Hydantoin → 3-(3-Benzyloxypropyl)imidazolidine-2,4-dione

HRID 2068103Notes

Reaction equation

HRID 2068103 reaction equation
[NH:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[CH2:8]([O:15][CH2:16][CH2:17][CH2:18]O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH2:8]([O:15][CH2:16][CH2:17][CH2:18][N:3]1[C:4](=[O:6])[CH2:5][NH:1][C:2]1=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 10006HydantoinHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3479713-Benzyloxy-1-propanol

Product 1

HCID 670192263-(3-Benzyloxypropyl)imidazolidine-2,4-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Imidazolidine-2,4-dione (1.0 g, 9.99 mmol), 3-benzyloxypropan-1-ol (1.91 ml, 12.0 mmol) and triphenylphosphine (3.1 g, 12.0 mmol) were stirred in methylene chloride (20 ml) and cooled to 0° C. Diisopropyl azodicarboxylate (2.36 μl, 12.0 mmol) in dichloromethane (5 ml) was slowly added and the mixture stirred at ambient temperature overnight. The mixture was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 3-(3-benzyloxypropyl)imidazolidine-2,4-dione (1.3 g, 53%, containing 7% w/w triphenylphosphine oxide) as a pale yellow solid.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol (98/2)

Sources & evidence

ORD record
ord-c03970a2f494461e81e55fd60f6da13d
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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