Reaktion #443022

Reaktionsgleichung

9-chloro-5H-dibenz-[b,e]azepin-6,11-dione

boron dimethylsulfide

methanol

→

solid

Ausbeute 64.7%

9-Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

Ausbeute 64.7%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture refluxed for 3 hours
2. 2
   workup.DISSOLUTION(solids dissolved)
3. 3
   TemperaturThe solution is cooled to room temperature
4. 4
   SonstigeThe volatiles are removed under vacuum
5. 5
   workup.ADDITIONTo the residue is added 100 ml of 2N NaOH
6. 6
   TemperaturThe mixture is refluxed overnight
7. 7
   Filtrationfiltered
8. 8
   ExtraktionThe solid is extracted with dichloromethane
9. 9
   Waschenthe extract is washed with 2N citric acid, water
10. 10
    Trocknendried (Na2SO4)
11. 11
    SonstigeThe solvent is removed

Vorschrift

To a mixture of 7.28 g of 9-chloro-5H-dibenz-[b,e]azepin-6,11-dione in 25 ml of tetrahydrofuran under argon is added 8.5 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is stirred 18 hours at room temperature, 30 ml of tetrahydrofuran added and the mixture refluxed for 3 hours (solids dissolved). The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed overnight and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed to give 4.2 g of solid which is triturated with ethyl acetate-hexane (1:2) to give crystals, m.p. 137° C. to 141° C.

Quelle