Benzoyl Peroxide → 5-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one

HRID 1702486Notes

Reaction equation

HRID 1702486 reaction equation
[C:1]([N:4]1[C:8]([CH3:9])=[C:7]([C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:6]([C:20](=[O:22])[CH3:21])[C:5]1=[O:23])(=[O:3])[CH3:2].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:9][C:8]1[N:4]([C:1](=[O:3])[CH3:2])[C:5](=[O:23])[N:6]([C:20](=[O:22])[CH3:21])[C:7]=1[C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 128560311,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-5-methyl-2H-imidazol-2-one

Product 1

HCID 128560325-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 55.5 g (0.176 mole) of 1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-5-methyl-2H-imidazol-2-one, 37.4 g (0.210 mole) of N-bromosuccinimide and about 100 mg of benzoyl peroxide in 500 ml of carbon tetrachloride is stirred at reflux temperature for 4 hours. The mixture is then cooled and filtered to remove the succinimide which formed. The solvent is evaporated from the filtrate and the resulting residue is crystallized from a mixture of 300 ml of ethyl acetate and 300 ml of hexane to give 5-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one melting at about 135°-136° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered
  4. customto remove the succinimide which
  5. customformed
  6. customThe solvent is evaporated from the filtrate
  7. customthe resulting residue is crystallized from a mixture of 300 ml of ethyl acetate and 300 ml of hexane

Sources & evidence

ORD record
ord-7397e18ebd044d26a3c35dea8e4d08e6
Source dataset
uspto-grants-1983_04
Patent number
US04381393

Reaction notes

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