반응 #1376100

반응 방정식

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

boron dimethylsulfide

methanol

→

solid

수율 64.7%

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

수율 64.7%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture refluxed for 3 hours
2. 2
   workup.DISSOLUTION(solids dissolved)
3. 3
   온도The solution is cooled to room temperature
4. 4
   기타The volatiles are removed under vacuum
5. 5
   workup.ADDITIONTo the residue is added 100 ml of 2N NaOH
6. 6
   온도The mixture is refluxed overnight
7. 7
   여과filtered
8. 8
   추출The solid is extracted with dichloromethane
9. 9
   세척the extract is washed with 2N citric acid, water
10. 10
    건조dried (Na2SO4)
11. 11
    기타The solvent is removed

실험 절차

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.

출처