Reaktion #1077982

Reaktionsgleichung

H2O

4-Isothiocyanato-benzenesulfonamide

tert-butyldimethylsilyl chloride

Sodium hydride

→

4-isothiocyanato-N-(TBDMS)-benzenesulfonamide

Ausbeute 80.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ether (2×50 mL)
2. 2
   WaschenOrganics were washed with brine (25 mL)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigePurification by silica gel chromatography

Vorschrift

4-Isothiocyanato-benzenesulfonamide (750 mg, 3.5 mmol), and tert-butyldimethylsilyl chloride (528 mg, 3.5 mmol) stirred in dry THF (20 mL) at 0° C. Sodium hydride (210 mg, 60% in mineral oil, 5.25 mmol) was added, and the reaction stirred for 1 h before it was poured over H2O (50 mL) and extracted with ether (2×50 mL). Organics were washed with brine (25 mL), dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography gave 920 mg (80%) of 4-isothiocyanato-N-(TBDMS)-benzenesulfonamide as a white solid. 1H NMR (300 MHz, CDCl3) δ7.86 (d, 2H, J=6.9 Hz), 7.31 (d, 2 H, J=6.9 Hz), 4.40 (s, 1H), 0.90 (s, 9H), 0.22 (s, 6H). Anal. (C13H20N2O2S2Si) C, H, N, S. Calculated C=47.53; H=6.14; N=8.53; S=19.52; found C=47.47; H=6.25; N=8.46; S=19.49.

Quelle