Reaktion #816425

Reaktionsgleichung

HCl

Potassium tert-butoxide

N-(tert-butyl)-1-phenylmethanesulfonamide

diethyl oxalate

→

title compound

2-tert-Butyl-4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe THF was evaporated
2. 2
   Extraktionthe residue was extracted with DCM
3. 3
   SonstigeThe mixture was evaporated
4. 4
   Sonstigethe residue was triturated in petroleum ether
5. 5
   Sonstigethe solvent was decanted

Vorschrift

Potassium tert-butoxide (0.845 g, 10.56 mmol) was added to a solution of N-(tert-butyl)-1-phenylmethanesulfonamide (1.2 g, 5.28 mmol) and diethyl oxalate (0.85 mL, 6.33 mmol) in THF (8 mL) and the mixture was heated at 150° C. for 15 mins in a microwave reactor. The reaction mixture was acidified with 1M HCl, the THF was evaporated and the residue was extracted with DCM. The mixture was evaporated, the residue was triturated in petroleum ether and the solvent was decanted to give the title compound (7 g, 63%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.44-7.32 (m, 5H), 3.90 (br s, 1H), 1.36 (s, 9H); Mass Spectrum: M−H+280

Quelle