Dimethylformamide → 2-[3-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinone

HRID 1291243Notes

Reaction equation

HRID 1291243 reaction equation
[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+].CN(C=O)C.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[CH2:31]Br)=[O:27])=[CH:24][CH:23]=1>C(O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=2)[CH2:31][S:1][C:2]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[O:27])=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 178481666HCID 178481666, compound

Product 1

HCID 189190432-[3-(4-Chlorobenzoyl)benzyl]thio-3-methyl-4(3H)-quinazolinoneYield 101.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-mercapto-3-methyl-4(3H)-quinazolinone (1.0 g) and sodium hydroxide (250 mg) in 50% ethanol (15 ml)-DMF (15 ml) was added 3-(4-chloro-benzoyl)benzyl bromide (1.88 g) and the mixture was stirred at room temperature for 1 hour. This reaction mixtrue was poured in water and the resulting crystals were collected by filtration, rinsed with water and methanol, and recrystallized from methanol to provide the title compound as colorless solid (2.22 g). 1H-NMR (CDCl3) 8: 3.59(3H,s), 4.59(2H,s), 7.34-7.52(5H,m), 7.61-7.80(5H,m), 7.96(1H,d,J=2.0Hz), 8.22(1H,dd,J=8.0,1.4Hz).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washrinsed with water and methanol
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-30e89e1420e14406861d683c91356859
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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