Reaktion #40880

Reaktionsgleichung

2,5-bis trifluoromethyl benzaldehyde

tert butyl sulfinamide

→

N-{(1E)-[2,5-bis(trifluoromethyl)phenyl]methylene}-2-methylpropane-2-sulfinamide

Ausbeute 91.0%

Lösungsmittel

water

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3 days
2. 2
   Extraktionextracted with DCM
3. 3
   WaschenThe extracts were washed with water
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated in vacuo to an off white solid which
6. 6
   Sonstigewas purified by chromatography (silica, 4-10% EtOAc/isohexane)

Vorschrift

A mixture of 2,5-bis trifluoromethyl benzaldehyde (21.5 g, 88.8 mmol), tert butyl sulfinamide (16.1 g, 133 mmol) and anhydrous CuSO4 (16.5 g, 103 mmol) in DCM (94 ml) was stirred at room temperature for 16 hours and at reflux for 3 days. The fine suspension was diluted with water and extracted with DCM. The extracts were washed with water, dried (MgSO4) and evaporated in vacuo to an off white solid which was purified by chromatography (silica, 4-10% EtOAc/isohexane) to give the desired N-{(1E)-[2,5-bis(trifluoromethyl)phenyl]methylene}-2-methylpropane-2-sulfinamide as a white crystalline solid (14.8 g, 91%); 1H NMR δ (ppm)(CDCl3): 8.98 (1 H, d, J=1.8 Hz), 8.46 (1 H, s), 7.92-7.85 (2 H, m), 1.29 (9 H, s); m/z (ES+) 346 (MH+).

Quelle