Hydrochloric Acid → HCID 21867183, compound

HRID 857126Notes

Reaction equation

HRID 857126 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C>[CH2:17]([N:10]1[C:11](=[O:13])[CH2:12][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[C:9]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 218671771-(3-Iodophenyl)-2,4-imidazolidinedione

Product 1

HCID 21867183HCID 21867183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Iodophenyl)imidazolidine-2,4-dione (0.5 g) was taken up in dry DMF (10 ml) and treated with sodium hydride (60% oil dispersion, 73 mg) and stirred for 20 min under nitrogen. Benzyl bromide (0.295 ml) was added and stirring continued for 3 h. 2M HCl (100 ml) was added and the mixture extracted with EtOAc. The combined extracts were washed with saturated aqueous sodium hydrogen carbonate (50 ml), brine (50 ml) and dried (MgSO4). This was recrystallised from MeOH to give the title compound (0.255 g). LCMS RT 3.53 min.

Workup

  1. stirringstirring
  2. waitcontinued for 3 h
  3. extractionthe mixture extracted with EtOAc
  4. washThe combined extracts were washed with saturated aqueous sodium hydrogen carbonate (50 ml), brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customThis was recrystallised from MeOH

Sources & evidence

ORD record
ord-dcd6f19d0f474d478dc5b878332a5e60
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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