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Sodium hydride → 3-(3-{4-[(6-Hydroxyhexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione

HRID 857091
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 857091
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([NH:22][C:23]([NH:25][CH2:26][C:27]([O:29]CC)=O)=[O:24])[CH:19]=[CH:20][CH:21]=1)(=O)C.[H-].[Na+]>C(O)C>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([N:22]2[C:27](=[O:29])[CH2:26][NH:25][C:23]2=[O:24])[CH:19]=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 21867037Ethyl N-({[3-(4-{[6-(acetyloxy)hexyl]oxy}butyl)phenyl]amino}carbonyl)glycinate

Produkt 1

HCID 218671563-(3-{4-[(6-Hydroxyhexyl)oxy]butyl}phenyl)imidazolidine-2,4-dioneAusbeute 112,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of ethyl N-({[3-(4-{[6-(acetyloxy)hexyl]oxy}butyl)phenyl]amino}-carbonyl)glycinate (2.967 g) in ethanol (30 ml) was treated under nitrogen with sodium hydride (60% oil dispersion; 280 mg) and the mixture was stirred for 18 h. The solvent was removed under reduced pressure, the residue was dissolved in acetic acid (10 ml) and conc. HBr (1 ml) and the mixture was heated to 75° C. for 1 h. The solvent was removed under reduced pressure, the residue was partitioned between EtOAc and brine. The organic solution was washed with brine, dried and evaporated to dryness. The residue was dissolved in MeOH (30 ml), SOCl2 (0.5 ml) was added, and the solution was stirred for 2 h. The solvent was removed under reduced pressure to give the title compound (2.67 g) ES+ve 349 (MH)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in acetic acid (10 ml)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between EtOAc and brine
  5. washThe organic solution was washed with brine
  6. customdried
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in MeOH (30 ml)
  9. additionSOCl2 (0.5 ml) was added
  10. stirringthe solution was stirred for 2 h
  11. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7865f67f42b9442fa95e1467b8cc04d0
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07144908B2

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