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

HRID 373845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373845
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([CH3:30])([CH3:29])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21]1)=[O:12].O>CN(C)C=O>[CH3:9][C:10]([CH3:30])([CH3:29])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Br:1])[CH:26]=2)[NH:21]1)=[O:12]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 197613982,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Produkt 1

HCID 197614342,2-Dimethyl-N-[2-(5-bromo-2,3-dihydro-1H-indol-2-yl)phenyl]propanamideAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 4.0 g N-bromosuccinimide in 40 ml anhydrous DMF (dimethylformamide) was added dropwise at 5° C. (ice bath) over 20 minutes to a solution of 6.0 g 2,2-dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide in 60 ml DMF. After stirring for one hour additionally, the resulting solution was poured into excess water and the precipitated solid was collected, washed, and taken up in Et2O. The extract was washed with water and brine, dried (MgSO4) and concentrated to give 7.2 g solid. Recrystallization from cyclohexane gave 2.2 g needles, m.p. 173°-175° C.

Aufarbeitung

  1. customthe precipitated solid was collected
  2. washwashed
  3. washThe extract was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dda34a840aed4a688e78c54ee08690e5
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166170

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