Reaktion #428454

Reaktionsgleichung

m-chloroperbenzoic acid

82

4-{[4-(methylthio)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

sodium thiosulfate

→

83

Ausbeute 30.0%

4-{[4-(methylsulfonyl)-1,3-thiazol-2-yl]carbamoyl}phenyl acetate

Ausbeute 30.0%

Lösungsmittel

water

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting layers separated
2. 2
   WaschenThe organic layer was washed twice with saturated aqueous sodium bicarbonate, once with brine
3. 3
   Trocknendried with anhydrous sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigeto give a beige solid
6. 6
   SonstigeThe crude product was recrystallized from 50% ethyl acetate/hexane (220 mL)
7. 7
   FiltrationAfter 4 days the suspension was filtered
8. 8
   Waschenthe filter pad was washed with hexanes
9. 9
   Trocknendiethyl ether, and dried in vacuo at 55° C. overnight

Vorschrift

A solution of m-chloroperbenzoic acid (1.0 g, 6.0 mmol, maximum 77%) dissolved in dichloromethane (30 mL) was added to a suspension of 82 (0.63 g, 2.0 mmol) in dichloromethane (60 mL). The reaction became homogeneous and the dark brown solution became lighter with time. After 1.25 hours, saturated aqueous sodium thiosulfate was added to the reaction and the reaction mixture was stirred vigorously for 20 minutes. The yellow mixture was diluted with water and the resulting layers separated. The organic layer was washed twice with saturated aqueous sodium bicarbonate, once with brine, dried with anhydrous sodium sulfate and concentrated in vacuo to give a beige solid. The crude product was recrystallized from 50% ethyl acetate/hexane (220 mL). After 4 days the suspension was filtered, the filter pad was washed with hexanes and then diethyl ether, and dried in vacuo at 55° C. overnight to give 83 (0.20 g, 30%) as a light orange solid. Concentration of the filtrate in vacuo followed by triturating the resulting residue with diethyl ether and filtering off the resulting solid yielded an additional 45 mg of 83 as a tan solid.

Quelle