCl, brine, dried and evaporated to give an oil. The oil was purified by chromatography (12:1 CHCl3 : diethyl ether) to yield an oil which crystallized from hexane to produce the title compound as a colourless crystalline solid (87.5 mg); mp 132°-134° C.; MS: m/z=397(M+1); NMR (250M Hz): 0.77-0.83 (t,6), 1.41-1.49 (m,4), 1.58 (s,3), 2.96-3.02 (t,4), 7.54 (s,1), 7.72-7.75 (m,2), 7.96-7.98 (m,2), 10.36 (s,1). Analysis for C16H23 F3N2O4S: Calculated: C, 48.47; H, 5.85; N, 7.07; Found: C, 48.84; H, 5.90; N, 6.89.

Provenance & Evidence