반응 #4114

반응 방정식

thiomorpholine

9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one

sodium hydroxide

→

product

수율 88.0%

9-Bromo-6-(4-thiomorpholinyl)-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine

수율 88.0%

용매

toluene

반응 조건

후처리

1. 1
   온도was heated under nitrogen
2. 2
   기타resulted
3. 3
   온도The mixture was heated
4. 4
   온도under reflux for 3 hours
5. 5
   workup.STIRRINGAfter stirring vigorously for 15 minutes
6. 6
   기타the layers were separated
7. 7
   추출The aqueous phase was extracted with 300 ml of toluene
8. 8
   세척washed once with 2N sodium hydroxide solution, twice with water
9. 9
   건조dried over anhydrous sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo
12. 12
    기타The residue was crystallized from 100 ml of hot methanol

실험 절차

A mixture of 7.88 g (0.025 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 25.8 g (0.250 mole) of thiomorpholine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was heated under reflux for 3 hours, cooled to room temperature and treated with 500 ml of 2N sodium hydroxide solution. After stirring vigorously for 15 minutes, the layers were separated. The aqueous phase was extracted with 300 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was crystallized from 100 ml of hot methanol to give 8.8 g (88%) of product. Recrystallization from a hot solution of dichloromethane (50 ml, charcoal) to which methanol (100 ml) was added provided the analytical sample, mp 165°-167° C.

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