1,3-dihydro-4-methyl-2H-imidazol-2-one → 4-(3,4-Dimethoxybenzoyl)-1,3-dihydro-2H-imidazol-2-one

HRID 1995661

Reaction equation

HRID 1995661 reaction equation
C[C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17]([C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 77070Veratroyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 204875614-(3,4-Dimethoxybenzoyl)-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6.5 g of 1,3-dihydro-4-methyl-2H-imidazol-2-one and 14.6 g of aluminum chloride in 65 ml of nitrobenzene is added 17.6 g of 3,4-dimethoxybenzoyl chloride in portions. The mixture is stirred for 3 hours at 60° C., cooled and poured over ice water. The gummy solids are filtered and recrystallized twice from ethyl alcohol-water to afford the title compound. M.P. 257°-259° C.

Workup

  1. temperaturecooled
  2. filtrationThe gummy solids are filtered
  3. customrecrystallized twice from ethyl alcohol-water

Sources & evidence

ORD record
ord-6720dc5fc3df433ea6385c169bd2b31d
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Linked notes

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