반응 #4115

반응 방정식

N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea

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수율 48.0%

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

수율 48.0%

용매

phosphorus oxychloride

반응 조건

후처리

1. 1
   온도under nitrogen, was heated
2. 2
   온도under reflux for 6 hours
3. 3
   기타The excess phosphorus oxychloride was removed under vacuum with gentle warming
4. 4
   온도The residue was chilled in an ice-bath (with exclusion of moisture)
5. 5
   workup.ADDITIONtreated first with 250 ml of ice-cold 2N sodium hydroxide solution
6. 6
   workup.STIRRINGThe mixture was stirred
7. 7
   기타triturated until all the material
8. 8
   기타The organic phase was separated
9. 9
   세척washed with 2N sodium hydroxide solution, twice with water
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    여과filtered
12. 12
    농축concentrated in vacuo to an oil
13. 13
    workup.DISSOLUTIONThe oil was dissolved in 50 ml of ethyl acetate
14. 14
    농축the solution was concentrated under a stream of nitrogen
15. 15
    여과At a volume of about 30 ml, the mixture was filtered
16. 16
    기타Concentration of the filtrate was continued to a volume of about 20 ml, during which crystallization
17. 17
    기타resulted
18. 18
    workup.DISSOLUTIONThe solid was dissolved
19. 19
    온도by heating
20. 20
    여과the hot solution was filtered
21. 21
    기타to crystallize

실험 절차

A mixture of 10.8 g (0.030 mole) of N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylurea and 110 ml of phosphorus oxychloride, under nitrogen, was heated under reflux for 6 hours, with stirring, and then cooled to room temperature. The excess phosphorus oxychloride was removed under vacuum with gentle warming. The residue was chilled in an ice-bath (with exclusion of moisture) and treated first with 250 ml of ice-cold 2N sodium hydroxide solution, and then with 500 ml of dichloromethane. The mixture was stirred and triturated until all the material passed into solution. The organic phase was separated, washed with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to an oil. The oil was dissolved in 50 ml of ethyl acetate and the solution was concentrated under a stream of nitrogen. At a volume of about 30 ml, the mixture was filtered. Concentration of the filtrate was continued to a volume of about 20 ml, during which crystallization resulted. The solid was dissolved by heating, the hot solution was filtered and allowed to crystallize to afford 4.9 g (48%) of product, mp 124°-127° C.

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