Potassium Iodide → 1-Phenyl-3-(2-bromoethyl)hydantoin

HRID 1380070

Reaktionsgleichung

Reaktionsgleichung von HRID 1380070
[C:1]1([N:7]2[CH2:13][C:11](=[O:12])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[Br:16][CH2:17][CH2:18]Br.[I-].[K+]>C(O)C>[C:1]1([N:7]2[CH2:13][C:11](=[O:12])[N:10]([CH2:18][CH2:17][Br:16])[C:8]2=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 5705761-Phenylimidazolidine-2,4-dione

Produkt 1

HCID 202420731-Phenyl-3-(2-bromoethyl)hydantoin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-phenylhydantoin (5 g, 28.3 mmoles), 85% potassium hydroxide (2.06 g, 31.2 mmoles), 1,2-dibromoethane (11.72 g, 62.4 mmoles) and potassium iodide (catalytic amounts) in 100 ml of ethanol was refluxed for 67 hours. The solid was filtered, the mother liquors were evaporated and the crude product was purified by silica gel column chromatography eluting with increasing mixtures of ethyl acetate in hexane. By crystallization from acetone/hexane 1.56 g of the title compound were obtained, m.p. 146°-147° C.

Aufarbeitung

  1. temperaturewas refluxed for 67 hours
  2. filtrationThe solid was filtered
  3. customthe mother liquors were evaporated
  4. customthe crude product was purified by silica gel column chromatography
  5. washeluting with increasing mixtures of ethyl acetate in hexane
  6. customBy crystallization from acetone/hexane 1.56 g of the title compound
  7. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-d0f6989b5c7a4d11b0dd68edbdf0b8d7
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04579861

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