2-Hydroxyimidazole → 4-(Furan-2-carbonyl)-1,3-dihydro-2H-imidazol-2-one

HRID 1995665Notes

Reaction equation

HRID 1995665 reaction equation
[NH:1]1[CH:5]=[CH:4][NH:3][C:2]1=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](Cl)=[O:17]>[N+](C1C=CC=CC=1)([O-])=O>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]([C:5]1[NH:1][C:2](=[O:6])[NH:3][CH:4]=1)=[O:17]

Participants

5

Reactant 3

HCID 222082-HydroxyimidazoleHCID 682422-Furancarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 155675484-(Furan-2-carbonyl)-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To 50 ml of nitrobenzene is added 4.2 g of 1,3-dihydro-2H-imidazol-2-one, 13.3 g of aluminum chloride and 7.2 g of furanoyl chloride. The mixture is stirred at 60° C. for 3 hours and poured over ice water. The solids are filtered, washed with ether and recrystallized twice from ethanol-water to afford the title compounds. M.P. 318°-321° C.

Workup

  1. filtrationThe solids are filtered
  2. washwashed with ether
  3. customrecrystallized twice from ethanol-water

Sources & evidence

ORD record
ord-d48df1cc6e724b4e9711c07a5deba832
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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