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

HRID 1291364Notes

Reaction equation

HRID 1291364 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].[Si]([O:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1)(C(C)(C)C)(C)C.[OH-].[Na+]>CO>[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[S:14][CH2:33][C:32]1[CH:31]=[CH:30][C:29]([C:27](=[O:28])[C:26]2[CH:37]=[CH:38][C:23]([OH:22])=[CH:24][CH:25]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18918912HCID 18918912, compoundHCID 178424003HCID 178424003, compound

Product 1

HCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinoneYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (952 mg), 4-(4-t-butyldimethylsilyloxybenzoyl)benzyl bromide (2.90 g) and 1N-aqueous sodium hydroxide solution (4.6 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=19:1). The resulting 2-[4-(4-t-butyldimethylsilyloxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone was dissolved in tetrahydrofuran (15 ml). To this solution was added 1M tetrabutylammonium fluoride/tetrahydrofuran (3.8 ml), and the mixture was stirred at room temperature for 1 hour. This reaction mixture was diluted with water and the resulting precipitate was collected by filtration, rinsed with water, and dried to provide the title compound as colorless solid (1.332 g).

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=19:1)
  7. dissolutionThe resulting 2-[4-(4-t-butyldimethylsilyloxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone was dissolved in tetrahydrofuran (15 ml)
  8. additionTo this solution was added 1M tetrabutylammonium fluoride/tetrahydrofuran (3.8 ml)
  9. additionThis reaction mixture was diluted with water
  10. filtrationthe resulting precipitate was collected by filtration
  11. washrinsed with water
  12. customdried

Sources & evidence

ORD record
ord-4ff04bb3bbe844b7a75b4b7400d549b2
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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