Allantoin → N-[1-(3-Iodobenzyl)-2,5-dioxoimidazolidin-4-yl]urea

HRID 857125

Reaktionsgleichung

Reaktionsgleichung von HRID 857125
[CH:1]1([NH:8][C:9]([NH2:11])=[O:10])[NH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.[H-].[Na+]>CN(C=O)C>[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][N:4]1[C:2](=[O:3])[CH:1]([NH:8][C:9]([NH2:11])=[O:10])[NH:7][C:5]1=[O:6]

Komponenten

5

Edukt 3

HCID 204AllantoinHCID 24758Sodium hydrideHCID 27593613-Iodobenzyl bromide

Produkt 1

HCID 21867061N-[1-(3-Iodobenzyl)-2,5-dioxoimidazolidin-4-yl]ureaAusbeute 13,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Allantoin (1.58 g) was stirred with meta-iodobenzyl bromide (2.97 g) in DMF (25 ml) at 21° under nitrogen and sodium hydride (60% oil dispersion; 0.40 g) was added over 5 min. After 2 h the solution was partitioned between EtOAc and water and hydrochloric acid was added to give pH 3. The separated aqueous layer was extracted with more EtOAc and the combined organic layers were washed with water and brine twice. After drying (MgSO4), the solution was concentrated to 20 ml. After 1 h the solid was collected by filtration and washed with EtOAc. The residue was boiled with EtOAc (50 ml) and the slurry was allowed to cool. The solid was collected by filtration, washed with ethyl acetate and dried to give the title compound (0.507 g). LCMS RT=2.44 min

Aufarbeitung

  1. customAfter 2 h the solution was partitioned between EtOAc and water and hydrochloric acid
  2. additionwas added
  3. customto give pH 3
  4. extractionThe separated aqueous layer was extracted with more EtOAc
  5. washthe combined organic layers were washed with water and brine twice
  6. dry with materialAfter drying (MgSO4)
  7. concentrationthe solution was concentrated to 20 ml
  8. filtrationAfter 1 h the solid was collected by filtration
  9. washwashed with EtOAc
  10. temperatureto cool
  11. filtrationThe solid was collected by filtration
  12. washwashed with ethyl acetate
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-eac4c456015e4dc8826cc4c4d40ecc2b
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144908B2

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