Reaktion #62645

Reaktionsgleichung

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

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product

Ausbeute 48.0%

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

Ausbeute 48.0%

Lösungsmittel

phosphorus oxychloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder nitrogen, was heated
2. 2
   Temperaturunder reflux for 6 hours
3. 3
   SonstigeThe excess phosphorus oxychloride was removed under vacuum with gentle warming
4. 4
   TemperaturThe 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
   Sonstigetriturated until all the material
8. 8
   SonstigeThe organic phase was separated
9. 9
   Waschenwashed with 2N sodium hydroxide solution, twice with water
10. 10
    Trocknendried over anhydrous sodium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo to an oil
13. 13
    workup.DISSOLUTIONThe oil was dissolved in 50 ml of ethyl acetate
14. 14
    Einengenthe solution was concentrated under a stream of nitrogen
15. 15
    FiltrationAt a volume of about 30 ml, the mixture was filtered
16. 16
    SonstigeConcentration of the filtrate was continued to a volume of about 20 ml, during which crystallization
17. 17
    Sonstigeresulted
18. 18
    workup.DISSOLUTIONThe solid was dissolved
19. 19
    Temperaturby heating
20. 20
    Filtrationthe hot solution was filtered
21. 21
    Sonstigeto crystallize

Vorschrift

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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