Reaktion #1058041

Reaktionsgleichung

N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide

N,N-Dimethylethylenediamine

N-(5-chlorothiophen-2-ylmethoxy)phthalimide

acetic acid

→

N-{4-chloro-2-[1-(5-chlorothiophen-2-ylmethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide

Ausbeute 90.0%

Lösungsmittel

EtOH

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 15 h at RT
2. 2
   EinengenThe reaction mixture was concentrated under vacuum
3. 3
   Sonstigethe residue purified by column chromatography (eluting with CH2Cl2/PE, 1:1)

Vorschrift

N,N-Dimethylethylenediamine (178 μL, 1.54 mmol) was added to a solution of N-(5-chlorothiophen-2-ylmethoxy)phthalimide (220 mg, 0.75 mmol) in EtOH (5 mL), and the reaction allowed to stir at RT for 15 h. Glacial acetic acid (1 mL) was then added to adjust the mixture to ca. pH 4 followed by a solution of N-(2-acetyl-4-chlorophenyl)trifluoromethanesulfonamide 19 (211 mg, 0.70 mmol) in EtOH (2 mL), and the mixture stirred for 15 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-(5-chlorothiophen-2-ylmethoxyimino)ethyl]phenyl}trifluoromethanesulfonamide 194 (280 mg, 90%), as white crystals. 1H n.m.r. (400 MHz, CDCl3) δ 11.37, br s, 1H; 7.63, d, J=8.8 Hz, 1H; 7.48, d, J=2.4 Hz, 1H; 7.33, dd, J=2.4 and 8.8 Hz, 1H; 6.94, d, J=3.8 Hz; 6.81, d, J=3.8 Hz; 5.24, s, 2H; 2.33, s, 3H. HRMS (M+) 445.9540.

Quelle