Isopropylamine → 2,4-Imidazolidinedione, 1-(1-methylethyl)-

HRID 591734Notes

Reaction equation

HRID 591734 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].[CH:9](N)([CH3:11])[CH3:10]>CN(C=O)C>[CH:9]([N:8]1[CH2:2][C:3](=[O:4])[NH:5][C:6]1=[O:7])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 78516(2-Chloroacetyl)urea

Product 1

HCID 102194852,4-Imidazolidinedione, 1-(1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

(2-Chloroacetyl)-urea (0.68 g, 5.00 mmol) and isopropylamine (0.86 mL, 10.0 mmol) in DMF (10 mL) was stirred for 6 h at room temperature and then heated to 135° C. for 4 hours. DMF was removed under vacuum and the residue was purified by column chromatography (silica gel 230-400 mesh; eluting with hexane:dichloromethane:ethyl acetate 2.5:1.0:0.5) to give 1-isopropyl-imidazolidine-2,4-dione as a white solid. Yield: 0.20 g (28%).

Workup

  1. customDMF was removed under vacuum
  2. customthe residue was purified by column chromatography (silica gel 230-400 mesh; eluting with hexane:dichloromethane:ethyl acetate 2.5:1.0:0.5)

Sources & evidence

ORD record
ord-176ed72556f5435d9021f74b7ad07faa
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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