Hydantoin → HCID 59299230, compound

HRID 2065512Notes

Reaction equation

HRID 2065512 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[OH-].[K+].[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Br>CCO.CCOC(C)=O>[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:4]1[C:5](=[O:6])[CH2:7][NH:1][C:2]1=[O:3]

Participants

6

Reactant 3

HCID 10006HydantoinHCID 14797Potassium HydroxideHCID 699793-Bromobenzyl bromide

Product 1

HCID 59299230HCID 59299230, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydantoin (300 mg, 3.0 mmol) was added to a solution of KOH (202 mg, 3.6 mmol) in 90% EtOH at r.t., and the reaction stirred for 30 min. 3-Bromobenzyl bromide (750 mg, 3.0 mmol) was added, and the reaction was heated at reflux for 18 h. The solution was diluted with EtOAc, washed with H2O and brine, dried (MgSO4) and concentrated in vacuo. Precipitation from 50% EtOAc/hexanes followed by collection by filtration gave 512 mg (63%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.42 (d, J=7.6 Hz, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.19 (t, J=7.6 Hz, 1H), 5.81 (s, 1H), 4.63 (s, 2H), 4.00 (s, 2H). [M+H] calc'd for C10H9BrN2O2, 269, 271; found, 269, 271.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 18 h
  3. washwashed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPrecipitation from 50% EtOAc/hexanes
  7. filtrationfollowed by collection by filtration

Sources & evidence

ORD record
ord-253d29e4da4141fc93fe156f8962c426
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Reaction notes

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