Sodium Hydroxide → beta-Amino-4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-ethanol

Participants

Reaction Steps

A mixture of 5.14 g of N-[1-[4'-[(difluoromethyl)thio][1,1'-biphenyl]-4-yl]-2-hydroxyethyl]benzamide, 9.5 mL of sodium hydroxide solution (1.54 g, 38.5 mmol in 9.5 mL water), and 36 mL of ethanol was boiled for ~40 h. The mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in water, and the aqueous mixture was extracted with 3×70 mL of ethyl acetate. The combined extracts were dried and the solvent was removed under reduced pressure. The white solid obtained was washed with a little ether to give the product 2.69 g (70% yield); m.p. 107.5-110.5° C. IR(Nujol): 3333, 3281, 1597 1313, 1073, 1042, 895, 820 cm-1. 1H-NMR(CDCl3): δ3.56-3.63 (m, 1H), 3.76-3.81 (m, 1H), 4.09-4.13 (m, 1H), 6.86 (t, J=57.0 Hz, 1H), 7.41-7.65 (m, 8H).

Provenance & Evidence