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

Participants

Reaction Steps

N,N-Dimethylethylenediamine (254 μL, 2.20 mmol) was added to a solution of N-(cyclopentyloxy)phthalimide (345 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 reaction stirred for 2.25 h at RT. The reaction mixture was concentrated under vacuum, and the residue purified by radial thin layer chromatography (eluting with CH2Cl2/PE, 1:19) to afford N-[4-chloro-2-(1-cyclopentyloxyiminoethyl)phenyl]trifluoromethanesulfonamide 163 (185 mg, 48%), as a pale yellow solid. 1H n.m.r. (400 MHz, CDCl3) δ 12.18, br s, 1H; 7.67, d, J=8.8 Hz, 1H, 7.49, d, J=2.4 Hz, 1H, 7.31, dd, J=2.4 and 8.8 Hz, 1H, 4.80, m, 1H, 2.30, s, 3H; 1.89, m, 4H, 1.74, m, 2H, 1.64, m, 2H. HRMS (M+) 384.0518. N-(Cyclopentyloxy)phthalimide was prepared by the procedure of Ishikawa, T.; Kamiyama, K.; Matsunaga, N.; Tawada, H.; lizawa, Y.; Okonogi, K.; Miyake, A. J. Antibiot., 2000, 53, 1071-1085.

Provenance & Evidence