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

HRID 1380070

Reaction equation

HRID 1380070 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d0f6989b5c7a4d11b0dd68edbdf0b8d7
Source dataset
uspto-grants-1986_04
Patent number
US04579861

Linked notes

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