Reacción #46392

Ecuación de reacción

sulphuric acid

N-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophen-5-yl)-2-[(E)-hydroxyimino]acetamide

→

desired compound

Rendimiento 52.5%

3,3-dioxo-1,2,3,6-tetrahydro-3λ6-thieno[3,2-e]indole-7,8-dione

Rendimiento 52.5%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturathe reaction mixture was heated to 90° C.
3. 3
   Temperaturato cool to RT
4. 4
   workup.STIRRINGbriefly stirred
5. 5
   OtroAfter separation of the phases
6. 6
   Otrothe solid which formed
7. 7
   Filtraciónwas filtered off with suction
8. 8
   Lavadowashed with diethyl ether
9. 9
   Otrodried in a drying oven at 50° C. overnight

Procedimiento

6.74 ml (126.38 mmol) of conc. sulphuric acid were introduced into a three-neck round-bottom flask with thermometer and high-efficiency condenser and heated to 70° C. 3.06 g (12.04 mmol) of N-(1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[b]thiophen-5-yl)-2-[(E)-hydroxyimino]acetamide were then added in portions over the course of half an hour, during which the mixture became dark reddish brown in colour. After the addition was complete, the reaction mixture was heated to 90° C. and stirred at this temperature for one hour. For working up, the reaction mixture was allowed to cool to RT and was then added to a mixture of ice-water (110 ml) and ethyl acetate (25 ml) and briefly stirred. After separation of the phases, the solid which formed was filtered off with suction, washed with diethyl ether and dried in a drying oven at 50° C. overnight. 1.50 g of the desired compound were obtained.

Fuente