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

HRID 1291370Notes

Reaction equation

HRID 1291370 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][CH2:19][CH2:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1)(=[O:17])[CH3:16].[OH-].[Na+]>CO>[C:15]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:29]=[CH:30][C:31]([CH2:32][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:34][CH:35]=2)=[O:27])=[CH:24][CH:23]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 539921014-(4-Acetoxyethoxybenzoyl)benzyl bromideHCID 178424003HCID 178424003, compound

Product 1

HCID 189190842-[4-[4-(2-Acetoxyethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinoneYield 56.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (1.888 g), 4-(4-acetoxyethoxybenzoyl)benzyl bromide (3.895 g) and 1N-aqueous sodium hydroxide solution (14.3 ml) in methanol (30 ml) was stirred at room temperature for 30 minutes. This reaction mixture was concentrated and extracted with chloroform. The extract was washed with water, dried, and concentrated, and the residue was recrystallized from ethyl acetate to provide the title compound as colorless solid (2.597 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 recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1de94f94b39f45b5aa58dd24cdca121b
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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