Dichloromethane → 3,5-dimethyl-2-[4-[4-(2-hydroxyethoxy)benzoyl]benzylthio]-4(3H)-quinazolinone

HRID 1291371Notes

Reaction equation

HRID 1291371 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:36]=[CH:35][C:11]([C:12]([C:14]2[CH:34]=[CH:33][C:17]([CH2:18][S:19][C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[CH3:32])[N:21]=3)=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1)(=O)C.[OH-].[Na+].ClCCl>CO>[CH3:30][N:29]1[C:28](=[O:31])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[CH3:32])[N:21]=[C:20]1[S:19][CH2:18][C:17]1[CH:33]=[CH:34][C:14]([C:12](=[O:13])[C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][OH:4])=[CH:36][CH:35]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 189190842-[4-[4-(2-Acetoxyethoxy)benzoyl]benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 189188073,5-dimethyl-2-[4-[4-(2-hydroxyethoxy)benzoyl]benzylthio]-4(3H)-quinazolinoneYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[4-[4-(2-acetoxyethoxy)benzoyl]-benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (1.75 g) and 1N-aqueous sodium hydroxide solution (15 ml) in methanol (50 ml)-dichloromethane (25 ml) was stirred at room temperature for 3 hours. This reaction mixture was extracted with dichloromethane and the extract was dried and concentrated. The residue was recrystallized from ethyl acetate to provide the title compound as colorless solid (1.278 g).

Workup

  1. extractionThis reaction mixture was extracted with dichloromethane
  2. customthe extract was dried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ea0dc2c89c7042598e3eba59927e21a7
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…