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

HRID 4021

Reaktionsgleichung

Reaktionsgleichung von HRID 4021
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:4]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+].[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].O>C(Cl)(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[C:3]([NH:2][C:26]([N:25]([CH3:29])[CH3:24])=[O:27])[CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6598Dimethylcarbamoyl Chloride3×HCID 516892Sodium Bicarbonate3×HCID 138233211-(2-Amino-4-bromophenyl)indoline hydrochloride

Produkt 1

HCID 13823369N-[5-bromo-2-(2,3-dihydro-1H-indol-1-yl)phenyl]-N',N'-dimethylureaAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred mixture, under nitrogen, of 28.9 g (0.10 mole) of 1-(2-amino-4-bromophenyl)indoline hydrochloride and 16.8 g (0.20 mole) of anhydrous powdered sodium bicarbonate in 500 ml of chloroform was added a solution of 21.5 g (0.20 mole) of dimethylcarbamyl chloride in 25 ml of chloroform, over a 10 minute period. The mixture was heated under reflux for 7 hours, and 8.4 g (0.10 mole) of sodium bicarbonate and 10.7 g (0.10 mole) of the dimethylcarbamyl chloride were added. After heating under reflux for 2 days, equivalent amounts (8.4 g of sodium bicarbonate and 10.7 g of dimethylcarbamyl chloride) were added. After three days under reflux, the mixture was cooled and 500 ml of water was added. The phases were stirred vigorously for 0.5 hours and separated. The organic phase was washed three times with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in 200 ml of dichloromethane and adsorbed on a chromatography column containing 1 kg of silica gel packed in and eluted with dichloromethane. The fractions containing product were combined and concentrated to afford 14.5 g (40%) of product. Recrystallization from toluene (charcoal)/hexane gave the analytical sample, mp 119°-121° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter heating
  4. temperatureunder reflux for 2 days
  5. temperatureAfter three days under reflux
  6. temperaturethe mixture was cooled
  7. customseparated
  8. washThe organic phase was washed three times with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue was dissolved in 200 ml of dichloromethane
  12. additioncontaining 1 kg of silica gel
  13. washeluted with dichloromethane
  14. additionThe fractions containing product
  15. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bdf54aa101ac42ae9c74e2e30e8f117d
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723007

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