2-Furancarbonyl chloride → 4-(Furan-2-carbonyl)-5-methyl-1,3-dihydro-2H-imidazol-2-one

HRID 1995662Notes

Reaction equation

HRID 1995662 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>[N+](C1C=CC=CC=1)([O-])=O>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([C:6]1[NH:5][C:4](=[O:7])[NH:3][C:2]=1[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 155675494-(Furan-2-carbonyl)-5-methyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a slurry of 8.9 g of 1,3-dihydro-4-methyl-2H-imidazol-2-one and 24.0 g of aluminum chloride in 135 ml of nitrobenzene is added 12.9 g of furanoyl chloride in a dropwise manner. The mixture is stirred at 60° C. for 3 hours, cooled and poured over ice water. The solid is then filtered and recrystallized twice from methyl alcohol to afford the title compound. M.P. 214°-216° C.

Workup

  1. temperaturecooled
  2. filtrationThe solid is then filtered
  3. customrecrystallized twice from methyl alcohol

Sources & evidence

ORD record
ord-f7278724f54c40c19d2e3a2ed7c48cb9
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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