반응 #40880

반응 방정식

2,5-bis trifluoromethyl benzaldehyde

tert butyl sulfinamide

→

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

수율 91.0%

용매

water

DCM

반응 조건

후처리

1. 1
   온도at reflux for 3 days
2. 2
   추출extracted with DCM
3. 3
   세척The extracts were washed with water
4. 4
   건조dried (MgSO4)
5. 5
   기타evaporated in vacuo to an off white solid which
6. 6
   기타was purified by chromatography (silica, 4-10% EtOAc/isohexane)

실험 절차

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+).

출처