Sodium Hydroxide → 2-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

HRID 1291363Notes

Reaction equation

HRID 1291363 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[SH:14].[C:15]([O:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1)(=[O:17])[CH3:16].[OH-].[Na+]>CO>[C:15]([O:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:26]=[CH:27][C:28]([CH2:29][S:14][C:3]3[N:2]([CH3:1])[C:11](=[O:12])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][C:9]=4[CH3:13])[N:4]=3)=[CH:31][CH:32]=2)=[O:24])=[CH:21][CH:20]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189192074-(4-Acetoxybenzoyl)benzyl bromideHCID 178424003HCID 178424003, compound

Product 1

HCID 189188712-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinoneYield 0.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (917 mg), 4-(4-acetoxybenzoyl)benzyl bromide (1.785 g) and 1N-aqueous sodium hydroxide solution (4.5 ml) in methanol (20 ml) was stirred at room temperature for 4 hours. This reaction mixture was concentrated and extracted with chloroform and the extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=6:1) to provide the title compound as colorless solid (4.26 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=6:1)

Sources & evidence

ORD record
ord-61bcea1001e94dbebd84c62c8cf59c3d
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…