Ethyl 6-bromohexanoate → Win-67722

HRID 128888

Reaktionsgleichung

Reaktionsgleichung von HRID 128888
[CH3:1][C:2]([NH:4][C:5]1[C:10]([I:11])=[C:9]([NH:12][C:13]([CH3:15])=[O:14])[C:8]([I:16])=[C:7]([C:17]([O-:19])=[O:18])[C:6]=1[I:20])=[O:3].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C=O>[C:13]([NH:12][C:9]1[C:8]([I:16])=[C:7]([C:6]([I:20])=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[C:10]=1[I:11])[C:17]([O:19][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:18])(=[O:14])[CH3:15]

Komponenten

4

Edukt 2

HCID 117544Ethyl 6-bromohexanoateHCID 23672589Sodium Amidotrizoate

Produkt 1

HCID 9918530Win-67722Ausbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium diatrizoate (16.1 g, 25.3 mmol) was dissolved in 180 ml of dry dimethylformamide and to this solution was added, in one portion, ethyl 6-bromohexanoate (4.5 ml, 25.3 mmol). The reaction mixture was stirred for 12 hr at ambient temperature and then poured into 1.6 1 of ice-water with stirring. The resulting white precipitate was collected by filtration, dissolved in 1:1 ethanol-ethyl acetate and the solution was treated sequentially with magnesium sulfate, decolorizing charcoal and then filtered through a short pad of silica gel. The filtrate was concentrated to dryness and dried to give 16 g (84%) of the desired product. Recrystallization from methanol-water gave analytically pure material, mp 235°-238° C. (decomp. at 275° C.); MS:M+ 756. The 1H-NMR (300 MHz) spectral data was consistent with the desired product. Calculated for C19H23I3N2O6 : C 30.18, H 3.07, I 50.35, N 3.70; Found: C 30.26, H 2.88, I 50.40, N 3.65.

Aufarbeitung

  1. stirringwith stirring
  2. filtrationThe resulting white precipitate was collected by filtration
  3. dissolutiondissolved in 1:1 ethanol-ethyl acetate
  4. additionthe solution was treated sequentially with magnesium sulfate
  5. filtrationfiltered through a short pad of silica gel
  6. concentrationThe filtrate was concentrated to dryness
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-17ee4eeb345846629db4d83bfc6951b6
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466433

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