Acetic Acid → N-[4-chloro-2-(1-cyclopropylmethoxyiminoethyl)phenyl]trifluoromethanesulfonamide

Participants

Reaction Steps

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(cyclopropylmethoxy)phthalimide (326 mg, 1.50 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (2 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (302 mg, 1.0 mmol) in EtOH (2 mL), and the mixture stirred for 48 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1) to afford N-[4-chloro-2-(1-cyclopropylmethoxyiminoethyl)phenyl]trifluoromethanesulfonamide 187 (300 mg, 81%), as a white solid. M.p. 53-54° C. 1H n.m.r. (400 MHz, CDCl3) δ 11.84, br s, 1H; 7.65, d, J=8.8 Hz, 1H; 7.49, d, J=2.4 Hz, 1H; 7.32, dd, J=2.4 and 8.8 Hz, 1H; 4.03, d, J=7.2 Hz, 2H; 2.34, s, 3H; 1.22, m, 1H; 0.64, m, 2H; 0.34, m, 2H.

Provenance & Evidence