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

HRID 370551Notes

Reaction equation

HRID 370551 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-46e419fdf6944052b4e684af276ec488
Source dataset
uspto-grants-1985_07
Patent number
US04526981

Reaction notes

Loading…