Reaktion #1853485

Reaktionsgleichung

5-amino-1,2-benzisoxazole

4n-propylbenzenesulphonyl chloride

pyridine

NaHCO3

N2

→

solid

Ausbeute 72.0%

N-benzo[d]isoxazol-5-yl-4-propyl-benzenesulfonamide

Ausbeute 72.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 2 h at room temperature
2. 2
   Extraktionthe mixture was extracted into ethyl acetate (20 mL)
3. 3
   WaschenThe organic phase was washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a residue that
8. 8
   Sonstigewas purified

Vorschrift

To a solution of 4n-propylbenzenesulphonyl chloride (171 mg, 0.783 mmol) in dichloromethane (4 mL).was added pyridine (150 μL, 1.86 mmol) and the mixture was stirred under. N2 for 5 min, after which time 5-amino-1,2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (170 mg, 72%), single spot at Rf 0.68 (1:1 hexane:ethyl acetate). mp 130.0-130.6° C., HPLC purity 99+% (tR 2.44 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 8.62 (1H, d, J=1.0 Hz), 7.60 (2H, d, J=8.4 Hz), 7.48 (2H, m), 7.19 (3H, m), 6.86 (1H, s, N−H), 2.58 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.88 (3H, t, J=7.4 Hz). LCMS: 315.14 (M−). FAB-MS (MH+, C16H16N2O3S): calcd 317.0960, found 317.0962.

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