Tetrahydrofuran → 3,5-Dimethyl-2-[4-(4-nitrobenzoyl)benzyl]thio-4(3H)-quinazolinone

HRID 1291355Notes

Reaction equation

HRID 1291355 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].C1COCC1.[OH-].[Na+].[N+:22]([C:25]1[CH:40]=[CH:39][C:28]([C:29]([C:31]2[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>CCO>[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][CH2:35][C:34]1[CH:37]=[CH:38][C:31]([C:29](=[O:30])[C:28]2[CH:39]=[CH:40][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 143775484-Bromomethyl-4'-nitrobenzophenoneHCID 178424003HCID 178424003, compound

Product 1

HCID 189189643,5-Dimethyl-2-[4-(4-nitrobenzoyl)benzyl]thio-4(3H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3,5-dimethyl-2-mercaptoquinazolin-4-one (2.03 g, 9.74 mmol) in EtOH (30.0 ml)-THF (30.0 ml) was added 1N-aqueous sodium hydroxide solution (10.0 ml). Then, 4-(4-nitrobenzoyl)benzyl bromide (3.50 g, 10.9 mmol) was added and the mixture was stirred at room temperature overnight. The solvent was then distilled off and the residue was dissolved in ethyl acetate and washed with saturated aqueous NaCl solution. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized from methanol to provide light-yellow needles.

Workup

  1. distillationThe solvent was then distilled off
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol
  7. customto provide light-yellow needles

Sources & evidence

ORD record
ord-7375db4fad31448b87ff79b5571ff176
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…