Reaktion #459117

Reaktionsgleichung

1-phenyl-3-azabicyclo[3.1.0]hexane

isatoic anhydride

dimethyl sulfoxide

→

product

2'-(1-Phenyl-3-azabicyclo[3.1.0]-hex-3-ylcarbonyl)acetanilide

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 7 g
2. 2
   TemperaturThe mixture is cooled
3. 3
   Sonstigeproducing a gummy solid which
4. 4
   Sonstigeis separated by extraction with chloroform
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated to a dark oil
8. 8
   workup.DISSOLUTIONThis oil is dissolved in 30 ml
9. 9
   Temperaturof acetic anhydride, refluxed for 5 minutes
10. 10
    Sonstigeevaporated to an oil and water
11. 11
    workup.ADDITIONis added
12. 12
    Sonstigedecanted from the mixture several times
13. 13
    workup.ADDITIONThe thick oil is mixed with ethanol
14. 14
    workup.DISSOLUTIONThis solid is dissolved in hot ethanol
15. 15
    Filtrationfiltered
16. 16
    Temperaturcooled
17. 17
    Sonstigegiving a white solid which
18. 18
    Sonstigeis recrystallized once from aqueous ethanol and once from ether

Vorschrift

A mixture of 7 g. of 1-phenyl-3-azabicyclo[3.1.0]hexane and 6.5 g. of isatoic anhydride in 10 ml. of dimethyl sulfoxide is warmed on a steam bath for 10 minutes. The mixture is cooled and water is added producing a gummy solid which is separated by extraction with chloroform, dried, filtered and evaporated to a dark oil. This oil is dissolved in 30 ml. of acetic anhydride, refluxed for 5 minutes, evaporated to an oil and water is added and decanted from the mixture several times. The thick oil is mixed with ethanol and a solid separates. This solid is dissolved in hot ethanol filtered and cooled giving a white solid which is recrystallized once from aqueous ethanol and once from ether to give the product as a white solid, mp 124.5°-127° C.

Quelle