Phenacyl bromide → 3,5-Dimethyl-2-[4-(4-phenacyloxybenzoyl)benzylthio]-4-(3H)-quinazolinone

HRID 1291378Notes

Reaction equation

HRID 1291378 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:31](Br)[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][N:23]1[C:22](=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:26])[N:15]=[C:14]1[S:13][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:31][C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:33])=[CH:30][CH:29]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 189192383,5-Dimethyl-2-[4-(4-phenacyloxybenzoyl)benzylthio]-4-(3H)-quinazolinoneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (413 mg), phenacyl bromide (315 mg) and potassium carbonate (436 mg) in DMF (7 ml) was stirred at room temperature for 15 hours. This reaction mixture was concentrated and the residue was dissolved in chloroform, washed with water, dried, and concentrated. The residue was recrystallized from chloroform-ethyl acetate to provide the title compound as colorless solid (313 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record
ord-677699f60dc042a898c85d79f5510111
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…