Reaktion #530086

Reaktionsgleichung

2-Trifluoromethylbenzenesulfonyl chloride

3-benzyloxy-5-methylaniline

N-methylmorpholine

→

title compound

Ausbeute 83.1%

3-Benzyloxy-5-methyl-1-(2-trifluoromethylphenylsulfonylamino)benzene

Ausbeute 83.1%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe dichloromethane solution was washed with saturated aqueous NaHCO3 (2×50 mL), 10% HCl (2×50 mL), and brine (2×50 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   SonstigeAfter evaporating the solvent in vacuo
4. 4
   Sonstigethe residue was purified by flash column chromatography (4:1 dichloromethane/hexane)

Vorschrift

2-Trifluoromethylbenzenesulfonyl chloride (490 mg, 2.0 mmol) was added to a solution of 3-benzyloxy-5-methylaniline (426 mg, 2.0 mmol), as prepared in the preceding step, and N-methylmorpholine (0.5 mL) in dichloromethane (10 mL). The mixture was stirred at ambient temperature overnight. After adding additional dichloromethane (100 mL), the dichloromethane solution was washed with saturated aqueous NaHCO3 (2×50 mL), 10% HCl (2×50 mL), and brine (2×50 mL), and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (4:1 dichloromethane/hexane) to give the title compound as white solid (700 mg, 83%). 1H-NMR (300 MHz, CDCl3) δ 7.93 (d, J=7.8 Hz, 1 H), 7.85 (d, J=7.3 Hz, 1 H), 7.63 (t, J=7.7 Hz, 1 H), 7.53 (t,J=7.7 Hz, 1 H), 7.38 (m, 5 H), 6.60 (s, 1 H), 6.55 (s, 2 H), 6.40 (s, 1 H), 4.98 (s, 2 H), 2.20 (s, 3 H).

Quelle