Ethanol → 5-(furan-2-yl)imidazolidine-2,4-dione

HRID 2309068Notes

Reaction equation

HRID 2309068 reaction equation
[C-]#N.[K+].[C:4](=[O:7])([O-])[O-].[NH4+:8].[NH4+:9].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O.[CH2:17]([OH:19])C>>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]1[NH:9][C:17](=[O:19])[NH:8][C:4]1=[O:7]

Participants

5

Reactant 4

HCID 702EthanolHCID 7362FurfuralHCID 9032Potassium CyanideHCID 517111Ammonium Carbonate

Product 1

HCID 2260675-(furan-2-yl)imidazolidine-2,4-dioneYield 55%

Conditions

Temperature
55 °C

Procedure

A mixture of powdered potassium cyanide (32.6 g, 0.5 mol), ammonium carbonate (96.0 g, 1 mol) and 2-furaldehyde (24.0 g, 0.25 mol) in 50% aqueous ethanol (650 ml) was heated at 55° C. for 6 hrs. after which the solution was concentrated to two-thirds of its initial volume. The solution was cooled in an ice-bath, acidified with concentrated HCl and left at 0° C. until the product crystallized out. Obtained were 22.7 g (0.137 mol, 55% yield) of 5-(2-furyl)-hydantoin as a tan product: mp 145°-146° C.

Workup

  1. concentrationafter which the solution was concentrated to two-thirds of its initial volume
  2. temperatureThe solution was cooled in an ice-bath
  3. waitleft at 0° C. until the product
  4. customcrystallized out
  5. customObtained

Sources & evidence

ORD record
ord-d407d03ca4b74e6a88cdf231e8cb4d58
Source dataset
uspto-grants-1987_09
Patent number
US04692513

Reaction notes

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